Identification

Name
Erythromycin
Accession Number
DB00199  (APRD00953)
Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Description

Erythromycin is an antibiotic drug produced by a strain of Saccharopolyspora erythraea (formerly Streptomyces erythraeus) and belongs to the macrolide group of antibiotics [Label]. It was originally discovered in 1952. Erythromycin is widely used for treating a variety of infections, including those caused by gram-positive bacteria, gram-negative bacteria and many other organisms [14], [Label].

Structure
Thumb
Synonyms
  • 3''-O-demethylerythromycin
  • Abomacetin
  • Eritromicina
  • Erythromycin
  • Erythromycin A
  • Erythromycin C
  • érythromycine
  • Erythromycinum
External IDs
NSC-55929
Product Ingredients
IngredientUNIICASInChI Key
Erythromycin estolateXRJ2P631HP3521-62-8AWMFUEJKWXESNL-JZBHMOKNSA-N
Erythromycin ethylsuccinate1014KSJ86F1264-62-6NSYZCCDSJNWWJL-YXOIYICCSA-N
Erythromycin gluceptate2AY21R0U6423067-13-2ZXBDZLHAHGPXIG-VTXLJDRKSA-N
Erythromycin lactobionate33H58I7GLQ3847-29-8NNRXCKZMQLFUPL-WBMZRJHASA-N
Erythromycin phosphateI8T8KU14X74501-00-2VUEMAFLGEMYXIH-YZPBMOCRSA-N
Erythromycin stearateLXW024X05M643-22-1YAVZHCFFUATPRK-YZPBMOCRSA-N
Erythromycin sulfateKVW9N83AME7184-72-7XTSSJGRRFMNXGO-YZPBMOCRSA-N
Erythromycin thiocyanateY7A95YRI887704-67-8WVRRTEYLDPNZHR-YZPBMOCRSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Akne-mycinOintment20 mg/1gTopicalCoria Laboratories1985-01-102015-06-30Us
E.E.sGranule, for suspension200 mg/5mLOralA S Medication Solutions2011-04-18Not applicableUs
E.E.sGranule, for suspension200 mg/5mLOralArbor Pharmaceuticals, Inc.2011-04-18Not applicableUs
E.E.sGranule, for suspension200 mg/5mLOralArbor Pharmaceuticals, Inc.2011-04-18Not applicableUs
E.E.S.Suspension200 mg/5mLOralUNSPECIFIED2006-06-052006-06-05Us
E.E.S.Granule, for suspension200 mg/5mLOralPhysicians Total Care, Inc.1995-02-012010-12-31Us
E.E.S.Granule, for suspension200 mg/5mLOralAbbvie2010-12-102013-09-01Us
E.E.S.Tablet, film coated400 mg/1OralUNSPECIFIED2006-06-052006-06-05Us
E.E.S.Suspension400 mg/5mLOralUNSPECIFIED2006-06-052006-06-05Us
Ees 600 Tablets 600mgTablet600 mgOralAmdipharm Limited1983-12-312017-06-13Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alti-erythromycin Tab 250mg USPTablet, delayed release250 mgOralAltimed Pharma Inc.1985-12-311999-09-17Canada
E.E.s 400Tablet400 mg/1OralArbor Pharmaceuticals, Inc.2011-05-03Not applicableUs
E.E.s 400Tablet400 mg/1OralPhysicians Total Care, Inc.2011-05-032012-06-30Us
E.E.S.Suspension400 mg/5mLOralPhysicians Total Care, Inc.2000-09-272010-12-31Us
E.E.S.Tablet, film coated400 mg/1OralPd Rx Pharmaceuticals, Inc.2010-12-162016-12-15Us
E.E.S.Tablet, film coated400 mg/1OralPd Rx Pharmaceuticals, Inc.2010-12-162016-12-15Us
ErySolution20 mg/1mLTopicalPerrigo New York Inc2008-07-07Not applicableUs
Ery-TabTablet, delayed release500 mg/1OralPhysicians Total Care, Inc.2004-06-30Not applicableUs
Ery-TabTablet, delayed release250 mg/1OralAbbott1982-03-292012-06-01Us0074 630420180907 15195 116c8bv
Ery-tabTablet, delayed release500 mg/1OralA S Medication Solutions2011-04-18Not applicableUs54569 250820180907 15195 1hktyps
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AktipakErythromycin (30 mg/1g) + Benzoyl peroxide (50 mg/1g)GelTopicalCutanea Life Sciences, Inc.2017-04-10Not applicableUs
BenzamycinErythromycin (30 mg) + Benzoyl peroxide (50 mg)GelTopicalValeant Canada Lp Valeant Canada S.E.C.1996-11-05Not applicableCanada
BenzamycinErythromycin (30 mg/1g) + Benzoyl peroxide (50 mg/1g)KitDermik Laboratories1985-01-012016-01-31Us
BenzamycinErythromycin (30 mg/1g) + Benzoyl peroxide (50 mg/1g)KitValeant Pharmaceuticals North America1984-10-26Not applicableUs
Benzamycin PakErythromycin (30 mg/1g) + Benzoyl peroxide (50 mg/1g)GelTopicalDermik Laboratories2002-01-012014-05-31Us
Benzamycin PakErythromycin (30 mg/1g) + Benzoyl peroxide (50 mg/1g)GelTopicalValeant Pharmaceuticals North America2000-11-272015-02-18Us
ErysolErythromycin (2 %) + Avobenzone (2 %) + Ethanol (75 %) + Octinoxate (7.5 %)GelTopicalGlaxosmithkline Inc1994-12-312015-02-03Canada
Erythromycin and Benzoyl PeroxideErythromycin (30 mg/1g) + Benzoyl peroxide (50 mg/1g)KitTopicalSandoz2004-03-29Not applicableUs
Erythromycin and Benzoyl PeroxideErythromycin (30 mg/1g) + Benzoyl peroxide (50 mg/1g)KitTopicalSandoz2004-03-29Not applicableUs
Erythromycin and Benzoyl PeroxideErythromycin (30 mg/1g) + Benzoyl peroxide (50 mg/1g)KitOceanside Pharmaceuticals1984-10-26Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
MaxitrilErythromycin (0.31 g/0.31g) + Bacitracin zinc (500 [USP'U]/1g)KitTopicalFusion Pharmaceuticals LLC2010-02-082010-09-01Us
MytropheneErythromycin (0.31 g/0.31g) + Bacitracin zinc (500 [USP'U]/1g)KitTopicalFusion Pharmaceuticals LLC2010-05-152012-08-31Us
International/Other Brands
Eryc (Hospira) / Ilosone (Cipa) / Staticin (Westwood) / T-stat (Westwood)
Categories
UNII
63937KV33D
CAS number
114-07-8
Weight
Average: 733.9268
Monoisotopic: 733.461241235
Chemical Formula
C37H67NO13
InChI Key
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/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

Pharmacology

Indication

Erythromycin is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the diseases listed below [Label]:

Respiratory infections

Upper respiratory tract infections of mild to moderate degree caused by Streptococcus pyogenes, Streptococcus pneumoniae, or Haemophilus influenzae (when used concomitantly with adequate doses of sulfonamides, since many strains of H. influenzae are not susceptible to the erythromycin concentrations ordinarily achieved) [Label].

