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Identification
Name Erythromycin
Accession Number DB00199 (APRD00953)
Type small molecule
Groups approved
Descriptio n Erythromycin is a macrolide antibiot ic produced b y Streptomyces erythreus. It inhibits bacterial protein synthesis bybinding to bacterial 50S ribosomal subunits; binding inhibits peptidyl transferase activity and interferes withtranslocation of amino acids during translation and assembly of proteins. Erythromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.
Structure
(http://structures.wishartlab.com/molecules/DB00199/image.png)
Synonyms
Synonym Language Code
3''-O-demethylerythromycin Not Available Not Available
Abomacetin Not Availab le Not Availab le
Erythromycin A Not Available Not Available
Erythromycin C Not Available Not Available
Salts Not Available
Brand names
Name Company
Akne-Mycin Not Availab le
Eryc Not Available
Erygel Not Available
Home (/) Browse (/drugs) Search (/drugs/DB00199) Downloads (/downloads) About (/about)
Help (/ doc ument at ion) Tools ( ht tp: // www. wishart lab. com/ web_servers ) Cont ac t Us ( /c ont ac t)
Identification Taxonom y Pharm acology ADMET Pharm acoeconom ics Properties Spectra References Interactions 0 Com ments
targets (3) (/drugs/DB00199#targets) enzymes (5) (/drugs/DB00199#enzymes ) transporters (4) (/drugs/DB00199#transporters)
Biointeractions (15) (/dru gs/DB00199/biointeracti ons)
MOL (/drugs/DB00199.mol) SDF (/drugs/DB00199.sdf) PDB (/drugs/DB00199.pdb) SMILES (/drugs/DB00199.smiles)
InChI (/drugs/DB00199.inchi) View 2D Structure (/drugs/DB00199/structure) View 3D Structure (/drugs/DB00199/structure?dim=3d)
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http://structures.wishartlab.com/molecules/DB00199/image.pnghttp://www.drugbank.ca/http://www.drugbank.ca/drugshttp://www.drugbank.ca/drugs/DB00199http://www.drugbank.ca/downloadshttp://www.drugbank.ca/abouthttp://www.drugbank.ca/drugs/DB00199/structure?dim=3dhttp://www.drugbank.ca/drugs/DB00199/structurehttp://www.drugbank.ca/drugs/DB00199.inchihttp://www.drugbank.ca/drugs/DB00199.smileshttp://www.drugbank.ca/drugs/DB00199.pdbhttp://www.drugbank.ca/drugs/DB00199.sdfhttp://www.drugbank.ca/drugs/DB00199.molhttp://www.drugbank.ca/drugs/DB00199/biointeractionshttp://www.drugbank.ca/contacthttp://www.wishartlab.com/web_servershttp://www.drugbank.ca/documentationhttp://www.drugbank.ca/abouthttp://www.drugbank.ca/downloadshttp://www.drugbank.ca/drugs/DB00199http://www.drugbank.ca/drugshttp://www.drugbank.ca/http://structures.wishartlab.com/molecules/DB00199/image.pnghttp://v3.drugbank.ca/http://www.drugbank.ca/unearth/q/advanced_search8/12/2019 DrugBank_ Erythromycin (DB00199)
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Ilosone Not Available
Staticin Not Available
T-stat Not Available
Brand mixtures
Brand Name Ingredients
Sans-Acne Solution Alcohol Anhydrous + ErythromycinStaticin Lot Alcohol Anhydrous + Erythromycin + Laureth 4
Stievamycin Forte Gel Erythromycin + Tretinoin
Stievamycin Gel Erythromycin + Tretinoin
T-Stat Lot Alcohol Anhydrous + Erythromycin
T-Stat Pad-Lot Alcohol Anhydrous + Erythromycin
Categories Gastrointestinal Agents (/mesh/gastrointestinal-agents) Anti-Bacterial Agents (/mesh/anti-bacterial-agents)Protein Synthesis Inhibitors (/mesh/protein-synthesis-inhibitors)
CAS number 114-07-8
Weight Average: 733.9268Monoisotopic: 733.461241235
Chemical Formula C H NO
InChI Key InChIKey=ULGZDMOVFRHVEP-RWJQBGPGSA-N
InChI InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1Plain Text (/drugs/DB00199.inchi)
IUPAC Name (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
SMILES CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)OPlain Text (/drugs/DB00199.smiles )
Mass Spec Not Available
Taxonomy
Kingdom Organic Compounds
Superclass Phenylpropanoids and Polyketides
Class Macrolides and Analogues
Subclass Not Available
Direct parent Macrolides and Analogues
Alternative pare nts Dihexoses; O-glycosyl Compounds; Amino Sugars; Oxanes; Tertiary Alcohols; Tertiary Amines; Ketones; 1,2-Diols;Secondary Alcohols; Carboxylic Acid Esters; Polyamines; Acetals
Substituents disaccharide; amino sugar; oxane; saccharide; tertiary alcohol; tertiary amine; 1,2-diol; secondary alcohol; carboxylicacid ester; ketone; polyol; acetal; ether; polyamine; carboxylic acid derivative; carbonyl group; amine; alcohol;organonitrogen compound
Classificationdescription
This compound belongs to the macrolides and analogues. These are organic compounds containing a lactone ring of atleast twelve members.
Pharmacology
Indication For use in the treatment of infections caused by susceptible strains of microorganisms in the following diseases:respiratory tract infections (upper and lower) of mild to moderate degree, pertussis (whooping cough), as adjunct toantitoxin in infections due to Corynebacterium diphtheriae , in the treatment of infections due to Corynebacteriumminutissimum , intestinal amebiasis caused by Entamoeba histolytica , acute pelvic inflammatory disease caused byNeisseria gonorrhoeae , skin and soft tissue infections of mild to moderate severity caused by Streptococcus pyogenes
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http://www.drugbank.ca/drugs/DB00199.smileshttp://www.drugbank.ca/drugs/DB00199.inchihttp://www.drugbank.ca/mesh/protein-synthesis-inhibitorshttp://www.drugbank.ca/mesh/anti-bacterial-agentshttp://www.drugbank.ca/mesh/gastrointestinal-agents8/12/2019 DrugBank_ Erythromycin (DB00199)
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, ,trachomatis , nongonococcal urethritis caused by Ureaplasma urealyticum , and Legionnaires' disease caused byLegionella pneumophila .
Pharmacodynamics Erythromycin is produced by a strain of Streptomyces erythraeus and belongs to the macrolide group of antibiotics. After absorption, erythromycin diffuses readily into most body fluids. In the absence of meningeal inflammation, lowconcentrations are normally achieved in the spinal fluid, but the passage of the drug across the blood-brain barrier increases in meningitis. Erythromycin is excreted in breast milk. The drug crosses the placental barrier with fetal serumdrug levels reaching 5 - 20% of maternal serum concentrations. Erythromycin is not removed by peritoneal dialysis or hemodialysis.
