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Identification
NameErythromycin
Accession NumberDB00199  (APRD00953)
Typesmall molecule
Groupsapproved
Description

Erythromycin is a macrolide antibiotic produced by Streptomyces erythreus. It inhibits bacterial protein synthesis by binding to bacterial 50S ribosomal subunits; binding inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins. Erythromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.

Structure
Thumb
Synonyms
SynonymLanguageCode
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dioneNot AvailableNot Available
3''-O-demethylerythromycinNot AvailableNot Available
AbomacetinNot AvailableNot Available
EritromicinaNot AvailableNot Available
ErythromycinNot AvailableNot Available
Erythromycin ANot AvailableNot Available
Erythromycin CNot AvailableNot Available
ErythromycineNot AvailableNot Available
ErythromycinumNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
Akne-MycinAlmirall Hermal
E.E.SNot Available
E.E.S.Not Available
EryNot Available
Ery-PedNot Available
ERY-TABNot Available
ErycHospira
ErygelMerz
Erythra-DermNot Available
IlosoneCipa
ILOTYCINNot Available
StaticinWestwood
T-statWestwood
Brand mixtures
Brand NameIngredients
Sans-Acne SolutionAlcohol Anhydrous + Erythromycin
Staticin LotAlcohol Anhydrous + Erythromycin + Laureth 4
Stievamycin Forte GelErythromycin + Tretinoin
Stievamycin GelErythromycin + Tretinoin
T-Stat LotAlcohol Anhydrous + Erythromycin
T-Stat Pad-LotAlcohol Anhydrous + Erythromycin
Categories
CAS number114-07-8
WeightAverage: 733.9268
Monoisotopic: 733.461241235
Chemical FormulaC37H67NO13
InChI KeyULGZDMOVFRHVEP-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/s1
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)O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassMacrolides and Analogues
SubclassNot Available
Direct parentMacrolides and Analogues
Alternative parentsDihexoses; O-glycosyl Compounds; Amino Sugars; Oxanes; Tertiary Alcohols; Tertiary Amines; Ketones; 1,2-Diols; Secondary Alcohols; Carboxylic Acid Esters; Polyamines; Acetals
Substituentsdisaccharide; amino sugar; oxane; saccharide; tertiary alcohol; tertiary amine; 1,2-diol; secondary alcohol; carboxylic acid ester; ketone; polyol; acetal; ether; polyamine; carboxylic acid derivative; carbonyl group; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
Pharmacology
IndicationFor 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 to antitoxin in infections due to Corynebacterium diphtheriae, in the treatment of infections due to Corynebacterium minutissimum, intestinal amebiasis caused by Entamoeba histolytica, acute pelvic inflammatory disease caused by Neisseria gonorrhoeae, skin and soft tissue infections of mild to moderate severity caused by Streptococcus pyogenes and Staphylococcus aureus, primary syphilis caused by Treponema pallidum, infections caused by Chlamydia trachomatis, nongonococcal urethritis caused by Ureaplasma urealyticum, and Legionnaires' disease caused by Legionella pneumophila.
PharmacodynamicsErythromycin 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, low concentrations 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 serum drug levels reaching 5 - 20% of maternal serum concentrations. Erythromycin is not removed by peritoneal dialysis or hemodialysis.
Mechanism of actionErythromycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterial ribosomes 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 protein synthesis is inhibited. Erythromycin is effective only against actively dividing organisms. The exact mechanism by which erythmromycin reduces lesions of acne vulgaris is not fully known: however, the effect appears to be due in part to the antibacterial activity of the drug.
AbsorptionOrally administered erythromycin base and its salts are readily absorbed in the microbiologically active form. Topical application of the ophthalmic ointment to the eye may result in absorption into the cornea and aqueous humor.
Volume of distributionNot Available
Protein bindingErythromycin 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 recovered in the active form in the urine. Erythromycin is partially metabolized by CYP3A4 resulting in numerous drug interactions.

