General
Preferred name
ERYTHROMYCIN
Synonyms
ERYTHROMYCIN STEARATE ()
erythromycin-A ()
E-Mycin ()
Erythromycin (thiocyanate) ()
Erythromycin thiocyanate ()
Sansac ()
T-Stat ()
Tiloryth ()
Oftalmolosa Cusi Eritromicina ()
E-Base ()
A/T/S ()
Eryc 125 ()
Eryacne 2 ()
Rommix 500 EC ()
Erythro-Statin ()
Ery-Tab ()
Paediathrocin ()
Wyamycin ()
Ilotycin ()
E-Glades ()
Isotrexin ()
Eryc Sprinkles ()
Bristamycin ()
Erythrocin ()
Kerymax ()
Robimycin ()
Erycette ()
Erythromycin estolate impurity, free erythromycin- ()
Erythra-Derm ()
R-P Mycin ()
C-Solve-2 ()
Erypar ()
Aknemycin Plus ()
ERYC ()
Eryderm ()
Erymax Sprinkle ()
Emgel ()
Retcin ()
Eritromicina ()
NSC-55929 ()
Eryacne 4 ()
Stiemycin ()
E-Solve 2 ()
Akne-Mycin ()
Zineryt ()
Erygel ()
Benzamycin ()
Staticin ()
J01FA01 ()
Pfizer-E ()
Gallimycin ()
Erythromycine ()
Erymax ()
PCE ()
Rommix 250 EC ()
Erythro 200 ()
Erythromycin ()
Abboticine ()
NSC-756747 ()
Erythrocin Acne Pack ()
Sk-erythromycin ()
Erythromycin octadecanoate (salt) ()
Erythrocin 500 ()
Erythrocin Stearate ()
Wyamycin S ()
Ethril 500 ()
Erythromycini stearas ()
Ethril 250 ()
Erythromycini lactobionas ()
Sterile erythromycin lactobionate ()
ERYTHROMYCIN LACTOBIONATE ()
Erythromycin Glucoheptonate ()
Ilotycin Gluceptate ()
ERYTHROMYCIN GLUCEPTATE ()
Erythromycin-13C-d3 ()
P&D ID
PD002345
CAS
114-07-8
643-22-1
82343-12-2
1334-39-0
1334-29-8
3847-29-8
23067-13-2
7704-67-8
2378755-50-9
Tags
available
natural product
drug
Approved by
FDA
First approval
1964
1982
Drug indication
Antibacterial
Bacterial infection
Drug Status
approved
vet_approved
investigational
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
HALF-LIFE 3.5 h [A174451] In patients with liver disease, the half-life has been shown to be significantly increased, however, this is of little clinical significance [F3322].
ROE In patients with normal hepatic function, erythromycin is concentrated in the liver and excreted in the bile [F3322]. Less than 5% of the orally administered dose of erythromycin is excreted in active form in the urine [F3322]. A large proportion of the absorbed drug remains unaccounted for and is presumably metabolized, probably in the liver [F3322].
PHARMACODYNAMICS Macrolides, such as erythromycin, stop bacterial growth by inhibiting protein synthesis and translation, treating bacterial infections [A174175]. Erythromycin does not exert effects on nucleic acid synthesis [FDA 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 [FDA 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 [FDA label].
MOA In order to replicate, bacteria require a specific process of protein synthesis, enabled by ribosomal proteins [A6505]. 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 [FDA label], [A14179]. This results in the control of various bacterial infections [A174193], [FDA label]. The strong affinity of macrolides, including erythromycin, for bacterial ribosomes, supports their broad‐spectrum antibacterial activities [A174193]. 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 [FDA label].
METABOLISM Hepatic first-pass metabolism contributes significantly to the total metabolism of erythromycin after oral dosing [A174457]. 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 [F3322]. Erythromycin is partially metabolized by CYP3A enzymes, which results in numerous drug interactions [FDA 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 [A174448].
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 [F3322]. Erythromycin is well known for its highly variable bioavailability (18-45%) [A174451] after oral ingestion and its susceptibility to be degraded under acidic conditions [A174448].
PHARMACODYNAMICS Macrolides, such as erythromycin, stop bacterial growth by inhibiting protein synthesis and translation, treating bacterial infections [A174175]. Erythromycin does not exert effects on nucleic acid synthesis [FDA 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 [FDA 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 [FDA label].; ;
MOA In order to replicate, bacteria require a specific process of protein synthesis, enabled by ribosomal proteins [A6505]. 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 [FDA label], [A14179]. This results in the control of various bacterial infections [A174193], [FDA label]. The strong affinity of macrolides, including erythromycin, for bacterial ribosomes, supports their broad‐spectrum antibacterial activities [A174193]. ; ; 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 [FDA label].