Me chanism of action Erythromycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterialribosomes or near the P or donor site so that binding of tRNA (transfer RNA) to the donor site is blocked.Translocation of peptides from the A or acceptor site to the P or donor site is prevented, and subsequent proteinsynthesis is inhibited. Erythromycin is effective only against actively dividing organisms. The exact mechanism by whicherythmromycin reduces lesions of acne vulgaris is not fully known: however, the effect appears to be due in part to theantibacterial activity of the drug.
Absorption Orally administered erythromycin base and its salts are readily absorbed in the microbiologically active form. Topicalapplication of the ophthalmic ointment to the eye may result in absorption into the cornea and aqueous humor.
Volume of distribution Not Available
Protein binding Erythromycin is largely bound to plasma proteins, ranging from 75 - 95% binding depending on the form.
Metabolism Hepatic. Extensively metabolized - after oral administration, less than 5% of the administered dose can be recoveredin the active form in the urine. Erythromycin is par tially metabolized by CYP3A4 resulting in numerous druginteractions.
Substrate Enzymes
ErythromycinCytochrome P450 3A4(/bio_entities/BE0002638)
norerythromycin(/metabolites/DBMET00365)
Details (/reactions/367)
Route of elimination Not Available
Half life 0.8 - 3 hours
Clearance Not Available
Toxicity Symptoms of overdose include diarrhea, nausea, stomach cramps, and vomiting.
Affected organisms Enteric bacteria and other eubacteria
Pathways Pathway Category SMPDB ID
Erythromycin ActionPathway
Drugaction
SMP00250 (http://www.smpdb.ca/view/SMP00250?reset=true&highlight[DB00199]=true)
SNP Me diated Effects Not Available
SNP Me diatedAdverse DrugReactions
Not Available
ADMETPredicted ADMETfeatures
Property Value Probability
Human Intestinal Absorption + 0.5114
Blood Brain Barrier - 0.9889
Caco-2 permeable - 0.8957
P-glycoprotein substrate Substrate 0.8098
P-glycoprotein inhibitor I Inhibitor 0.8564
P-glycoprotein inhibitor II Non-inhibitor 0.5963
Renal organic cation transporter Non-inhibitor 0.9222
CYP450 2C9 substrate Non-substrate 0.7898
CYP450 2D6 substrate Non-substrate 0.9225
CYP450 3A4 substrate Substrate 0.6528
CYP450 1A2 substrate Non-inhibitor 0.9045
http://www.drugbank.ca/metabolites/DBMET00365http://www.drugbank.ca/bio_entities/BE0002638http://www.smpdb.ca/view/SMP00250?reset=true&highlight[DB00199]=truehttp://www.drugbank.ca/reactions/3678/12/2019 DrugBank_ Erythromycin (DB00199)
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Prepak Systems Inc. (http://www.prepaksys.com)Prescription Dispensing Service Inc.Proter SPAQualitest (http://www.worldoftest.com)Rebel Distributors Corp. (http://www.rebelrx.com)Redpharm DrugRemedy Repack (http://www.remedyrepack.com)Resource Optimization and Innovation LLCSandhills Packaging Inc. (http://www.sandhillspackaging.com)Sandoz (http://www.sandoz.ca)Sanofi-Aventis Inc. (http://www.sanofi-aventis.com)Seneca Pharmaceuticals Inc.Southwood Pharmaceuticals (http://www.southwoodhealthcare.com)St Mary's Medical Park PharmacyStat Rx Usa (http://statrxusa.exporterus.com)Tolmar Inc. (http://www.tolmar.com)Tya PharmaceuticalsValeant Ltd. (http://www.valeant.com)Veratex Corp.Wa Butler Co.Wilson Ophthalmic Corp. (http://www.hilco.com)Wockhardt Ltd. (http://www.wockhardtin.com)X-Gen Pharmaceuticals (http://www.x-gen.us)
Dosage forms
Form Route Strength
Capsule, coated Oral
Liquid Dental
Liquid Oral
Ointment Ophthalmic
Powder Intravenous
Powder Oral
Powder, for solution Intravenous
Powder, for solution Oral
Powder, for suspension Oral
Suspension Oral
Prices
Unit description Cost Unit
Akne-mycin 2% ointment 3.96USD g
Apo-Erythro Base 250 m g Tablet 0.19USD tablet
Apo-Erythro E-C 250 mg Capsule (Enteric-Coated Pell et) 0.41USD capsul e
Apo-Erythro E-C 333 mg Capsule (Enteric-Coated Pell et) 0.45USD capsul e
Apo-Erythro-Es 600 m g Tablet 0.35USD tablet
Apo-Erythro-S 250 mg Table t 0.22USD tablet
Apo-Erythro-S 500 mg Table t 0.57USD tablet
Benzamycin 5-3% Gel 46.6 gm Jar 236.63USD jar
Benzamycin gel 4.95USD g
BenzamycinPak 60 5-3% Packets (2 Box Contains 60 Packets) 142.45USD packet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
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http://www.x-gen.us/http://www.wockhardtin.com/http://www.hilco.com/http://www.valeant.com/http://www.tolmar.com/http://statrxusa.exporterus.com/http://www.southwoodhealthcare.com/http://www.sanofi-aventis.com/http://www.sandoz.ca/http://www.sandhillspackaging.com/http://www.remedyrepack.com/http://www.rebelrx.com/http://www.worldoftest.com/http://www.prepaksys.com/8/12/2019 DrugBank_ Erythromycin (DB00199)
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State solid
ExperimentalProperties
Property Value Source
melting point 191 C PhysProp
water solubility 2000mg/L at 28C European Pharmacopeia
logP 3.06 MCFARLAND,JW ET AL. (1997)
Caco2 permeability -5.43 ADME Research, USCD
pKa 8.88 (at 25 C) MCFARLAND,JW ET AL. (1997)
Predicted Properties Property Value Source
water solubility 4.59e-01 g/l ALOGPS (http://www.vcclab.org/lab/alogps/)
logP 2.37 ALOGPS (http://www.vcclab.org/lab/alogps/)
logP 2.6 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-predictors/#logp_logd)
logS -3.2 ALOGPS (http://www.vcclab.org/lab/alogps/)
pKa (strongest acidic) 12.44 ChemAxon(http://www.chemaxon.com/products/calculator-
plugins/property-predictors/#pka)
pKa (strongest basic) 8.38 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-predictors/#pka)
physiological charge 1 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-predictors/#pka)
hydrogen acceptor count 13 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bond)
hydrogen donor count 5 ChemAxon
(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bond)
polar surface area 193.91 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topolgical_surface)
rotatable bond count 7 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysis)
refractivity 186.04 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#refractivity)
polarizability 78.21 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)
number of rings 3 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysis)
bioavailability 0 ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)
rule of five No ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)
Ghose filter No ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)
http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysishttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#refractivityhttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysishttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#topolgical_surfacehttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bondhttp://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bondhttp://www.chemaxon.com/products/calculator-plugins/property-predictors/#pkahttp://www.chemaxon.com/products/calculator-plugins/property-predictors/#pkahttp://www.chemaxon.com/products/calculator-plugins/property-predictors/#pkahttp://www.vcclab.org/lab/alogps/http://www.chemaxon.com/products/calculator-plugins/property-predictors/#logp_logdhttp://www.vcclab.org/lab/alogps/http://www.vcclab.org/lab/alogps/8/12/2019 DrugBank_ Erythromycin (DB00199)
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Veber's rule No ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)
MDDR-like rule Yes ChemAxon(http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)
Spectra
Spectra Not Available
References
Synthesis Refe rence Takehiro Amano, Masami Goi, Kazuto Sekiuchi, Tomomichi Yoshida, Masahiro Hasegawa, Process for preparingerythromycin A oxime or a salt thereof. U.S. Patent US5274085, issued October , 1966.