SubstrateEnzymesProduct
Erythromycin
norerythromycinDetails
Route of eliminationNot Available
Half life0.8 - 3 hours
ClearanceNot Available
ToxicitySymptoms of overdose include diarrhea, nausea, stomach cramps, and vomiting.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategorySMPDB ID
Erythromycin Action PathwayDrug actionSMP00250
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
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
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.923
CYP450 2C19 substrate Non-inhibitor 0.9074
CYP450 3A4 substrate Non-inhibitor 0.5744
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9391
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.9335
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.2296 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9902
hERG inhibition (predictor II) Non-inhibitor 0.8956
Pharmacoeconomics
Manufacturers
  • Hospira inc
  • Parke davis div warner lambert co
  • Warner chilcott inc
  • Abbott laboratories pharmaceutical products div
  • Barr laboratories inc
  • Stiefel laboratories inc
  • Altana inc
  • Merz pharmaceuticals llc
  • Perrigo co
  • Syosset laboratories inc
  • Akorn inc
  • Bausch and lomb pharmaceuticals inc
  • E fougera div altana inc
  • Pharmaderm div altana inc
  • Pharmafair inc
  • Dista products co div eli lilly and co
  • Dow pharmaceutical sciences inc
  • Paddock laboratories inc
  • Taro pharmaceuticals north america inc
  • Bioglan pharma inc
  • Alpharma us pharmaceuticals division
  • Eli lilly and co
  • Perrigo new york inc
  • Wockhardt eu operations (swiss) ag
  • Hi tech pharmacal co inc
  • Westwood squibb pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Orthoneutrogena
  • Versapharm inc
  • Ah robins co
  • Solvay pharmaceuticals
  • Watson laboratories inc
  • Life laboratories inc
  • Lilly research laboratories div eli lilly and co
  • Ross laboratories div abbott laboratories inc
  • Pharmacia and upjohn co
  • Naska pharmacal co inc div rugby darby group cosmetics
  • Wyeth ayerst laboratories
  • Abbott laboratories chemical and agricultural products div
  • Mylan pharmaceuticals inc
  • Elkins sinn div ah robins co inc
  • Abraxis pharmaceutical products
  • Baxter healthcare corp anesthesia and critical care
  • Teva parenteral medicines inc
  • Bristol laboratories inc div bristol myers co
  • Warner chilcott div warner lambert co
  • Lederle laboratories div american cyanamid co
  • Purepac pharmaceutical co
  • Bristol myers squibb co
  • Pfizer laboratories div pfizer inc
Packagers
Dosage forms
FormRouteStrength
Capsule, coatedOral
LiquidDental
LiquidOral
OintmentOphthalmic
PowderIntravenous
PowderOral
Powder, for solutionIntravenous
Powder, for solutionOral
Powder, for suspensionOral
SuspensionOral
TabletOral
Prices
Unit descriptionCostUnit
Benzamycin 5-3% Gel 46.6 gm Jar236.63USDjar
BenzamycinPak 60 5-3% Packets (2 Box Contains 60 Packets)142.45USDpacket
Erythromycin 2% Gel 60 gm Tube46.8USDtube