Lower-respiratory tract infections of mild to moderate severity caused by Streptococcus pneumoniae or Streptococcus pyogenes. Listeriosis caused by Listeria monocytogenes [Label].

Pertussis (whooping cough) caused by Bordetella pertussis. Erythromycin is effective in eliminating the organism from the nasopharynx of infected individuals rendering them noninfectious. Some clinical studies suggest that erythromycin may be helpful in the prophylaxis of pertussis in exposed susceptible individuals [Label].

Respiratory tract infections due to Mycoplasma pneumoniae [Label].

Legionnaires’ Disease caused by Legionella pneumophila. Although no controlled clinical efficacy studies have been conducted, in vitro and limited preliminary clinical data suggest that erythromycin may be effective in treating Legionnaires’ Disease [Label].

Diphtheria: Infections due to Corynebacterium diphtheriae, as an adjunct to antitoxin, to prevent establishment of carriers and to eradicate the organism in carriers [Label].

Skin infections

Skin and skin structure infections of mild to moderate severity caused by Streptococcus pyogenes or Staphylococcus aureus (resistant staphylococci may emerge during treatment) [Label].

Erythrasma: In the treatment of infections due to Corynebacterium minutissimum [Label].

Gastrointestinal infections

Intestinal amebiasis caused by Entamoeba histolytica (oral erythromycins only). Extraenteric amebiasis requires treatment with other agents [Label].

Genital infections/STIs

Acute pelvic inflammatory disease caused by Neisseria gonorrhoeae: As an alternative drug in treatment of acute pelvic inflammatory disease caused by N. gonorrhoeae in female patients with a history of sensitivity to penicillin. Patients should have a serologic test for syphilis before receiving erythromycin as treatment of gonorrhea and a follow-up serologic test for syphilis after 3 months [Label].

Syphilis caused by Treponema pallidum: Erythromycin is an alternate choice of treatment for primary syphilis in patients allergic to the penicillins. In treatment of primary syphilis, spinal fluid examinations should be done before treatment and as part of follow-up after therapy [Label].

Chlamydia trachomatis: conjunctivitis of the newborn, pneumonia of infancy, and urogenital infections during pregnancy. When tetracyclines are contraindicated or not tolerated, erythromycin is indicated for the treatment of uncomplicated urethral, endocervical, or rectal infections in adults due to Chlamydia trachomatis [Label].

Nongonnoconnal urethritis: When tetracyclines are contraindicated or not tolerated, erythromycin is indicated for the treatment of nongonococcal urethritis caused by Ureaplasma urealyticum [Label].

Associated Conditions
Pharmacodynamics

Macrolides, such as erythromycin, stop bacterial growth by inhibiting protein synthesis and translation, treating bacterial infections [8]. Erythromycin does not exert effects on nucleic acid synthesis [Label].

This drug has been shown to be active against most strains of the following microorganisms, treating both in vitro and in clinical infections. It is important to perform bacterial susceptibility testing before administering this antibiotic, as resistance is an issue that may affect treatment [Label] :

Gram-positive Organisms:

Corynebacterium diphtheriae, Corynebacterium minutissimum, Listeria monocytogenes, Staphylococcus aureus (resistant organisms may emerge during treatment), Streptococcus pneumoniae, Streptococcus pyogenes

Gram-negative Organisms:

Bordetella pertussis, Legionella pneumophila, Neisseria gonorrhoeae

Other Microorganisms:

Chlamydia trachomatis, Entamoeba histolytica, Mycoplasma pneumoniae, Treponema pallidum, Ureaplasma urealyticum [Label].

Mechanism of action

In order to replicate, bacteria require a specific process of protein synthesis, enabled by ribosomal proteins [9]. Erythromycin acts by inhibition of protein synthesis by binding to the 23S ribosomal RNA molecule in the 50S subunit of ribosomes in susceptible bacterial organisms. It stops bacterial protein synthesis by inhibiting the transpeptidation/translocation step of protein synthesis and by inhibiting the assembly of the 50S ribosomal subunit [Label], [10]. This results in the control of various bacterial infections [13], [Label]. The strong affinity of macrolides, including erythromycin, for bacterial ribosomes, supports their broad‐spectrum antibacterial activities [13].

Many strains of Haemophilus influenzae are resistant to erythromycin alone but are found to be susceptible to erythromycin and sulfonamides used in combination. It is important to note that staphylocci resistant to erythromycin may emerge during a course of erythromycin and/or sulfonamides [Label].

TargetActionsOrganism
A23S rRNA
inhibitor
Enteric bacteria and other eubacteria
NMotilin receptor
agonist
Humans
NPotassium voltage-gated channel subfamily H member 2
inhibitor
Humans
ABacterial 50S Ribosomal SubunitNot Available
Absorption

Orally administered erythromycin stearate is readily and reliably absorbed. Optimal serum levels of erythromycin are reached when it is taken in the fasting state or immediately before meals [15].

Erythromycin is well known for its highly variable bioavailability (18-45%) [6] after oral ingestion and its susceptibility to be degraded under acidic conditions [5].

Volume of distribution

Erythromycin readily diffuses into the majority of body fluids and is found to accumulate in leucocytes [5], [15]. Only low concentrations are usually reached in the spinal fluid, however the passage of erythromycin throughthe blood-brain barrier increases in meningitis, likely due to the presence of inflamed tissues [15].

Protein binding

93% serum protein binding (erythromycin propionate) [7].

Metabolism

Hepatic first-pass metabolism contributes significantly to the total metabolism of erythromycin after oral dosing [11]. After oral administration, less than 5% of the administered dose can be recovered in the active form in the urine and a substantial amount is found in the feces [15]. Erythromycin is partially metabolized by CYP3A enzymes, which results in numerous drug interactions [Label].

Erythromycin is hydrolyzed to anhydro forms (anhydroerythromycin [AHE] and other metabolites), and this process is promoted by acidic conditions. AHE is microbiologically inactive but inhibits drug oxidation by the liver and is therefore considered to be an important factor in erythromycin drug-drug interactions. Acidic conditions in stomach increase the level of AHE, but high levels of AHE were also measured in inflamed tonsils [5].