US5274085 (https://www.google.com/?tbm=pts#q=5274085&tbm=pts)
General Reference 1. Kanazawa S, Ohkubo T, Sugawara K: The effects of grapefruit juice on the pharmacokinetics of erythromycin.Eur J Clin Pharmacol. 2001 Jan-Feb;56(11):799-803. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11294369)
2. Ogwal S, Xide TU: Bioavailability and stability of erythromycin delayed release tablets. Afr Health Sci. 2001Dec;1(2):90-6. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12789122)
3. Okudaira T, Kotegawa T, Imai H, Tsutsumi K, Nakano S, Ohashi K: Effect of the treatment per iod witherythromycin on cytochrome P450 3A activity in humans. J Clin Pharmacol. 2007 Jul;47(7):871-6. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/17585116)
External Links Resource Link
KEGG Drug D00140 (http://www.genome.jp/dbget-bin/www_bget?drug:D00140)
KEGG Compound C01912 (http://www.genome.jp/dbget-bin/www_bget?cpd:C01912)
PubChemCompound
12560 (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=12560)
PubChemSubstance
46508487 (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508487)
ChemSpider 12041 (http://www.chemspider.com/Chemical-Structure.12041.html)
ChEBI 48923 (http://www.ebi.ac.uk/chebi/searchId.do?chebiId=48923)ChEMBL CHEMBL532 (http://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL532)
TherapeuticTargets Database
DAP000111 (http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000111)
PharmGKB PA449493 (http://www.pharmgkb.org/drug/PA449493)
HET ERY (http://www.ebi.ac.uk/msd-srv/chempdb/cgi-bin/cgi.pl?FUNCTION=getByCode&CODE=ERY)
Drug ProductDatabase
2237041 (http://205.193.93.51/dpdonline/searchRequest.do?din=2237041)
RxList http://www.rxlist.com/cgi/generic/erithrom.htm (http://www.rxlist.com/cgi/generic/erithrom.htm)
Drugs.com http://www.drugs.com/cdi/erythromycin-ointment.html (http://www.drugs.com/cdi/erythromycin-ointment.html)
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ery1163.shtml(http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ery1163.shtml)
Wikipedia Erythromycin (http://en.wikipedia.org/wiki/Erythromycin)
ATC Codes D10AF02D DERMATOLOGICALS (/atc/D)D10 ANTI-ACNE PREPARATIONS (/atc/D10)D10A ANTI-ACNE PREPARATIONS FOR TOPICAL USE (/atc/D10A)D10AF Antiinfectives for treatment of acne (/atc/D10AF)
J01FA01J ANTIINFECTIVES FOR SYSTEMIC USE (/atc/J)J01 ANTIBACTERIALS FOR SYSTEMIC USE (/atc/J01)J01F MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS (/atc/J01F)J01FA Macrolides (/atc/J01FA)
S01AA17S SENSORY ORGANS /atc/S
http://www.drugbank.ca/atc/Shttp://www.drugbank.ca/atc/J01FAhttp://www.drugbank.ca/atc/J01Fhttp://www.drugbank.ca/atc/J01http://www.drugbank.ca/atc/Jhttp://www.drugbank.ca/atc/D10AFhttp://www.drugbank.ca/atc/D10Ahttp://www.drugbank.ca/atc/D10http://www.drugbank.ca/atc/Dhttp://en.wikipedia.org/wiki/Erythromycinhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ery1163.shtmlhttp://www.drugs.com/cdi/erythromycin-ointment.htmlhttp://www.rxlist.com/cgi/generic/erithrom.htmhttp://205.193.93.51/dpdonline/searchRequest.do?din=2237041http://www.ebi.ac.uk/msd-srv/chempdb/cgi-bin/cgi.pl?FUNCTION=getByCode&CODE=ERYhttp://www.pharmgkb.org/drug/PA449493http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP000111http://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL532http://www.ebi.ac.uk/chebi/searchId.do?chebiId=48923http://www.chemspider.com/Chemical-Structure.12041.htmlhttp://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508487http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=12560http://www.genome.jp/dbget-bin/www_bget?cpd:C01912http://www.genome.jp/dbget-bin/www_bget?drug:D00140http://www.ncbi.nlm.nih.gov/pubmed/17585116http://www.ncbi.nlm.nih.gov/pubmed/12789122http://www.ncbi.nlm.nih.gov/pubmed/11294369https://www.google.com/?tbm=pts#q=5274085&tbm=ptshttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarizationhttp://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization8/12/2019 DrugBank_ Erythromycin (DB00199)
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S01 OPHTHALMOLOGICALS (/atc/S01)S01A ANTIINFECTIVES (/atc/S01A)S01AA Antibiotics (/atc/S01AA)
AHFS Code s 34:00.0008:12.12.0452:04.04
PDB Entrie s Not Available
FDA label show (/system/fda_labels/DB00199.pdf?1265922812)(149 KB)MSDS show (/system/msds/DB00199.pdf?1265922748)(73 KB)
Interactions
Drug Interactions Drug
Acenocoumarol(/drugs/DB01418)
The macrolide, erythromycin, may increase the anticoagulant effect of acenocoumarol.
Alfentanil (/drugs/DB00802) The macrolide, erythromycin, may increase the effect and toxicity of alfentanil.
Alprazolam(/drugs/DB00404)
The macrolide, erythromycin, may increase the effect of the benzodiazepine,alprazolam.
Aminophylline(/drugs/DB01223) The macrolide, erythromycin, may increase the effect and toxicity of the theophyllinederivative, aminophylline.
Amiodarone(/drugs/DB01118)
Increased risk of cardiotoxicity and arrhythmias
Anisindione(/drugs/DB01125)
The macrolide, erythromycin, may increase the anticoagulant effect of anisindione.
Aprepitant(/drugs/DB00673)
Erythromycin, a moderate CYP3A4 inhibitor, may increase the effect and toxicity of aprepitant.
Artemether (/drugs/DB06697)
Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Astemizole(/drugs/DB00637)
Increased risk of cardiotoxicity and arrhythmias
Atorvastatin(/drugs/DB01076)
The macrolide, erythromycin, may increase the toxicity of the statin, atorvastatin.
Avanafil (/drugs/DB06237) Co-administration with the moderate CYP3A4 inhibitor erythromycin resulted in anapproximate 3.6-fold increase in AUC0-inf and 2.0- fold increase in Cmax of avanafil.
Bendamustine(/drugs/DB06769)
Decreases metabolism, thus decreasing the effects of bendamustine.