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 [FDA label].; ; ; **Hepatotoxicity**:; ; Erythromycin can cause hepatic dysfunction, cholestatic jaundice, and abnormal liver transaminases, particularly when _erythromycin estolate_ is administered [F3343].; ; **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 [FDA 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 [FDA label]. It is important to note that _erythromycin estolate_ is contraindicated in pregnancy [F3343].; ; **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 [FDA label].; ; **Nursing Mothers**: Erythromycin appears in breast milk at levels which are approximately 50% of the plasma concentration [F3322]. Caution should be observed when erythromycin is given to a nursing woman [FDA label].
METABOLISM Hepatic first-pass metabolism contributes significantly to the total metabolism of erythromycin after oral dosing [A174457]. 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 [F3322]. Erythromycin is partially metabolized by CYP3A enzymes, which results in numerous drug interactions [FDA 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 [A174448].
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 [F3322].; ; Erythromycin is well known for its highly variable bioavailability (18-45%) [A174451] after oral ingestion and its susceptibility to be degraded under acidic conditions [A174448].
HALF-LIFE 3.5 h [A174451] ; ; In patients with liver disease, the half-life has been shown to be significantly increased, however, this is of little clinical significance [F3322].
DESCRIPTION Erythromycin is a macrolide antibacterial produced by Streptomyces erythreus. (GtoPdb)
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 [FDA label]. **Hepatotoxicity**: Erythromycin can cause hepatic dysfunction, cholestatic jaundice, and abnormal liver transaminases, particularly when _erythromycin estolate_ is administered [F3343]. **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 [FDA 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 [FDA label]. It is important to note that _erythromycin estolate_ is contraindicated in pregnancy [F3343]. **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 [FDA label]. **Nursing Mothers**: Erythromycin appears in breast milk at levels which are approximately 50% of the plasma concentration [F3322]. Caution should be observed when erythromycin is given to a nursing woman [FDA label].
ROE In patients with normal hepatic function, erythromycin is concentrated in the liver and excreted in the bile [F3322]. Less than 5% of the orally administered dose of erythromycin is excreted in active form in the urine [F3322]. ; ; A large proportion of the absorbed drug remains unaccounted for and is presumably metabolized, probably in the liver [F3322].
Cell lines
0
Organisms
9
Compound Sets
27
Cayman Chemical Bioactives
16486
17189
25310
ChEMBL Approved Drugs
CHEMBL1200510
CHEMBL532
CHEMBL1200506
CHEMBL3545060
ChEMBL Drugs
CHEMBL1200510
CHEMBL532
CHEMBL1200506
CHEMBL3545060
Concise Guide to Pharmacology 2017/18
1456
Concise Guide to Pharmacology 2019/20
1456
Concise Guide to Pharmacology 2021/22
1456
Concise Guide to Pharmacology 2023/24
1456
Drug Repurposing Hub
DrugBank
DB00199
DrugBank Approved Drugs
DB00199
DrugCentral
1048
DrugCentral Approved Drugs
1048
DrugMAP
DM4K7GQ
DrugMAP Approved Drugs
DM4K7GQ
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS100785
Guide to Pharmacology
1456
MedChem Express Bioactive Compound Library
HY-B0220
HY-B0220D
NCATS Inxight Approved Drugs
63937KV33D
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Pandemic Response Box
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
erythromycin-thiocyanate
TargetMol Bioactive Compound Library
T1032
The Spectrum Collection
External IDs
130
Properties
(calculated by RDKit )
Molecular Weight
733.46
Hydrogen Bond Acceptors
14
Hydrogen Bond Donors
5
Rotatable Bonds
7
Ring Count
3
Aromatic Ring Count
0
cLogP
1.79
TPSA
193.91
Fraction CSP3
0.95
Chiral centers
18.0
Largest ring
14.0
QED
0.24
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Microbiology&virology
Anti-infection
Cell Cycle/DNA Damage
Target
23S rRNA
50S ribosome
MLNR
antibiotic
Bacterial
DNA/RNA Synthesis
Antibiotics,Bacterial
Member status
member
MOA
Motilin Receptor Agonists
NF-kappaB (NFKB) Activation Inhibitors
NFkB pathway inhibitor
Indication
listeria, respiratory tract infections, skin infections, syphilis, amebiasis, pelvic inflammatory disease, chlamydia, diphtheria, erythrasma
Therapeutic Class
Antibiotics
Source data