Route of elimination

In patients with normal hepatic function, erythromycin is concentrated in the liver and excreted in the bile [15]. Less than 5% of the orally administered dose of erythromycin is excreted in active form in the urine [15].

A large proportion of the absorbed drug remains unaccounted for and is presumably metabolized, probably in the liver [15].

Half life

3.5 h [6]

In patients with liver disease, the half-life has been shown to be significantly increased, however, this is of little clinical significance [15].

Clearance

CL (l/h/kg) in healthy subjects: 0.53 ± 0.13 after a 125mg intravenous dose [11] .

Toxicity

Oral LD50, rat: 9272 mg/kg [MSDS].

Overdose:

Symptoms of overdose may include diarrhea, nausea, stomach cramps, and vomiting. In case of overdosage, erythromycin should immediately be discontinued. Prompt elimination of unabsorbed erythromycin should be attempted, and all other appropriate supportive measures should be initiated. Erythromycin is not removed by peritoneal dialysis or hemodialysis [Label].

Hepatotoxicity:

Erythromycin can cause hepatic dysfunction, cholestatic jaundice, and abnormal liver transaminases, particularly when erythromycin estolate is administered [16].

A note on pseudomembranous colitis:

Pseudomembranous colitis has been reported with most antibacterial agents, including erythromycin, and may range in severity from mild to life-threatening. Therefore, the physician should consider this diagnosis in patients who with diarrhea after the administration of antibacterial agents [Label].

Pregnancy:

This drug is classified as pregnancy category B: There is no evidence of teratogenicity or any other adverse effect on reproduction in female rats fed erythromycin base (up to 0.25% of diet) before and during mating, during gestation, and through weaning of two successive litters. There are, however, no adequate and well-controlled studies in pregnant women. Because animal reproduction studies are not always representative of human response, this drug should be used during pregnancy only if it absolutely necessary [Label]. It is important to note that erythromycin estolate is contraindicated in pregnancy [16].

Carcinogenesis, Mutagenesis, Impairment of Fertility:

Long-term oral studies in rats with erythromycin ethylsuccinate and erythromycin base did not show evidence of tumorigenicity. Mutagenicity studies have not been conducted to this date. There was no apparent effect on male or female fertility in rats fed erythromycin (base) at levels up to 0.25% of diet [Label].

Nursing Mothers: Erythromycin appears in breast milk at levels which are approximately 50% of the plasma concentration [15]. Caution should be observed when erythromycin is given to a nursing woman [Label].

Affected organisms
  • Enteric bacteria and other eubacteria
  • Streptococcus pyogenes
  • Haemophilus influenzae
  • Staphylococcus aureus
Pathways
PathwayCategory
Erythromycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Glucose-6-phosphate 1-dehydrogenaseVilleurbanneNot Available1000_1002delACCADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseTorunNot Available1006A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSunderlandNot Available105_107delCATADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseIwatsukiNot Available1081G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSerresNot Available1082C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseTondelaNot Available1084_1101delCTGAACGAGCGCAAGGCCADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseLoma LindaNot Available1089C->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAachenNot Available1089C->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseTenriNot Available1096A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMontpellierNot Available1132G>AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseCalvo MackennaNot Available1138A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseRileyNot Available1139T->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseOlomoucNot Available1141T->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseTomahNot Available1153T->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseLynwoodNot Available1154G->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMadridNot Available1155C->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseIowa, Walter Reed, SpringfieldNot Available1156A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseBeverly Hills, Genova, Iwate, Niigata, YamaguchiNot Available1160G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseHartfordNot Available1162A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenasePrahaNot Available1166A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseKrakowNot Available1175T>CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseWisconsinNot Available1177C->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseNashville, Anaheim, PorticiNot Available1178G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAlhambraNot Available1180G->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseBariNot Available1187C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenasePuerto LimonNot Available1192G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseCovao do LoboNot Available1205C>AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseClinicNot Available1215G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseUtrechtNot Available1225C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSuwalkiNot Available1226C->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseRiversideNot Available1228G->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseJapan, ShinagawaNot Available1229G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseKawasakiNot Available1229G->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMunichNot Available1231A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseGeorgiaNot Available1284C->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSumareNot Available1292T->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseTelti/KobeNot Available1318C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSantiago de Cuba, MoriokaNot Available1339G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseHarimaNot Available1358T->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseFiguera da FozNot Available1366G->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAmiensNot Available1367A>TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseBangkok NoiNot Available1376G->T, 1502T->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseFukayaNot Available1462G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseCampinasNot Available1463G->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseBuenos AiresNot Available1465C>TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseArakawaNot Available1466C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseBrightonNot Available1488_1490delGAAADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseKozukataNot Available159G->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAmsterdamNot Available180_182delTCTADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseNo nameNot Available202G->A, 376A->G, 1264C>GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSwanseaNot Available224T->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseUrayasuNot Available281_283delAGAADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseVancouverNot Available317C->G544C->T592C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMt SinaiNot Available376A->G, 1159C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenasePlymouthNot Available488G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseVolendamNot Available514C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseShinshuNot Available527A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseChikugoNot Available535A->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseTsukuiNot Available561_563delCTCADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenasePedoplis-CkaroNot Available573C>GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSantiagoNot Available593G->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMinnesota, Marion, Gastonia, LeJeuneNot Available637G->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseCincinnatiNot Available637G->T, 1037A->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseHarilaouNot Available648T->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseNorth DallasNot Available683_685delACAADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAsahikawaNot Available695G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseDurhamNot Available713A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseStonybrookNot Available724_729delGGCACTADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseWayneNot Available769C->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAveiroNot Available806G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseCleveland CorumNot Available820G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseLilleNot Available821A>TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseBangkokNot Available825G>CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSugaoNot Available826C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseLa JollaNot Available832T->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseWexhamNot Available833C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenasePiotrkowNot Available851T>CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseWest VirginiaNot Available910G->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseOmiyaNot Available921G->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseNaraNot Available953_976delCCACCAAAGGGTACCTGGAC GACCADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseManhattanNot Available962G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseRehevotNot Available964T->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseHoniaraNot Available99A->G / 1360C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseTokyo, FukushimaNot Available1246G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseChathamNot Available1003G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseFushanNot Available1004C->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenasePartenopeNot Available1052G->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseIerapetraNot Available1057C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAnadiaNot Available1193A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAbenoNot Available1220A->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSurabayaNot Available1291G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenasePawneeNot Available1316G->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseS. AntiocoNot Available1342A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseCassanoNot Available1347G->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseHermoupolisNot Available1347G->C / 1360C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseUnion,Maewo, Chinese-2, KaloNot Available1360C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAndalusNot Available1361G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseCosenzaNot Available1376G->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseCanton, Taiwan- Hakka, Gifu-like, Agrigento-likeNot Available1376G->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseFloresNot Available1387C->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseKaiping, Anant, Dhon, Sapporo-like, WoseraNot Available1388G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseKamogawaNot Available169C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseCostanzoNot Available179T>CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAmazoniaNot Available185C->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSongklanagarindNot Available196T->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseHechiNot Available202G->A / 871G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseNamouruNot Available208T->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseBao LocNot Available352T>CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseCrispimNot Available375G->T, 379G->T383T->C384C>TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAcrokorinthosNot Available376A->G / 463C->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSanta MariaNot Available376A->G / 542A->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAnanindeuaNot Available376A->G / 871G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseVanua LavaNot Available383T->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseValladolidNot Available406C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseBelemNot Available409C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseLiuzhouNot Available442G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseShenzenNot Available473G>AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseTaipei “Chinese- 3”Not Available493A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseToledoNot Available496C>TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseNaoneNot Available497G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseNankangNot Available517T->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMiaoliNot Available519C->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMediterranean, Dallas, Panama‚ Sassari, Cagliari, BirminghamNot Available563C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseCoimbra ShundeNot Available592C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseNilgiriNot Available593G>AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseRadlowoNot Available679C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseRoubaixNot Available811G>CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseHaikouNot Available835A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseChinese-1Not Available835A->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMizushimaNot Available848A>GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseOsakaNot Available853C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseViangchan, JammuNot Available871G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSeoulNot Available916G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseLudhianaNot Available929G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseFarroupilhaNot Available977C->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseChinese-5Not Available1024C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseRignanoNot Available130G>AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseOrissaNot Available131C->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseG6PDNiceNot Available1380G>CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseKamiube, KeelungNot Available1387C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseNeapolisNot Available1400C->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAuresNot Available143T->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSplitNot Available1442C->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseKambosNot Available148C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenasePalestrinaNot Available170G>AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMetapontoNot Available172G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMusashinoNot Available185C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseAsahiNot Available202G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseA- (202), Ferrara INot Available202G->A / 376A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMurcia OristanoNot Available209A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseUbe KonanNot Available241C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseLagosantoNot Available242G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseGuangzhouNot Available274C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseHammersmithNot Available323T->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSinnaiNot Available34G->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseA- (680)Not Available376A->G / 680G->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseA- (968), Betica,Selma, GuantanamoNot Available376A->G / 968T->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSalerno PyrgosNot Available383T>GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseQuing YanNot Available392G->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseLagesNot Available40G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseIleshaNot Available466G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMahidolNot Available487G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMalagaNot Available542A->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSibariNot Available634A->GADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMexico CityNot Available680G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseNanningNot Available703C->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseSeattle, Lodi, Modena, Ferrara II, Athens-likeNot Available844G->CADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseBajo MaumereNot Available844G->TADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseMontalbanoNot Available854G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseKalyan-Kerala, Jamnaga, RohiniNot Available949G->AADR InferredIncreased risk of dose-related hemolysis.Details
Glucose-6-phosphate 1-dehydrogenaseGaoheNot Available95A->GADR InferredIncreased risk of dose-related hemolysis.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Erythromycin.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Erythromycin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Erythromycin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Erythromycin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Erythromycin.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Erythromycin.
6-Deoxyerythronolide BThe metabolism of Erythromycin can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Erythromycin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Erythromycin.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Erythromycin.
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.