Bretylium (/drugs/DB01158) Increased risk of cardiotoxicity and arryhthmias
Bromazepam(/drugs/DB01558)
Erythromcyin may increase the serum concentration of bromazepam by decreasing itsmetabolism. Consider alternate therapy or monitor for changes in the therapeutic and
adverse effects of bromazepam if erythromycin is initiated, discontinued or dosechanged. Dosage adjustments may be required.
Bromocriptine(/drugs/DB01200)
Erythromycin increases serum levels of bromocriptine
Buspirone(/drugs/DB00490)
The macrolide, erythromycin, may increase the effect and toxicity of buspirone.
Cabergoline(/drugs/DB00248)
Erythromycin increases serum levels and toxicity of cabergoline
Carbamazepine(/drugs/DB00564)
The macrolide, erythromycin, may increase the effect of carbamazepine.
Cerivastatin(/drugs/DB00439)
The macrolide, erythromycin, may increase the toxicity of the statin, cerivastatin.
Cilostazol (/drugs/DB01166) Erythromycin increases the effect of cilostazol
Cinacalcet(/drugs/DB01012)
The macrolide, erythromycin, may increase the serum concentration and toxicity of cinacalcet.
Cisapride (/drugs/DB00604) Increased risk of cardiotoxicity and arrhythmias
http://www.drugbank.ca/drugs/DB00604http://www.drugbank.ca/drugs/DB01012http://www.drugbank.ca/drugs/DB01166http://www.drugbank.ca/drugs/DB00439http://www.drugbank.ca/drugs/DB00564http://www.drugbank.ca/drugs/DB00248http://www.drugbank.ca/drugs/DB00490http://www.drugbank.ca/drugs/DB01200http://www.drugbank.ca/drugs/DB01558http://www.drugbank.ca/drugs/DB01158http://www.drugbank.ca/drugs/DB06769http://www.drugbank.ca/drugs/DB06237http://www.drugbank.ca/drugs/DB01076http://www.drugbank.ca/drugs/DB00637http://www.drugbank.ca/drugs/DB06697http://www.drugbank.ca/drugs/DB00673http://www.drugbank.ca/drugs/DB01125http://www.drugbank.ca/drugs/DB01118http://www.drugbank.ca/drugs/DB01223http://www.drugbank.ca/drugs/DB00404http://www.drugbank.ca/drugs/DB00802http://www.drugbank.ca/drugs/DB01418http://www.drugbank.ca/system/msds/DB00199.pdf?1265922748http://www.drugbank.ca/system/fda_labels/DB00199.pdf?1265922812http://www.drugbank.ca/atc/S01AAhttp://www.drugbank.ca/atc/S01Ahttp://www.drugbank.ca/atc/S01http://www.drugbank.ca/atc/S8/12/2019 DrugBank_ Erythromycin (DB00199)
10/18
3/3/2014 DrugBank: Erythromycin (DB00199)
http://www.drugbank.ca/drugs/DB00199 10/18
Citalopram(/drugs/DB00215)
Possible serotoninergic syndrome with this combination
Clozapine(/drugs/DB00363)
Erythromycin increases the effect of clozapine
Colchicine(/drugs/DB01394)
Severe colchicine toxicity can occur
Cyclosporine(/drugs/DB00091)
The macrolide, erythromycin, may increase the effect of cyclosporine.
Diazepam(/drugs/DB00829)
The macrolide, erythromycin, may increase the effect of the benzodiazepine, diazepam.
Dicoumarol(/drugs/DB00266)
The macrolide, erythromycin, may increase the anticoagulant effect of dicumarol..
Digoxin (/drugs/DB00390) The macrolide, erythromycin, may increase the effect of digoxin in 10% of patients.
Dihydroergotamine(/drugs/DB00320)
Possible ergotism and severe ischemia with this combination
Disopyramide(/drugs/DB00280)
Increased risk of cardiotoxicity and arrhythmias
Docetaxel(/drugs/DB01248)
Erythromycin may increase the serum levels and toxicity of docetaxel.
Dofetilide (/drugs/DB00204) Increased risk of cardiotoxicity and arrhythmias
Dyphylline(/drugs/DB00651)
The macrolide, erythromycin, may increase the effect and toxicity of the theophyllinederivative, dyphylline.
Eletriptan (/drugs/DB00216) The macrolide, erythromycin, may increase the effect and toxicity of eletriptan.
Eltrombopag(/drugs/DB06210)
Affects hepatic CYP1A2 metabolism, increases Eltrombopag level or affect.
Eplerenone(/drugs/DB00700)
This CYP3A4 inhibitor increases the effect and toxicity of eplerenone
Ergonovine(/drugs/DB01253)
Possible ergotism and severe ischemia with this combination
Ergotamine(/drugs/DB00696)
Possible ergotism and severe ischemia with this combination
Erlotinib (/drugs/DB00530) This CYP3A4 inhibitor increases levels/toxicity of erlotinib
Everolimus(/drugs/DB01590)
The macrolide, erythromycin, may increase the serum concentration and toxicity of everolimus.
Felodipine(/drugs/DB01023)
Erythromycin increases the effect of felodipine
Fluoxetine(/drugs/DB00472)
Possible serotoninergic syndrome with this combination
Gefitinib (/drugs/DB00317) This CYP3A4 inhibitor increases levels/toxicity of gefitinib
Grepafloxacin(/drugs/DB00365)
Increased risk of cardiotoxicity and arrhythmias
Imatinib (/drugs/DB00619) The macrolide, erythromycin, may increase the serum concentration of imatinib.
Indacaterol(/drugs/DB05039)
Strong inhibitors of CYP3A4 may increase levels of indacaterol. Monitor closely for adverse events.
Itraconazole(/drugs/DB01167)
The macrolide, erythromycin, may increase the effect and toxicity of itraconazole.
Ivacaftor (/drugs/DB08820) Moderate CYP3A4 inhibitors may increase levels of ivacaftor. Consider dose reduction.
Levofloxacin(/drugs/DB01137)
Increased risk of cardiotoxicity and arrhythmias
Lincomycin(/drugs/DB01627)
Possible antagonism of action with this combination.