Erycette 60 2% Pad Box30.99USDbox
Erythromycin 2% Gel 30 gm Tube26.2USDtube
Erythromycin 2% Solution 60ml Bottle26.13USDbottle
Eryderm 2% Solution 60ml Bottle25.99USDbottle
Erythromycin 5 mg/gm Ointment Limited Supply Available.13.99USDtube
Benzamycin gel4.95USDg
Akne-mycin 2% ointment3.96USDg
PCE 500 mg Enteric Coated Tabs3.28USDtab
Pce 500 mg dispertab3.03USDtablet
PCE 333 mg Enteric Coated Tabs2.48USDtab
Erythromycin e.s. powder2.39USDg
Benzamycinpak gel2.37USDgel
Pce 333 mg dispertab2.3USDtablet
Romycin eye ointment1.98USDg
Erythromycin eye ointment1.44USDg
Pms-Erythromycin 0.5 % Ointment1.3USDg
Emgel 2% topical gel1.07USDg
Ery-Tab 500 mg Enteric Coated Tabs0.93USDtab
Ery-tab 500 mg tablet ec0.77USDtablet
Ery-Tab 333 mg Enteric Coated Tabs0.72USDtab
Erythro-rx powder0.72USDg
Erythromycin ec 500 mg tablet0.66USDtablet
Erythromycin Base 500 mg tablet0.61USDtablet
Eryc 333 mg Capsule (Enteric-Coated Pellet)0.6USDcapsule
Apo-Erythro-S 500 mg Tablet0.57USDtablet
E-mycin 333 mg tablet ec0.54USDtablet
Eryc 250 mg Capsule (Enteric-Coated Pellet)0.54USDcapsule
Erythromycin powder0.54USDg
Erythromycin 2% gel0.5USDg
Erythromycin Base 250 mg Enteric Coated Capsule0.5USDcapsule
Erythromycin Base 250 mg tablet0.5USDtablet
Ery-tab ec 500 mg tablet0.46USDtablet
Apo-Erythro E-C 333 mg Capsule (Enteric-Coated Pellet)0.45USDcapsule
Ery-Tab 250 mg Enteric Coated Tabs0.45USDtab
Erythromycin st 500 mg tablet0.44USDtablet
Apo-Erythro E-C 250 mg Capsule (Enteric-Coated Pellet)0.41USDcapsule
Ery-tab 333 mg tablet ec0.4USDtablet
Apo-Erythro-Es 600 mg Tablet0.35USDtablet
Erythromycin 500 mg filmtab0.3USDtablet
Erythrocin 500 mg filmtab0.29USDtablet
Ery-tab 250 mg tablet ec0.27USDtablet
E.e.s. 400 filmtab0.25USDtablet
Erythromycin 250 mg filmtab0.25USDtablet
Erythromycin es 400 mg tablet0.25USDtablet
Apo-Erythro-S 250 mg Tablet0.22USDtablet
Apo-Erythro Base 250 mg Tablet0.19USDtablet
Erythrocin 250 mg filmtab0.16USDtablet
Novo-Rythro Ees 80 mg/ml Suspension0.15USDml
Novo-Rythro Estolate 50 mg/ml Suspension0.13USDml
Novo-Rythro Ees 40 mg/ml Suspension0.1USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point191 °CPhysProp
water solubility2000mg/L at 28°CEuropean Pharmacopeia
logP3.06MCFARLAND,JW ET AL. (1997)
Caco2 permeability-5.43ADME Research, USCD
pKa8.88 (at 25 °C)MCFARLAND,JW ET AL. (1997)
Predicted Properties
PropertyValueSource
water solubility4.59e-01 g/lALOGPS
logP2.37ALOGPS
logP2.6ChemAxon
logS-3.2ALOGPS
pKa (strongest acidic)12.44ChemAxon
pKa (strongest basic)8.38ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count13ChemAxon
hydrogen donor count5ChemAxon
polar surface area193.91ChemAxon
rotatable bond count7ChemAxon
refractivity186.04ChemAxon
polarizability78.21ChemAxon
number of rings3ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Takehiro Amano, Masami Goi, Kazuto Sekiuchi, Tomomichi Yoshida, Masahiro Hasegawa, “Process for preparing erythromycin A oxime or a salt thereof.” U.S. Patent US5274085, issued October, 1966.