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 References
  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:11294369]
  2. Ogwal S, Xide TU: Bioavailability and stability of erythromycin delayed release tablets. Afr Health Sci. 2001 Dec;1(2):90-6. [PubMed:12789122]
  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:17585116]
  4. Houin G, Tillement JP, Lhoste F, Rapin M, Soussy CJ, Duval J: Erythromycin pharmacokinetics in man. J Int Med Res. 1980;8 Suppl 2:9-14. [PubMed:7429008]
  5. Krasniqi S, Matzneller P, Kinzig M, Sorgel F, Huttner S, Lackner E, Muller M, Zeitlinger M: Blood, tissue, and intracellular concentrations of erythromycin and its metabolite anhydroerythromycin during and after therapy. Antimicrob Agents Chemother. 2012 Feb;56(2):1059-64. doi: 10.1128/AAC.05490-11. Epub 2011 Nov 14. [PubMed:22083477]
  6. Amsden GW: Erythromycin, clarithromycin, and azithromycin: are the differences real? Clin Ther. 1996 Jan-Feb;18(1):56-72; discussion 55. [PubMed:8851453]
  7. Gordon RC, Regamey C, Kirby WM: Serum protein binding of erythromycin, lincomycin, and clindamycin. J Pharm Sci. 1973 Jul;62(7):1074-7. [PubMed:4714113]
  8. Fohner AE, Sparreboom A, Altman RB, Klein TE: PharmGKB summary: Macrolide antibiotic pathway, pharmacokinetics/pharmacodynamics. Pharmacogenet Genomics. 2017 Apr;27(4):164-167. doi: 10.1097/FPC.0000000000000270. [PubMed:28146011]
  9. Champney WS, Burdine R: Macrolide antibiotics inhibit 50S ribosomal subunit assembly in Bacillus subtilis and Staphylococcus aureus. Antimicrob Agents Chemother. 1995 Sep;39(9):2141-4. [PubMed:8540733]
  10. Champney WS, Miller M: Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin. Curr Microbiol. 2002 Jun;44(6):418-24. [PubMed:12000992]
  11. Sun H, Frassetto LA, Huang Y, Benet LZ: Hepatic clearance, but not gut availability, of erythromycin is altered in patients with end-stage renal disease. Clin Pharmacol Ther. 2010 Apr;87(4):465-72. doi: 10.1038/clpt.2009.247. Epub 2010 Jan 20. [PubMed:20090676]
  12. Franke RM, Lancaster CS, Peer CJ, Gibson AA, Kosloske AM, Orwick SJ, Mathijssen RH, Figg WD, Baker SD, Sparreboom A: Effect of ABCC2 (MRP2) transport function on erythromycin metabolism. Clin Pharmacol Ther. 2011 May;89(5):693-701. doi: 10.1038/clpt.2011.25. Epub 2011 Mar 30. [PubMed:21451505]
  13. Dinos GP: The macrolide antibiotic renaissance. Br J Pharmacol. 2017 Sep;174(18):2967-2983. doi: 10.1111/bph.13936. Epub 2017 Aug 10. [PubMed:28664582]
  14. NIH StatPearls: Erythromycin [Link]
  15. MedSafe Data Sheet: ERA film tabs [File]
  16. Erythromycin estolate monograph [File]
External Links
Human Metabolome Database
HMDB0014344
KEGG Drug
D00140
KEGG Compound
C01912
PubChem Compound
12560
PubChem Substance
46508487
ChemSpider
12041
BindingDB
50344942
ChEBI
42355
ChEMBL
CHEMBL532
Therapeutic Targets Database
DAP000111
PharmGKB
PA449493
HET
ERY
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Erythromycin
ATC Codes
J01FA01 — ErythromycinD10AF02 — ErythromycinS01AA17 — ErythromycinD10AF52 — Erythromycin, combinations
AHFS Codes
  • 52:04.04 — Antibacterials
  • 08:12.12.04 — Erythromycins
PDB Entries
1jzy / 1yi2 / 2iyf / 2j0d / 3aoc / 3frq / 3j5l / 3j7z / 4m83 / 4v7u
show 13 more
FDA label
Download (149 KB)
MSDS
Download (82.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableCardiology: RR / QT1
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceDiabetes, Diabetes Mellitus Type 11
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic SciencePharmacokinetics1
1CompletedTreatmentB-Cell Chronic Lymphocytic Leukemia1
1CompletedTreatmentHealthy Volunteers / Impaired Renal Function1
1CompletedTreatmentHepatitis C Virus (HCV) Infection1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2TerminatedTreatmentAlbinism, Oculocutaneous / Hermansky-Pudlak Syndrome (HPS) / Metabolic Diseases / Platelet Storage Pool Deficiency / Pulmonary Fibrosis1
2CompletedPreventionMalignant Neoplasm of Stomach / Subtotal Gastrectomy1
2CompletedPreventionRas-wildtype Colorectal Cancer1
2CompletedTreatmentAspiration of Gastric Contents / Gastric Emptying1
2CompletedTreatmentBulimia Nervosa (BN) / Eating Disorders1
2CompletedTreatmentChlamydia Trachomatis Infection in Pregnancy1
2TerminatedTreatmentGastroparesis2
2, 3CompletedSupportive CareHealthy Volunteers1
2, 3TerminatedTreatmentCommunity-Acquired Bacterial Pneumonia (CABP)1
2, 3Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3Active Not RecruitingTreatmentHaematemesis / Hemorrhage, Gastrointestinal1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionMumps / Rubella / Rubeola1
3CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
3CompletedTreatmentPreterm Premature Rupture of the Membranes1
3RecruitingTreatmentPreterm Premature Rupture of Membranes (PPROM)1
3Unknown StatusTreatmentEpidermolysis Bullosa1
3WithdrawnPreventionPreterm Premature Ruptured Membranes1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedTreatmentAcute Obliterating Bronchiolitis / Obliterative Bronchiolitis1
4CompletedTreatmentAsthma Bronchial1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentPancreatitis1
4CompletedTreatmentBacterial blepharitis1
4Enrolling by InvitationBasic ScienceBMI >30 kg/m2 / Healthy Volunteers1
4Not Yet RecruitingBasic ScienceHealthy Volunteers1
4Not Yet RecruitingTreatmentFAP-Familial Adenomatous Polyposis1
4RecruitingPreventionAntibiotic Allergy / Antibiotic Side Effect / Eyelid Diseases / Eyelid; Wound / Infection, Postoperative Wound / Skin Cancer Face / Surgical Incision / Surgical Site Infections / Surgical Wound, Recent1
4Unknown StatusTreatmentFAP-Familial Adenomatous Polyposis1
Not AvailableCompletedNot AvailableBronchiectasis1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedBasic SciencePregnancy1
Not AvailableCompletedDiagnosticColorectal Cancer Screening1
Not AvailableCompletedTreatmentLevodopa / Parkinson's Disease (PD)1
Not AvailableCompletedTreatmentLiver Cirrhosis1
Not AvailableCompletedTreatmentVariceal Bleeding1
Not AvailableNot Yet RecruitingNot AvailableCommunity Acquired Pneumonia (CAP)1
Not AvailableNot Yet RecruitingPreventionColostomy Stoma / Hirschprung's Disease / Ileostomy - Stoma / Inflammatory Bowel Diseases (IBD) / Intestinal Obstruction / Jejunostomy Stoma / Meconium Ileus / NEC1
Not AvailableRecruitingNot AvailableChildren; Infection / Newborn; Infection1
Not AvailableRecruitingPreventionRectal Carcinoma1
Not AvailableRecruitingSupportive CareSevere Stroke / Stroke, Acute / Swallowing Disorders1
Not AvailableTerminatedPreventionLength of Pregnancy Prolongation in Hours1
Not AvailableTerminatedTreatmentFeeding Disorder / Infants, Premature / Nutrition Disorder1
Not AvailableTerminatedTreatmentUpper Gastrointestinal Hemorrhage1
Not AvailableUnknown StatusTreatmentApnea / Bradycardia / Reflux, Gastroesophageal1
Not AvailableUnknown StatusTreatmentHepatic Encephalopathy / Liver Cirrhosis / Portal Hypertension1
Not AvailableUnknown StatusTreatmentPneumonia1