Lovastatin(/drugs/DB00227)
The macrolide, erythromycin, may increase the toxicity of the statin, lovastatin.
http://www.drugbank.ca/drugs/DB00227http://www.drugbank.ca/drugs/DB01627http://www.drugbank.ca/drugs/DB01137http://www.drugbank.ca/drugs/DB08820http://www.drugbank.ca/drugs/DB01167http://www.drugbank.ca/drugs/DB05039http://www.drugbank.ca/drugs/DB00619http://www.drugbank.ca/drugs/DB00365http://www.drugbank.ca/drugs/DB00317http://www.drugbank.ca/drugs/DB00472http://www.drugbank.ca/drugs/DB01023http://www.drugbank.ca/drugs/DB01590http://www.drugbank.ca/drugs/DB00530http://www.drugbank.ca/drugs/DB00696http://www.drugbank.ca/drugs/DB01253http://www.drugbank.ca/drugs/DB00700http://www.drugbank.ca/drugs/DB06210http://www.drugbank.ca/drugs/DB00216http://www.drugbank.ca/drugs/DB00651http://www.drugbank.ca/drugs/DB00204http://www.drugbank.ca/drugs/DB01248http://www.drugbank.ca/drugs/DB00280http://www.drugbank.ca/drugs/DB00320http://www.drugbank.ca/drugs/DB00390http://www.drugbank.ca/drugs/DB00266http://www.drugbank.ca/drugs/DB00829http://www.drugbank.ca/drugs/DB00091http://www.drugbank.ca/drugs/DB01394http://www.drugbank.ca/drugs/DB00363http://www.drugbank.ca/drugs/DB002158/12/2019 DrugBank_ Erythromycin (DB00199)
11/18
3/3/2014 DrugBank: Erythromycin (DB00199)
http://www.drugbank.ca/drugs/DB00199 11/18
Lumefantrine(/drugs/DB06708)
Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Mesoridazine(/drugs/DB00933)
Increased risk of cardiotoxicity and arrhythmias
Methylergometrine(/drugs/DB00353)
Possible ergotism and severe ischemia with this combination
Methylprednisolone(/drugs/DB00959)
The macrolide, erythromycin, may increase the effect of corticosteroid,methylprednisolone.
Methysergide(/drugs/DB00247)
Possible ergotism and severe ischemia with this combination
Midazolam(/drugs/DB00683)
The macrolide, erythromycin, may increase the effect of the benzodiazepine,midazolam.
Moxifloxacin(/drugs/DB00218)
Increased risk of cardiotoxicity and arrhythmias
Oxtriphylline(/drugs/DB01303)
The macrolide, erythromycin, may increase the effect and toxicity of the theophyllinederivative, oxtriphylline.
Pazopanib(/drugs/DB06589)
Affects CYP3A4 metabolism therefore will decrease levels or effect of pazopanib.Consider alternate therapy.
Pimozide (/drugs/DB01100) Increased risk of cardiotoxicity and arrhythmiasPitavastatin(/drugs/DB08860)
Erythromycin decreases metabolism of pitavastatin. Do not exceed 1 mg per day of pitavastatin or use alternative therapy.
Quetiapine(/drugs/DB01224)
The macrolide, erythromycin, may increase the effect and toxicity of quetiapine.
Quinidine (/drugs/DB00908) Increased risk of cardiotoxicity and arrhythmias
Quinidine barbiturate(/drugs/DB01346)
Increased risk of cardiotoxicity and arrhythmias
Quinupristin(/drugs/DB01369)
This combination presents an increased risk of toxicity
Ranolazine(/drugs/DB00243)
Increased levels of ranolazine - risk of toxicity
Repaglinide(/drugs/DB00912)
The macrolide, erythromycin, may increase the effect of repaglinide.
Rifabutin (/drugs/DB00615) The rifamycin, rifabutin, may decrease the effect of the macrolide, erythromycin.
Rifampicin(/drugs/DB01045)
The rifamycin, rifampin, may decrease the effect of the macrolide, erythromycin.
Ritonavir (/drugs/DB00503) Increased toxicity of both agents
Roflumilast(/drugs/DB01656)
Increases roflumilast levels.
Saxagliptin(/drugs/DB06335)
Erythromycin is an inhibitor of CYP3A4 which increases exposure of saxagliptin.Decrease dose of saxagliptin to 2.5 mg per day.
Sertraline(/drugs/DB01104)
Possible serotoninergic syndrome with this combination
Sibutramine(/drugs/DB01105)
Erythromycin increases the effect and toxicity of sibutramine
Sildenafil (/drugs/DB00203) The macrolide, erythromycin, may increase the effect and toxicity of sildenafil.
Silodosin (/drugs/DB06207) Erythromycin is a moderate inhibitor of CYP3A4 and inhibits P-glycoprotein thusincreasing the potential for adverse effects
Simvastatin(/drugs/DB00641)
The macrolide, erythromycin, may increase the toxicity of the statin, simvastatin.
Sirolimus (/drugs/DB00877) The macrolide, erythromycin, may increase the serum concentration of sirolimus.
Sotalol (/drugs/DB00489) Increased risk of cardiotoxicity and arrhythmias
Sparfloxacin(/drugs/DB01208)
Increased risk of cardiotoxicity and arrhythmias
http://www.drugbank.ca/drugs/DB00864http://www.drugbank.ca/drugs/DB01208http://www.drugbank.ca/drugs/DB00489http://www.drugbank.ca/drugs/DB00877http://www.drugbank.ca/drugs/DB00641http://www.drugbank.ca/drugs/DB06207http://www.drugbank.ca/drugs/DB00203http://www.drugbank.ca/drugs/DB01105http://www.drugbank.ca/drugs/DB01104http://www.drugbank.ca/drugs/DB06335http://www.drugbank.ca/drugs/DB01656http://www.drugbank.ca/drugs/DB00503http://www.drugbank.ca/drugs/DB01045http://www.drugbank.ca/drugs/DB00615http://www.drugbank.ca/drugs/DB00912http://www.drugbank.ca/drugs/DB00243http://www.drugbank.ca/drugs/DB01369http://www.drugbank.ca/drugs/DB01346http://www.drugbank.ca/drugs/DB00908http://www.drugbank.ca/drugs/DB01224http://www.drugbank.ca/drugs/DB08860http://www.drugbank.ca/drugs/DB01100http://www.drugbank.ca/drugs/DB06589http://www.drugbank.ca/drugs/DB01303http://www.drugbank.ca/drugs/DB00218http://www.drugbank.ca/drugs/DB00683http://www.drugbank.ca/drugs/DB00247http://www.drugbank.ca/drugs/DB00959http://www.drugbank.ca/drugs/DB00353http://www.drugbank.ca/drugs/DB00933http://www.drugbank.ca/drugs/DB067088/12/2019 DrugBank_ Erythromycin (DB00199)
12/18
3/3/2014 DrugBank: Erythromycin (DB00199)
http://www.drugbank.ca/drugs/DB00199 12/18
Tacrolimus(/drugs/DB00864)
Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. The macrolideantibiotic, erythromycin, may also increase the blood concentration of tacrolimus.
Tamsulosin(/drugs/DB00706)
Erythromycin, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Erythromycin is initiated, discontinued, or dose changed.
Telithromycin(/drugs/DB00976)
Telithromycin may reduce clearance of Erythromycin. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Erythromycin if Telithromycinis initiated, discontinued or dose changed.
Terfenadine(/drugs/DB00342)
Increased risk of cardiotoxicity and arrhythmias
Theophylline(/drugs/DB00277)
The macrolide, erythromycin, may increase the effect and toxicity of theophylline.
Thioridazine(/drugs/DB00679)
Increased risk of cardiotoxicity and arrhythmias
Thiothixene(/drugs/DB01623)
May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias.Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Tolvaptan(/drugs/DB06212)
Erythromycin is a moderate inhibitor of CYP3A4 and will considerably increase tolvaptanserum concentrations
Topotecan(/drugs/DB01030)
The p-glycoprotein inhibitor, Erythromycin, may increase the bioavailability of oralTopotecan. A clinically significant effect is also expected with IV Topotecan.Concomitant therapy should be avoided.