US5274085
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
  2. Ogwal S, Xide TU: Bioavailability and stability of erythromycin delayed release tablets. Afr Health Sci. 2001 Dec;1(2):90-6. Pubmed
  3. Okudaira T, Kotegawa T, Imai H, Tsutsumi K, Nakano S, Ohashi K: Effect of the treatment period with erythromycin on cytochrome P450 3A activity in humans. J Clin Pharmacol. 2007 Jul;47(7):871-6. Pubmed
External Links
ResourceLink
KEGG DrugD00140
KEGG CompoundC01912
PubChem Compound12560
PubChem Substance46508487
ChemSpider12041
ChEBI48923
ChEMBLCHEMBL532
Therapeutic Targets DatabaseDAP000111
PharmGKBPA449493
HETERY
Drug Product Database2237041
RxListhttp://www.rxlist.com/cgi/generic/erithrom.htm
Drugs.comhttp://www.drugs.com/cdi/erythromycin-ointment.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ery1163.shtml
WikipediaErythromycin
ATC CodesD10AF02J01FA01S01AA17
AHFS Codes
  • 34:00.00
  • 08:12.12.04
  • 52:04.04
PDB EntriesNot Available
FDA labelshow(149 KB)
MSDSshow(73 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolThe macrolide, erythromycin, may increase the anticoagulant effect of acenocoumarol.
AlfentanilThe macrolide, erythromycin, may increase the effect and toxicity of alfentanil.
AlprazolamThe macrolide, erythromycin, may increase the effect of the benzodiazepine, alprazolam.
AminophyllineThe macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, aminophylline.
AmiodaroneIncreased risk of cardiotoxicity and arrhythmias
AnisindioneThe macrolide, erythromycin, may increase the anticoagulant effect of anisindione.
AprepitantErythromycin, a moderate CYP3A4 inhibitor, may increase the effect and toxicity of aprepitant.
ArtemetherAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
AstemizoleIncreased risk of cardiotoxicity and arrhythmias
AtorvastatinThe macrolide, erythromycin, may increase the toxicity of the statin, atorvastatin.
AvanafilCo-administration with the moderate CYP3A4 inhibitor erythromycin resulted in an approximate 3.6-fold increase in AUC0-inf and 2.0-fold increase in Cmax of avanafil.
BendamustineDecreases metabolism, thus decreasing the effects of bendamustine.
BretyliumIncreased risk of cardiotoxicity and arryhthmias
BromazepamErythromcyin may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bromazepam if erythromycin is initiated, discontinued or dose changed. Dosage adjustments may be required.
BromocriptineErythromycin increases serum levels of bromocriptine
BuspironeThe macrolide, erythromycin, may increase the effect and toxicity of buspirone.
CabergolineErythromycin increases serum levels and toxicity of cabergoline
CarbamazepineThe macrolide, erythromycin, may increase the effect of carbamazepine.
CerivastatinThe macrolide, erythromycin, may increase the toxicity of the statin, cerivastatin.
CilostazolErythromycin increases the effect of cilostazol
CinacalcetThe macrolide, erythromycin, may increase the serum concentration and toxicity of cinacalcet.
CisaprideIncreased risk of cardiotoxicity and arrhythmias
CitalopramPossible serotoninergic syndrome with this combination
ClozapineErythromycin increases the effect of clozapine
ColchicineSevere colchicine toxicity can occur
CyclosporineThe macrolide, erythromycin, may increase the effect of cyclosporine.
DiazepamThe macrolide, erythromycin, may increase the effect of the benzodiazepine, diazepam.
DicoumarolThe macrolide, erythromycin, may increase the anticoagulant effect of dicumarol..
DigoxinThe macrolide, erythromycin, may increase the effect of digoxin in 10% of patients.
DihydroergotaminePossible ergotism and severe ischemia with this combination
DisopyramideIncreased risk of cardiotoxicity and arrhythmias
DocetaxelErythromycin may increase the serum levels and toxicity of docetaxel.
DofetilideIncreased risk of cardiotoxicity and arrhythmias
DyphyllineThe macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, dyphylline.
EletriptanThe macrolide, erythromycin, may increase the effect and toxicity of eletriptan.
EltrombopagAffects hepatic CYP1A2 metabolism, increases Eltrombopag level or affect.
EplerenoneThis CYP3A4 inhibitor increases the effect and toxicity of eplerenone
ErgonovinePossible ergotism and severe ischemia with this combination
ErgotaminePossible ergotism and severe ischemia with this combination
ErlotinibThis CYP3A4 inhibitor increases levels/toxicity of erlotinib
EverolimusThe macrolide, erythromycin, may increase the serum concentration and toxicity of everolimus.
FelodipineErythromycin increases the effect of felodipine
FluoxetinePossible serotoninergic syndrome with this combination
GefitinibThis CYP3A4 inhibitor increases levels/toxicity of gefitinib
GrepafloxacinIncreased risk of cardiotoxicity and arrhythmias
ImatinibThe macrolide, erythromycin, may increase the serum concentration of imatinib.
IndacaterolStrong inhibitors of CYP3A4 may increase levels of indacaterol. Monitor closely for adverse events.
ItraconazoleThe macrolide, erythromycin, may increase the effect and toxicity of itraconazole.
IvacaftorModerate CYP3A4 inhibitors may increase levels of ivacaftor. Consider dose reduction.
LevofloxacinIncreased risk of cardiotoxicity and arrhythmias
LincomycinPossible antagonism of action with this combination.
LovastatinThe macrolide, erythromycin, may increase the toxicity of the statin, lovastatin.
LumefantrineAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
MesoridazineIncreased risk of cardiotoxicity and arrhythmias
MethylergometrinePossible ergotism and severe ischemia with this combination
MethylprednisoloneThe macrolide, erythromycin, may increase the effect of corticosteroid, methylprednisolone.
MethysergidePossible ergotism and severe ischemia with this combination
MidazolamThe macrolide, erythromycin, may increase the effect of the benzodiazepine, midazolam.
MoxifloxacinIncreased risk of cardiotoxicity and arrhythmias