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
  • Abbott Laboratories Ltd.
  • Advanced Pharmaceutical Services Inc.
  • Akorn Inc.
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Barr Pharmaceuticals
  • Bausch & Lomb Inc.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Casa De Amigos Pharmacy
  • Central Texas Community Health Centers
  • Community Action Inc. Community Health Services
  • Comprehensive Consultant Services Inc.
  • Contract Pharm
  • Core Pharmaceuticals
  • Coria Laboratories
  • Darby Dental Supply Co. Inc.
  • Dept Health Central Pharmacy
  • Dermik Labs
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DPT Laboratories Ltd.
  • DRX Pharmaceuticals
  • E. Fougera and Co.
  • Eli Lilly & Co.
  • Eye Care and Cure Corp.
  • Eye Supply Usa Inc.
  • Fera Pharmaceuticals
  • H.J. Harkins Co. Inc.
  • Hospira Inc.
  • Inyx Usa Ltd.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Mayne Pharma International Pty Ltd.
  • Medical Ophthalmics
  • Medicis Pharmaceutical Co.
  • Medisca Inc.
  • Medvantx Inc.
  • Merz Pharmaceuticals LLC
  • Mississippi State Dept Health
  • Murfreesboro Pharmaceutical Nursing Supply
  • MWI Veterinary Supply Co.
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Nycomed Inc.
  • Ocusoft
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Paddock Labs
  • Palmetto Pharmaceuticals Inc.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmaceutical Corporation of America
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacia Inc.
  • Pharmaderm
  • Pharmedix
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Polfa
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescription Dispensing Service Inc.
  • Proter SPA
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Sandoz
  • Sanofi-Aventis Inc.
  • Seneca Pharmaceuticals Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Tolmar Inc.
  • Tya Pharmaceuticals
  • Valeant Ltd.
  • Veratex Corp.
  • Wa Butler Co.
  • Wilson Ophthalmic Corp.
  • Wockhardt Ltd.
  • X-Gen Pharmaceuticals
Dosage forms
FormRouteStrength
OintmentTopical20 mg/1g
Tablet, delayed releaseOral250 mg
GelTopical
Kit
Granule, for suspensionOral200 mg/5mL
Tablet, film coatedOral400 mg/1
Powder, for suspensionOral40 mg
TabletOral200 mg
Powder, for suspensionOral400 mg
Tablet, delayed releaseOral250 mg/1
Tablet, delayed releaseOral333 mg/1
Tablet, delayed releaseOral500 mg/1
Capsule, coated pelletsOral250 mg/1
Capsule, delayed release pelletsOral250 mg/1
Capsule, delayed releaseOral250 mg
Capsule, delayed releaseOral333 mg
SuspensionOral200 mg/5mL
SuspensionOral400 mg/5mL
WaferOral200 mg/1
TabletOral600 mg
TabletOral250 mg
TabletOral500 mg
Powder, for solutionIntravenous1 g
Powder, for solutionIntravenous500 mg
Injection, powder, for solutionIntravenous1 g/1
Injection, powder, lyophilized, for solutionIntravenous1 g/20mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/100mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/10mL
LiquidOral50 mg
LiquidOral25 mg
Capsule, delayed releaseOral250 mg/1
GelTopical20 mg/1g
OintmentOphthalmic5 mg/1g
SolutionTopical20 mg/1mL
SolutionTopical20 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
TabletOral400 mg/1
Granule, for suspensionOral
CapsuleOral250 mg
SuspensionOral125 mg
OintmentOphthalmic0.5 mg/1g
OintmentOphthalmic.5 %
KitTopical
SuspensionOral250 mg
PowderOral400 mg
Powder, for solutionOral100 mg
Powder, for solutionOral200 mg
OintmentOphthalmic5 mg
TabletOral333 mg
TabletOral333 mg/1
TabletOral500 mg/1
Powder, for suspensionOral
SolutionTopical
SolutionTopical15 mg/1mL
LotionTopical
Lotion; swabTopical
Prices
Unit descriptionCostUnit
Benzamycin 5-3% Gel 46.6 gm Jar236.63USD jar
BenzamycinPak 60 5-3% Packets (2 Box Contains 60 Packets)142.45USD packet
Erythromycin 2% Gel 60 gm Tube46.8USD tube
Erycette 60 2% Pad Box30.99USD box
Erythromycin 2% Gel 30 gm Tube26.2USD tube
Erythromycin 2% Solution 60ml Bottle26.13USD bottle
Eryderm 2% Solution 60ml Bottle25.99USD bottle
Erythromycin 5 mg/gm Ointment Limited Supply Available.13.99USD tube
Benzamycin gel4.95USD g
Akne-mycin 2% ointment3.96USD g
PCE 500 mg Enteric Coated Tabs3.28USD tab
Pce 500 mg dispertab3.03USD tablet
PCE 333 mg Enteric Coated Tabs2.48USD tab
Erythromycin e.s. powder2.39USD g
Benzamycinpak gel2.37USD gel
Pce 333 mg dispertab2.3USD tablet
Romycin eye ointment1.98USD g
Erythromycin eye ointment1.44USD g
Pms-Erythromycin 0.5 % Ointment1.3USD g
Emgel 2% topical gel1.07USD g
Ery-Tab 500 mg Enteric Coated Tabs0.93USD tab
Ery-tab 500 mg tablet ec0.77USD tablet
Ery-Tab 333 mg Enteric Coated Tabs0.72USD tab
Erythro-rx powder0.72USD g
Erythromycin ec 500 mg tablet0.66USD tablet
Erythromycin Base 500 mg tablet0.61USD tablet
Eryc 333 mg Capsule (Enteric-Coated Pellet)0.6USD capsule
Apo-Erythro-S 500 mg Tablet0.57USD tablet
E-mycin 333 mg tablet ec0.54USD tablet
Eryc 250 mg Capsule (Enteric-Coated Pellet)0.54USD capsule
Erythromycin powder0.54USD g
Erythromycin 2% gel0.5USD g
Erythromycin Base 250 mg Enteric Coated Capsule0.5USD capsule
Erythromycin Base 250 mg tablet0.5USD tablet
Ery-tab ec 500 mg tablet0.46USD tablet
Apo-Erythro E-C 333 mg Capsule (Enteric-Coated Pellet)0.45USD capsule
Ery-Tab 250 mg Enteric Coated Tabs0.45USD tab
Erythromycin st 500 mg tablet0.44USD tablet
Apo-Erythro E-C 250 mg Capsule (Enteric-Coated Pellet)0.41USD capsule
Ery-tab 333 mg tablet ec0.4USD tablet
Apo-Erythro-Es 600 mg Tablet0.35USD tablet
Erythromycin 500 mg filmtab0.3USD tablet
Erythrocin 500 mg filmtab0.29USD tablet
Ery-tab 250 mg tablet ec0.27USD tablet
E.e.s. 400 filmtab0.25USD tablet
Erythromycin 250 mg filmtab0.25USD tablet
Erythromycin es 400 mg tablet0.25USD tablet
Apo-Erythro-S 250 mg Tablet0.22USD tablet
Apo-Erythro Base 250 mg Tablet0.19USD tablet
Erythrocin 250 mg filmtab0.16USD tablet
Novo-Rythro Ees 80 mg/ml Suspension0.15USD ml
Novo-Rythro Estolate 50 mg/ml Suspension0.13USD ml
Novo-Rythro Ees 40 mg/ml Suspension0.1USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)133-135 https://www.chemicalbook.com/ChemicalProductProperty_US_CB8300078.aspx
boiling point (°C)719.69°C (rough estimate)https://www.chemicalbook.com/ChemicalProductProperty_US_CB8300078.aspx
water solubilitySoluble in water at 2mg/mlhttps://www.chemicalbook.com/ChemicalProductProperty_US_CB8300078.aspx
logP2.6http://www.t3db.ca/toxins/T3D4764
logS-3.2http://www.t3db.ca/toxins/T3D4764
pKa8.88 (at 25 °C)https://www.chemicalbook.com/ChemicalProductProperty_US_CB8300078.aspx
Predicted Properties
PropertyValueSource
Water Solubility0.459 mg/mLALOGPS
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 Area193.91 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity186.04 m3·mol-1ChemAxon
Polarizability78.21 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5114
Blood Brain Barrier-0.9889
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8098
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IINon-inhibitor0.5963
Renal organic cation transporterNon-inhibitor0.9222
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9225
CYP450 3A4 substrateSubstrate0.6528
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9074
CYP450 3A4 inhibitorNon-inhibitor0.5744
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9391
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9335
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2296 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9902
hERG inhibition (predictor II)Non-inhibitor0.8956
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-Ion Trap , PositiveLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-Hybrid FT , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a7i-0900070700-45f1a3bf3aac26069507
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900020000-c282d6a703a3a812c91a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-b11e26802dca28ea88f0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-5ea1e94063a49c0d6ddb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0000090000-f0fcdc5ed4d00170f2a3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0200000900-439b7d31b57ea93dff40
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a59-4900000000-1cb488a53f50cba638cf
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-9700000000-239fd7095409362c75bc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-9000000000-37757a9a6c61ec2bac1b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-9000000000-2d04ae69b21d82ee0763
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-9000000000-2d04ae69b21d82ee0763
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-053r-0500000900-20a1c46dfdef404c9d3e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a59-5900000000-c7e9166d7e79e23023a5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-053r-9800000000-07e4c66bcd0be93f7c09
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-9200000000-553fb27002eceacb9270
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-9000000000-9725c29b26f7cbbef576
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-9000000000-2d04ae69b21d82ee0763
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0000090100-c815622b0bac716ba224
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0000020900-78ac24c4a3447cf2cb78
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0000090400-0c8362975e5b8d5441bb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0200090000-b4daabb8616be713f34c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900020000-595b522fe60bb668626a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0041090000-e9aadb2dff7c545dfce4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0020092000-6a2a3f6a74deed47dd72
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-056r-0070390000-4f9cd4f2a3b1e945ccfa
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fw9-0004960000-669f9bf82a144b4b5cdb