Toremifene(/drugs/DB00539)
Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is requiredprior to co-administration.
Tramadol (/drugs/DB00193) Erythromycin may increase Tramadol toxicity by decreasing Tramadol metabolism andclearance.
Trazodone(/drugs/DB00656)
The CYP3A4 inhibitor, Erythromycin , may increase Trazodone efficacy/toxicity bydecreasing Trazodone metabolism and clearance. Monitor for changes in Trazodoneefficacy/toxicity if Erythromycin is initiated, discontinued or dose changed.
Triazolam(/drugs/DB00897)
The macrolide, erythromycin, may increase the effect of the benzodiazepine, triazolam.
Trimipramine(/drugs/DB00726)
Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Valproic Acid(/drugs/DB00313)
The macrolide antibiotic, Erythromycin, may increase the serum concentratin of Valproicacid. Consider alternate therapy or monitor for changes in Valproic acid therapeutic andadverse effects if Erythromycin is initiated, discontinued or dose changed.
Vardenafil(/drugs/DB00862)
Erythromycin, a moderate CYP3A4 inhibitor, may reduce the metabolism and clearanceof vardenafil. Consider alternate therapy or monitor for changes in the therapeutic andadverse effects of vardenafil if erythromycin is initiated, discontinued or dose changed.
Verapamil(/drugs/DB00661) Erythromycin, a moderate CYP3A4 inhibitor, may increase the serum concentration of veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Monitor for changes in the therapeutic/adverse effects of verapamil if erythromycin is initiated,discontinued or dose changed.
Vinblastine(/drugs/DB00570)
Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the vinblastineserum concentration and distribution in certain cells. Consider alternate therapy toavoid vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of vinblastine if erythromycin is initiated, discontinued or dose changed.
Vincristine(/drugs/DB00541)
Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vincristineserum concentration and distribution in certain cells. Consider alternate therapy toavoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Erythromycin is initiated, discontinued or dose changed.
Vinorelbine(/drugs/DB00361)
Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vinorelbineserum concentration and distribution in certain cells. Consider alternate therapy toavoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Erythromycin is initiated, discontinued or dose changed.
Vismodegib(/drugs/DB08828)
P-glycoprotein inhibitors may increase the chance of adverse drug reactions.
http://www.drugbank.ca/drugs/DB08828http://www.drugbank.ca/drugs/DB00361http://www.drugbank.ca/drugs/DB00541http://www.drugbank.ca/drugs/DB00570http://www.drugbank.ca/drugs/DB00661http://www.drugbank.ca/drugs/DB00862http://www.drugbank.ca/drugs/DB00313http://www.drugbank.ca/drugs/DB00726http://www.drugbank.ca/drugs/DB00897http://www.drugbank.ca/drugs/DB00656http://www.drugbank.ca/drugs/DB00193http://www.drugbank.ca/drugs/DB00539http://www.drugbank.ca/drugs/DB01030http://www.drugbank.ca/drugs/DB06212http://www.drugbank.ca/drugs/DB01623http://www.drugbank.ca/drugs/DB00679http://www.drugbank.ca/drugs/DB00277http://www.drugbank.ca/drugs/DB00342http://www.drugbank.ca/drugs/DB00976http://www.drugbank.ca/drugs/DB00706http://www.drugbank.ca/drugs/DB008648/12/2019 DrugBank_ Erythromycin (DB00199)
13/18
3/3/2014 DrugBank: Erythromycin (DB00199)
http://www.drugbank.ca/drugs/DB00199 13/18
Voriconazole(/drugs/DB00582)
Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of erythromycin by decreasing its metabolism. Erythromycin may increase the serumconcentration of voriconazole by decreasing its metabolism. Additive QTc prolongationmay also occur. Consider alternate therapy or monitor for QTc prolongation andchanges in the therapeutic and adverse effects of both agents if concomitant therapy isinitiated, discontinued or dose changed.
Vorinostat(/drugs/DB02546)
Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTcprolongation as this can lead to Torsade de Pointes (TdP).
Warfarin (/drugs/DB00682) The macrolide, erythromycin, may increase the anticoagulant effect of warfarin.
Zafirlukast(/drugs/DB00549)
Erythromycin may decrease the serum concentration and effect of zafirlukast.
Ziprasidone(/drugs/DB00246)
Additive QTc-prolonging effects may increase the risk of severe arrhythmias.Concomitant therapy is contraindicated.
Zopiclone(/drugs/DB01198)
The macrolide antibiotic, erythromycin, may increase the serum concentration of zopiclone. Consider alternate therapy or monitor for changes in the therapeutic andadverse effects of zopiclone if erythromycin is initiated, discontinued or dose changed.
Zuclopenthixol(/drugs/DB01624)
Additive QTc prolongation may occur. Consider alternate therapy or use caution andmonitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Zuclopenthixol acetate
(/drugs/DB08919)
Additive QTc prolongation may occur. Consider alternate therapy or use caution and
monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Zuclopenthixol decanoate(/drugs/DB08920)
Additive QTc prolongation may occur. Consider alternate therapy or use caution andmonitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Food Interactions Avoid alcohol.Take on empty stomach: 1 hour before or 2 hours after meals.Take with a full glass of water Avoid taking with grapefruit juice.
1. 23S rRNA (/bio_entities/BE0004800)
Kind: nucleotideOrganism: Enteric bacteria and other eubacteria
Pharmacological action: yes
Actions: inhibitor
Components
Name UniProt ID Details
References:1. Moazed D, Noller HF: Chloramphenicol , erythromycin, carbomycin and vernamycin B protect overlapping sites in the peptidyl transferase region of 23S
ribosomal RNA. Biochimie. 1987 Aug;69(8):879-84. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/3122849)2. Schlunzen F, Zarivach R, Harms J, Bashan A, Tocilj A, Albrecht R, Yonath A, Franceschi F: Structural basis for the interaction of antibiotics with the peptidyl
transferase centre in eubacteria. Nature. 2001 Oct 25;413(6858):814-21. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11677599)3. Garza-Ramos G, Xiong L, Zhong P, Mankin A: Binding site of m acrolide antibiotics on the ribosome: new res istance mutation identifies a s pecific
interaction of ketolides with rRNA. J Bacteriol. 2001 Dec;183(23):6898-907. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11698379)
2. 50S ribosomal protein L22 (/bio_entities/BE0002464)
Kind: protein
Organism: Escherichia coli O157:H7
Pharmacological action: yes
Actions: inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L22 P61177 Details (/polypeptides/P61177)
http://www.uniprot.org/uniprot/P61177http://www.drugbank.ca/bio_entities/BE0002464http://www.ncbi.nlm.nih.gov/pubmed/11698379http://www.ncbi.nlm.nih.gov/pubmed/11677599http://www.ncbi.nlm.nih.gov/pubmed/3122849http://www.drugbank.ca/bio_entities/BE0004800http://www.drugbank.ca/drugs/DB08920http://www.drugbank.ca/drugs/DB08919http://www.drugbank.ca/drugs/DB01624http://www.drugbank.ca/drugs/DB01198http://www.drugbank.ca/drugs/DB00246http://www.drugbank.ca/drugs/DB00549http://www.drugbank.ca/drugs/DB00682http://www.drugbank.ca/drugs/DB02546http://www.drugbank.ca/drugs/DB00582http://www.drugbank.ca/polypeptides/P611778/12/2019 DrugBank_ Erythromycin (DB00199)
14/18
3/3/2014 DrugBank: Erythromycin (DB00199)
http://www.drugbank.ca/drugs/DB00199 14/18
. .