OxtriphyllineThe macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, oxtriphylline.
PazopanibAffects CYP3A4 metabolism therefore will decrease levels or effect of pazopanib. Consider alternate therapy.
PimozideIncreased risk of cardiotoxicity and arrhythmias
PitavastatinErythromycin decreases metabolism of pitavastatin. Do not exceed 1 mg per day of pitavastatin or use alternative therapy.
QuetiapineThe macrolide, erythromycin, may increase the effect and toxicity of quetiapine.
QuinidineIncreased risk of cardiotoxicity and arrhythmias
Quinidine barbiturateIncreased risk of cardiotoxicity and arrhythmias
QuinupristinThis combination presents an increased risk of toxicity
RanolazineIncreased levels of ranolazine - risk of toxicity
RepaglinideThe macrolide, erythromycin, may increase the effect of repaglinide.
RifabutinThe rifamycin, rifabutin, may decrease the effect of the macrolide, erythromycin.
RifampicinThe rifamycin, rifampin, may decrease the effect of the macrolide, erythromycin.
RitonavirIncreased toxicity of both agents
RoflumilastIncreases roflumilast levels.
SaxagliptinErythromycin is an inhibitor of CYP3A4 which increases exposure of saxagliptin. Decrease dose of saxagliptin to 2.5 mg per day.
SertralinePossible serotoninergic syndrome with this combination
SibutramineErythromycin increases the effect and toxicity of sibutramine
SildenafilThe macrolide, erythromycin, may increase the effect and toxicity of sildenafil.
SilodosinErythromycin is a moderate inhibitor of CYP3A4 and inhibits P-glycoprotein thus increasing the potential for adverse effects
SimvastatinThe macrolide, erythromycin, may increase the toxicity of the statin, simvastatin.
SirolimusThe macrolide, erythromycin, may increase the serum concentration of sirolimus.
SotalolIncreased risk of cardiotoxicity and arrhythmias
SparfloxacinIncreased risk of cardiotoxicity and arrhythmias
TacrolimusAdditive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. The macrolide antibiotic, erythromycin, may also increase the blood concentration of tacrolimus.
TamsulosinErythromycin, 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.
TelithromycinTelithromycin may reduce clearance of Erythromycin. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Erythromycin if Telithromycin is initiated, discontinued or dose changed.
TerfenadineIncreased risk of cardiotoxicity and arrhythmias
TheophyllineThe macrolide, erythromycin, may increase the effect and toxicity of theophylline.
ThioridazineIncreased risk of cardiotoxicity and arrhythmias
ThiothixeneMay cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
TolvaptanErythromycin is a moderate inhibitor of CYP3A4 and will considerably increase tolvaptan serum concentrations
TopotecanThe p-glycoprotein inhibitor, Erythromycin, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
ToremifeneAdditive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
TramadolErythromycin may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
TrazodoneThe CYP3A4 inhibitor, Erythromycin , may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Erythromycin is initiated, discontinued or dose changed.
TriazolamThe macrolide, erythromycin, may increase the effect of the benzodiazepine, triazolam.
TrimipramineAdditive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Valproic AcidThe macrolide antibiotic, Erythromycin, may increase the serum concentratin of Valproic acid. Consider alternate therapy or monitor for changes in Valproic acid therapeutic and adverse effects if Erythromycin is initiated, discontinued or dose changed.
VardenafilErythromycin, a moderate CYP3A4 inhibitor, may reduce the metabolism and clearance of vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of vardenafil if erythromycin is initiated, discontinued or dose changed.
VerapamilErythromycin, 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.
VinblastineErythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the vinblastine serum concentration and distribution in certain cells. Consider alternate therapy to avoid vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of vinblastine if erythromycin is initiated, discontinued or dose changed.
VincristineErythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vincristine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Erythromycin is initiated, discontinued or dose changed.
VinorelbineErythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vinorelbine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Erythromycin is initiated, discontinued or dose changed.
VismodegibP-glycoprotein inhibitors may increase the chance of adverse drug reactions.
VoriconazoleVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of erythromycin by decreasing its metabolism. Erythromycin may increase the serum concentration of voriconazole by decreasing its metabolism. Additive QTc prolongation may also occur. Consider alternate therapy or monitor for QTc prolongation and changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose changed.
VorinostatAdditive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
WarfarinThe macrolide, erythromycin, may increase the anticoagulant effect of warfarin.
ZafirlukastErythromycin may decrease the serum concentration and effect of zafirlukast.
ZiprasidoneAdditive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
ZopicloneThe macrolide antibiotic, erythromycin, may increase the serum concentration of zopiclone. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if erythromycin is initiated, discontinued or dose changed.
ZuclopenthixolAdditive 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 acetateAdditive 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 decanoateAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor 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.