Taxonomy

Description
This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminoglycosides
Alternative Parents
Macrolides and analogues / O-glycosyl compounds / Monosaccharides / Oxanes / Tertiary alcohols / 1,2-aminoalcohols / Trialkylamines / Lactones / Cyclic ketones / Carboxylic acid esters
show 10 more
Substituents
Aminoglycoside core / Macrolide / Glycosyl compound / O-glycosyl compound / Oxane / Monosaccharide / Tertiary alcohol / 1,2-aminoalcohol / Amino acid or derivatives / Carboxylic acid ester
show 23 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
erythromycin (CHEBI:42355) / Macrolides and lactone polyketides, Macrolides (C01912) / Macrolides and lactone polyketides (LMPK04000006)

Targets

1. 23S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Inhibitor
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: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:11677599]
  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:11698379]
  4. Douthwaite S, Aagaard C: Erythromycin binding is reduced in ribosomes with conformational alterations in the 23 S rRNA peptidyl transferase loop. J Mol Biol. 1993 Aug 5;232(3):725-31. [PubMed:7689111]
  5. Wahab HA, Yam WK, Samian MR, Najimudin N: Refinement of a low-resolution crystal structure to better understand erythromycin interactions on large ribosomal subunit. J Biomol Struct Dyn. 2008 Aug;26(1):131-46. [PubMed:18533733]
  6. FDA label, erythromycin [File]
Details
2. Motilin receptor
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Agonist
General Function
Growth hormone-releasing hormone receptor activity
Specific Function
Receptor for motilin.
Gene Name
MLNR
Uniprot ID
O43193
Uniprot Name
Motilin receptor
Molecular Weight
45343.725 Da
References
  1. Peeters T, Matthijs G, Depoortere I, Cachet T, Hoogmartens J, Vantrappen G: Erythromycin is a motilin receptor agonist. Am J Physiol. 1989 Sep;257(3 Pt 1):G470-4. [PubMed:2782416]
  2. Deloose E, Vos R, Janssen P, Van den Bergh O, Van Oudenhove L, Depoortere I, Tack J: The motilin receptor agonist erythromycin stimulates hunger and food intake through a cholinergic pathway. Am J Clin Nutr. 2016 Mar;103(3):730-7. doi: 10.3945/ajcn.115.113456. Epub 2016 Jan 27. [PubMed:26817505]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
The majority of references suggest that this drug is a weak inhibitor of the HERG potassium channel.
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
Molecular Weight
126653.52 Da
References
  1. Du LP, Tsai KC, Li MY, You QD, Xia L: The pharmacophore hypotheses of I(Kr) potassium channel blockers: novel class III antiarrhythmic agents. Bioorg Med Chem Lett. 2004 Sep 20;14(18):4771-7. [PubMed:15324906]
  2. Stanat SJ, Carlton CG, Crumb WJ Jr, Agrawal KC, Clarkson CW: Characterization of the inhibitory effects of erythromycin and clarithromycin on the HERG potassium channel. Mol Cell Biochem. 2003 Dec;254(1-2):1-7. [PubMed:14674677]
  3. Crumb WJ Jr: Allosteric effects of erythromycin pretreatment on thioridazine block of hERG potassium channels. Br J Pharmacol. 2014 Apr;171(7):1668-75. doi: 10.1111/bph.12575. [PubMed:24417241]
4. Bacterial 50S Ribosomal Subunit
Kind
Protein group
Organism
Not Available
Pharmacological action
Yes
This is a broad protein group that is comprised of the 50S subunit of many bacterial organisms.
References
  1. Erythromycin FDA label [File]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Orlando R, Piccoli P, De Martin S, Padrini R, Palatini P: Effect of the CYP3A4 inhibitor erythromycin on the pharmacokinetics of lignocaine and its pharmacologically active metabolites in subjects with normal and impaired liver function. Br J Clin Pharmacol. 2003 Jan;55(1):86-93. [PubMed:12534644]
  2. Kenworthy KE, Bloomer JC, Clarke SE, Houston JB: CYP3A4 drug interactions: correlation of 10 in vitro probe substrates. Br J Clin Pharmacol. 1999 Nov;48(5):716-27. [PubMed:10594474]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  4. Erythromycin monograph [File]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Torimoto N, Ishii I, Toyama K, Hata M, Tanaka K, Shimomura H, Nakamura H, Ariyoshi N, Ohmori S, Kitada M: Helices F-G are important for the substrate specificities of CYP3A7. Drug Metab Dispos. 2007 Mar;35(3):484-92. doi: 10.1124/dmd.106.011304. Epub 2006 Dec 18. [PubMed:17178770]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  3. FDA label Erythromycin [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. McConn DJ 2nd, Lin YS, Allen K, Kunze KL, Thummel KE: Differences in the inhibition of cytochromes P450 3A4 and 3A5 by metabolite-inhibitor complex-forming drugs. Drug Metab Dispos. 2004 Oct;32(10):1083-91. doi: 10.1124/dmd.32.10.. [PubMed:15377640]
  2. Lolodi O, Wang YM, Wright WC, Chen T: Differential Regulation of CYP3A4 and CYP3A5 and its Implication in Drug Discovery. Curr Drug Metab. 2017;18(12):1095-1105. doi: 10.2174/1389200218666170531112038. [PubMed:28558634]