References:1. Halli ng SM, Jensen AE: Intrinsi c and selected resis tance to antibioti cs binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-Tu2,
efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/17014718)2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibioti cs bound to mutated large ribosom al subunits provide a structural explanation for
resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15851032)3. Rolain JM, Raoult D: Prediction of resi stance to erythromycin in the genus Rickettsia by mutations in L22 ribos omal protein. J Antimicrob Chemother.
2005 Aug;56(2):396-8. Epub 2005 Jul 4. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15996971)4. Cagli ero C, Mouline C, Cloeckaert A, Payot S: Synergy between efflux pump CmeABC and modi fications in ribosomal protei ns L4 and L22 in conferring
macrolide resistance in Campylobacter jejuni and Campylobacter coli. Antimicrob Agents Chemother. 2006 Nov;50(11):3893-6. Epub 2006 Aug 28.Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/16940070)
5. Schlunzen F, Harms JM, Francesch i F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basi s for the antibiotic activity of ketolides and azalides.Structure. 2003 Mar;11(3):329-38. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12623020)
6. Davydova N, Streltsov V, Wilce M, Lilj as A, Garber M: L22 ribos omal protein and effect of its mutation on ribosome res is tance to erythromycin. J Mol Biol .2002 Sep 20;322(3):635-44. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12225755)
3. 50S ribosomal protein L4 (/bio_entities/BE0002465)
Kind: protein
Organism: Escherichia coli O157:H7
Pharmacological action: yes
Actions: inhibitor
Components
Name UniProt ID Details
50S ribosomal protein L4 P60725(http://www.uniprot.org/uniprot/P60725)
Details (/polypeptides/P60725)
References:1. Halli ng SM, Jensen AE: Intrinsi c and selected resis tance to antibioti cs binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-Tu2,
efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/17014718)2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibioti cs bound to mutated large ribosom al subunits provide a structural explanation for
resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15851032)3. OConnor M, Gregory ST, Dahlbe rg AE: Multiple defects in trans lation ass ociated with altered ribosomal protein L4. Nucleic Acids Res . 2004 Oct
27;32(19):5750-6. Print 2004. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15509870)4. Schlunzen F, Harms JM, Francesch i F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basi s for the antibiotic activity of ketolides and azalides.
Structure. 2003 Mar;11(3):329-38. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12623020)
1. Cytochrome P450 3A4 (/bio_entities/BE0002638)
Kind: protein
Organism: Human
Pharmacological action: unknown
Actions: substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A4 P08684(http://www.uniprot.org/uniprot/P08684)
Details (/polypeptides/P08684)
References:1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table (http://medicine.iupui.edu/clinpharm /ddis/table.asp). Indiana University School
of Medicine (2007). Access ed May 28, 2010.2. Preis sner S, Kroll K, Dunkel M, Senger C, Goldsobe l G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preis sne r R: SuperCYP: a comprehens ive
database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database iss ue):D237-43. Epub 2009 Nov 24. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/19934256)
3. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dim ensional-quantitative structure activity relations hip analysis of cytochrome P-450 3A4 subs trates. JPharmacol Exp Ther. 1999 Oct;291(1):424-33. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/10490933)
4. Lexicomp
http://www.ncbi.nlm.nih.gov/pubmed/10490933http://www.ncbi.nlm.nih.gov/pubmed/19934256http://medicine.iupui.edu/clinpharm/ddis/table.asphttp://www.uniprot.org/uniprot/P08684http://www.drugbank.ca/bio_entities/BE0002638http://www.ncbi.nlm.nih.gov/pubmed/12623020http://www.ncbi.nlm.nih.gov/pubmed/15509870http://www.ncbi.nlm.nih.gov/pubmed/15851032http://www.ncbi.nlm.nih.gov/pubmed/17014718http://www.uniprot.org/uniprot/P60725http://www.drugbank.ca/bio_entities/BE0002465http://www.ncbi.nlm.nih.gov/pubmed/12225755http://www.ncbi.nlm.nih.gov/pubmed/12623020http://www.ncbi.nlm.nih.gov/pubmed/16940070http://www.ncbi.nlm.nih.gov/pubmed/15996971http://www.ncbi.nlm.nih.gov/pubmed/15851032http://www.ncbi.nlm.nih.gov/pubmed/17014718http://www.uniprot.org/uniprot/P61177http://www.drugbank.ca/polypeptides/P08684http://www.drugbank.ca/polypeptides/P607258/12/2019 DrugBank_ Erythromycin (DB00199)
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2. Cytochrome P450 3A7 (/bio_entities/BE0003612)
Kind: protein
Organism: Human
Pharmacological action: unknown
Actions: substrate inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A7 P24462(http://www.uniprot.org/uniprot/P24462)
Details (/polypeptides/P24462)
References:1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table (http://medicine.iupui.edu/clinpharm /ddis/table.asp). Indiana University School
of Medicine (2007). Access ed May 28, 2010.
3. Cytochrome P450 3A5 (/bio_entities/BE0002362)
Kind: protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor
Components
Name UniProt ID Details
Cytochrome P450 3A5 P20815(http://www.uniprot.org/uniprot/P20815)
Details (/polypeptides/P20815)
References:1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table (http://medicine.iupui.edu/clinpharm /ddis/table.asp). Indiana University School
of Medicine (2007). Access ed May 28, 2010.
4. Cytochrome P450 1A2 (/bio_entities/BE0002433)
Kind: protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor
Components
Name UniProt ID Details
Cytochrome P450 1A2 P05177(http://www.uniprot.org/uniprot/P05177)
Details (/polypeptides/P05177)
References:1. Preis sner S, Kroll K, Dunkel M, Senger C, Goldsobe l G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preis sne r R: SuperCYP: a comprehens ive
database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database iss ue):D237-43. Epub 2009 Nov 24. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/19934256)
http://www.ncbi.nlm.nih.gov/pubmed/19934256http://www.uniprot.org/uniprot/P05177http://www.drugbank.ca/bio_entities/BE0002433http://medicine.iupui.edu/clinpharm/ddis/table.asphttp://www.uniprot.org/uniprot/P20815http://www.drugbank.ca/bio_entities/BE0002362http://medicine.iupui.edu/clinpharm/ddis/table.asphttp://www.uniprot.org/uniprot/P24462http://www.drugbank.ca/bio_entities/BE0003612http://www.drugbank.ca/polypeptides/P05177http://www.drugbank.ca/polypeptides/P20815http://www.drugbank.ca/polypeptides/P244628/12/2019 DrugBank_ Erythromycin (DB00199)
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5. Cytochrome P450 2B6 (/bio_entities/BE0003549)
Kind: protein
Organism: Human
Pharmacological action: unknown
Actions: substrate
Components
Name UniProt ID Details
Cytochrome P450 2B6 P20813(http://www.uniprot.org/uniprot/P20813)
Details (/polypeptides/P20813)
References:1. Lexicomp
1. Multidrug resistance protein 1 (/bio_entities/BE0001032)
Kind: protein
Organism: Human
Pharmacological action: unknown
Actions: substrate inhibitor inducer
Components
Name UniProt ID Details
Multidrug resistance protein 1 P08183(http://www.uniprot.org/uniprot/P08183)
Details (/polypeptides/P08183)
References:1. Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates o f P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in
human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. Pubm ed (http://www.ncbi.nlm.nih.gov/pubmed/8632764)2. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein ass ays in drug dis covery.