Targets

1. 23S rRNA

Kind: nucleotide

Organism: 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
  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
  3. Garza-Ramos G, Xiong L, Zhong P, Mankin A: Binding site of macrolide antibiotics on the ribosome: new resistance mutation identifies a specific interaction of ketolides with rRNA. J Bacteriol. 2001 Dec;183(23):6898-907. Pubmed

2. 50S ribosomal protein L22

Kind: protein

Organism: Escherichia coli O157:H7

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
50S ribosomal protein L22 P61177 Details

References:

  1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics 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
  2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed
  3. Rolain JM, Raoult D: Prediction of resistance to erythromycin in the genus Rickettsia by mutations in L22 ribosomal protein. J Antimicrob Chemother. 2005 Aug;56(2):396-8. Epub 2005 Jul 4. Pubmed
  4. Cagliero C, Mouline C, Cloeckaert A, Payot S: Synergy between efflux pump CmeABC and modifications in ribosomal proteins 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
  5. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and azalides. Structure. 2003 Mar;11(3):329-38. Pubmed
  6. Davydova N, Streltsov V, Wilce M, Liljas A, Garber M: L22 ribosomal protein and effect of its mutation on ribosome resistance to erythromycin. J Mol Biol. 2002 Sep 20;322(3):635-44. Pubmed

3. 50S ribosomal protein L4

Kind: protein

Organism: Escherichia coli O157:H7

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
50S ribosomal protein L4 P60725 Details

References:

  1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics 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
  2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. Pubmed
  3. O’Connor M, Gregory ST, Dahlberg AE: Multiple defects in translation associated with altered ribosomal protein L4. Nucleic Acids Res. 2004 Oct 27;32(19):5750-6. Print 2004. Pubmed
  4. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and azalides. Structure. 2003 Mar;11(3):329-38. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  3. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. Pubmed
  4. Lexicomp

2. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

3. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

4. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Lexicomp

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. Pubmed
  2. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. Pubmed
  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
  4. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. Pubmed
  5. Takano M, Hasegawa R, Fukuda T, Yumoto R, Nagai J, Murakami T: Interaction with P-glycoprotein and transport of erythromycin, midazolam and ketoconazole in Caco-2 cells. Eur J Pharmacol. 1998 Oct 9;358(3):289-94. Pubmed
  6. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. Pubmed
  7. Asakura E, Nakayama H, Sugie M, Zhao YL, Nadai M, Kitaichi K, Shimizu A, Miyoshi M, Takagi K, Takagi K, Hasegawa T: Azithromycin reverses anticancer drug resistance and modifies hepatobiliary excretion of doxorubicin in rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):333-9. Pubmed
  8. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. Pubmed
  9. Dahan A, Sabit H, Amidon GL: The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: characterization of its intestinal epithelial cell efflux transport. AAPS J. 2009 Jun;11(2):205-13. Epub 2009 Mar 25. Pubmed
  10. Sun H, Huang Y, Frassetto L, Benet LZ: Effects of uremic toxins on hepatic uptake and metabolism of erythromycin. Drug Metab Dispos. 2004 Nov;32(11):1239-46. Epub 2004 Jul 30. Pubmed

2. Multidrug resistance-associated protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance-associated protein 1 P33527 Details

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 Agents Chemother. 2000 Jun;44(6):1697-700. Pubmed

3. Solute carrier organic anion transporter family member 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 1A2 P46721 Details

References:

  1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. Pubmed

4. Solute carrier family 22 member 7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 7 Q9Y694 Details

References:

  1. Kobayashi Y, Sakai R, Ohshiro N, Ohbayashi M, Kohyama N, Yamamoto T: Possible 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
  2. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08