  3. Flockhart Table - Indiana University [Link]
  4. Erythromycin FDA label [File]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Kalliokoski A, Niemi M: Impact of OATP transporters on pharmacokinetics. Br J Pharmacol. 2009 Oct;158(3):693-705. doi: 10.1111/j.1476-5381.2009.00430.x. Epub 2009 Sep 25. [PubMed:19785645]
  2. Konig J: Uptake transporters of the human OATP family: molecular characteristics, substrates, their role in drug-drug interactions, and functional consequences of polymorphisms. Handb Exp Pharmacol. 2011;(201):1-28. doi: 10.1007/978-3-642-14541-4_1. [PubMed:21103967]
  3. Franke RM, Baker SD, Mathijssen RH, Schuetz EG, Sparreboom A: Influence of solute carriers on the pharmacokinetics of CYP3A4 probes. Clin Pharmacol Ther. 2008 Dec;84(6):704-9. doi: 10.1038/clpt.2008.94. Epub 2008 May 28. [PubMed:18509328]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]
  2. Kock K, Ferslew BC, Netterberg I, Yang K, Urban TJ, Swaan PW, Stewart PW, Brouwer KL: Risk factors for development of cholestatic drug-induced liver injury: inhibition of hepatic basolateral bile acid transporters multidrug resistance-associated proteins 3 and 4. Drug Metab Dispos. 2014 Apr;42(4):665-74. doi: 10.1124/dmd.113.054304. Epub 2013 Oct 23. [PubMed:24154606]
  3. Padda MS, Sanchez M, Akhtar AJ, Boyer JL: Drug-induced cholestasis. Hepatology. 2011 Apr;53(4):1377-87. doi: 10.1002/hep.24229. [PubMed:21480339]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. 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:9822896]
  2. Schwarz UI, Gramatte T, Krappweis J, Oertel R, Kirch W: P-glycoprotein inhibitor erythromycin increases oral bioavailability of talinolol in humans. Int J Clin Pharmacol Ther. 2000 Apr;38(4):161-7. [PubMed:10783825]
  3. 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:10817732]
  4. Vadlapatla RK, Vadlapudi AD, Kwatra D, Pal D, Mitra AK: Differential effect of P-gp and MRP2 on cellular translocation of gemifloxacin. Int J Pharm. 2011 Nov 25;420(1):26-33. doi: 10.1016/j.ijpharm.2011.08.009. Epub 2011 Aug 16. [PubMed:21864659]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. 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:15286055]
  2. Kalliokoski A, Niemi M: Impact of OATP transporters on pharmacokinetics. Br J Pharmacol. 2009 Oct;158(3):693-705. doi: 10.1111/j.1476-5381.2009.00430.x. Epub 2009 Sep 25. [PubMed:19785645]
  3. Konig J: Uptake transporters of the human OATP family: molecular characteristics, substrates, their role in drug-drug interactions, and functional consequences of polymorphisms. Handb Exp Pharmacol. 2011;(201):1-28. doi: 10.1007/978-3-642-14541-4_1. [PubMed:21103967]
  4. Franke RM, Baker SD, Mathijssen RH, Schuetz EG, Sparreboom A: Influence of solute carriers on the pharmacokinetics of CYP3A4 probes. Clin Pharmacol Ther. 2008 Dec;84(6):704-9. doi: 10.1038/clpt.2008.94. Epub 2008 May 28. [PubMed:18509328]
  5. Lancaster CS, Bruun GH, Peer CJ, Mikkelsen TS, Corydon TJ, Gibson AA, Hu S, Orwick SJ, Mathijssen RH, Figg WD, Baker SD, Sparreboom A: OATP1B1 polymorphism as a determinant of erythromycin disposition. Clin Pharmacol Ther. 2012 Nov;92(5):642-50. doi: 10.1038/clpt.2012.106. Epub 2012 Sep 19. [PubMed:22990751]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Franke RM, Lancaster CS, Peer CJ, Gibson AA, Kosloske AM, Orwick SJ, Mathijssen RH, Figg WD, Baker SD, Sparreboom A: Effect of ABCC2 (MRP2) transport function on erythromycin metabolism. Clin Pharmacol Ther. 2011 May;89(5):693-701. doi: 10.1038/clpt.2011.25. Epub 2011 Mar 30. [PubMed:21451505]
  2. Ogasawara K, Chitnis SD, Gohh RY, Christians U, Akhlaghi F: Multidrug resistance-associated protein 2 (MRP2/ABCC2) haplotypes significantly affect the pharmacokinetics of tacrolimus in kidney transplant recipients. Clin Pharmacokinet. 2013 Sep;52(9):751-62. doi: 10.1007/s40262-013-0069-2. [PubMed:23633119]
  3. Vadlapatla RK, Vadlapudi AD, Kwatra D, Pal D, Mitra AK: Differential effect of P-gp and MRP2 on cellular translocation of gemifloxacin. Int J Pharm. 2011 Nov 25;420(1):26-33. doi: 10.1016/j.ijpharm.2011.08.009. Epub 2011 Aug 16. [PubMed:21864659]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Franke RM, Baker SD, Mathijssen RH, Schuetz EG, Sparreboom A: Influence of solute carriers on the pharmacokinetics of CYP3A4 probes. Clin Pharmacol Ther. 2008 Dec;84(6):704-9. doi: 10.1038/clpt.2008.94. Epub 2008 May 28. [PubMed:18509328]
  2. Lan T, Rao A, Haywood J, Davis CB, Han C, Garver E, Dawson PA: Interaction of macrolide antibiotics with intestinally expressed human and rat organic anion-transporting polypeptides. Drug Metab Dispos. 2009 Dec;37(12):2375-82. doi: 10.1124/dmd.109.028522. Epub 2009 Sep 9. [PubMed:19741038]

Drug created on June 13, 2005 07:24 / Updated on February 16, 2019 05:56