J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/11602674)3. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional
quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/11961113)
4. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of i n vitro P-glycoprotein screening ass ays: recomm endations for their use in drugdiscovery. J Med Chem. 2003 Apr 24;46(9):1716-25. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12699389)
5. Takano M, Hasegawa R, Fukuda T, Yumoto R, Nagai J, Murakami T: Interaction with P-glycoprotein and trans port of erythromycin, midazolam andketoconazole in Caco-2 cells. Eur J Pharmacol. 1998 Oct 9;358(3):289-94. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/9822896)
6. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Demps ey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR:Interrelationship between substrates and inhibi tors of human CYP3A and P-glycoprotein. Pharm Res . 1999 Mar;16(3):408-14. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/10213372)
7. Asakura E, Nakayama H, Sugie M, Zhao YL, Nadai M, Kitaichi K, Shim izu A, Miyoshi M, Takagi K, Takagi K, Hasegawa T: Azithromycin reverses anticancer
drug resis tance and modifies hepatobiliary excretion of doxorubicin in rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):333-9. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/14744620)
8. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol ExpTher. 2002 Oct;303(1):323-32. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/12235267)
9. Dahan A, Sabit H, Amidon GL: The H2 receptor antagonis t nizatidine is a P-glycoprotein subs trate: characterization of its intes tinal epitheli al cell effluxtransport. AAPS J. 2009 Jun;11(2):205-13. Epub 2009 Mar 25. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/19319690)
10. Sun H, Huang Y, Frassetto L, Benet LZ: Effects of uremic toxins on hepatic uptake and metaboli sm of erythromycin. Drug Metab Dispos. 2004Nov;32(11):1239-46. Epub 2004 Jul 30. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/15286055)
2. Multidrug resistance-associated protein 1 (/bio_entities/BE0000785)
Kind: protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor
Components
http://www.drugbank.ca/bio_entities/BE0000785http://www.ncbi.nlm.nih.gov/pubmed/15286055http://www.ncbi.nlm.nih.gov/pubmed/19319690http://www.ncbi.nlm.nih.gov/pubmed/12235267http://www.ncbi.nlm.nih.gov/pubmed/14744620http://www.ncbi.nlm.nih.gov/pubmed/10213372http://www.ncbi.nlm.nih.gov/pubmed/9822896http://www.ncbi.nlm.nih.gov/pubmed/12699389http://www.ncbi.nlm.nih.gov/pubmed/11961113http://www.ncbi.nlm.nih.gov/pubmed/11602674http://www.ncbi.nlm.nih.gov/pubmed/8632764http://www.uniprot.org/uniprot/P08183http://www.drugbank.ca/bio_entities/BE0001032http://www.uniprot.org/uniprot/P20813http://www.drugbank.ca/bio_entities/BE0003549http://www.drugbank.ca/polypeptides/P08183http://www.drugbank.ca/polypeptides/P208138/12/2019 DrugBank_ Erythromycin (DB00199)
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Name UniProt ID Details
Multidrug resistance-associated protein 1 P33527(http://www.uniprot.org/uniprot/P33527)
Details (/polypeptides/P33527)
References:1. Terashi K, Oka M, Soda H, Fukuda M, Kawabata S, Nakatomi K, Shiozawa K, Nakamura T, Tsukamoto K, Noguchi Y, Suenaga M, Tei C, Kohno S:
Interactions of ofloxacin and erythromycin with the multidrug resistance protein (MRP) in MRP-overexpressing human leukemia cells. Antimicrob AgentsChemother. 2000 Jun;44(6):1697-700. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/10817732)
3. Solute carrier organic anion transporter family member 1A2 (/bio_entities/BE0003642)
Kind: protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor
Components
Name UniProt ID Details
Solute carrier organic anion transporter family member 1A2 P46721(http://www.uniprot.org/uniprot/P46721)
Details (/polypeptides/P46721)
References:1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters medi ate the cellular uptake and excretion of
fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. Pubmed (http://www.ncbi.nlm.nih.gov/pubmed/10421612)
4. Solute carrier family 22 member 7 (/bio_entities/BE0003646)
Kind: protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor
Components
Name UniProt ID Details
Solute carrier family 22 member 7 Q9Y694(http://www.uniprot.org/uniprot/Q9Y694)
Details (/polypeptides/Q9Y694)
References:1. Kobayashi Y, Sakai R, Ohshiro N, Ohbayashi M, Kohyama N, Yamam oto T: Poss ible involvement of organic anion transporter 2 on the interaction of
theophylline with erythromycin in the human liver. Drug Metab Dispos. 2005 May;33(5):619-22. Epub 2005 Feb 11. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/15708966)
2. Kobayashi Y, Ohshiro N, Shibus awa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isola tion, characterization and differential geneexpression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12065749)
Comments
Comments
http://www.ncbi.nlm.nih.gov/pubmed/12065749http://www.ncbi.nlm.nih.gov/pubmed/15708966http://www.uniprot.org/uniprot/Q9Y694http://www.drugbank.ca/bio_entities/BE0003646http://www.ncbi.nlm.nih.gov/pubmed/10421612http://www.uniprot.org/uniprot/P46721http://www.drugbank.ca/bio_entities/BE0003642http://www.ncbi.nlm.nih.gov/pubmed/10817732http://www.uniprot.org/uniprot/P33527http://www.drugbank.ca/polypeptides/Q9Y694http://www.drugbank.ca/polypeptides/P46721http://www.drugbank.ca/polypeptides/P335278/12/2019 DrugBank_ Erythromycin (DB00199)
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08
(http://www.metabolomicscentre.ca)
(http://genomealberta.ca) (http://genomebc.ca) (http://genomecanada.ca)
This project is supported by TheMetabolomics Innovation Centre(TMIC)
(http://www.metabolomicscentre.ca/), a nationally-funded research and core facility that supports a wide range of cutting-edge metabolomicstudies. TMIC is funded by Genome Alberta (http://www.genomealberta.ca), Genome British Columbia (http://www.genomebc.ca/), and GenomeCanada (http://www.genomecanada.ca), a not-for-profit organization that is leading Canada's national genomics strategy with $900 million infunding from the federal government.
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