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Details

Stereochemistry ABSOLUTE
Molecular Formula C37H67NO13.C2H2O4.2H2O
Molecular Weight 859.9922
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERYTHROMYCIN OXALATE DIHYDRATE

SMILES

O.O.OC(=O)C(O)=O.[H][C@@]1(C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)O[C@H]2[C@H](C)[C@@H](O[C@]3([H])O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]2C

InChI

InChIKey=BSTFTBLRGBLRTI-PHMXLGLWSA-N
InChI=1S/C37H67NO13.C2H2O4.2H2O/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;3-1(4)2(5)6;;/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;(H,3,4)(H,5,6);2*1H2/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-;;;/m1.../s1

HIDE SMILES / InChI

Molecular Formula C37H67NO13
Molecular Weight 733.9268
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C2H2O4
Molecular Weight 90.0349
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68015643

Erythromycin ethylsuccinate (E.E.S.®, ERY-PED®) is an ester of erythromycin base and succinic acid. It is suitable for oral administration. Erythromycin is a macrolide antibiotic, produced by Saccharopolyspora erythraea (formerly Streptomyces erythraeus). It acts primarily as a bacteriostatic agent. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins. Erythromycin does not affect nucleic acid synthesis.

CNS Activity

Curator's Comment: Information about erythromycin ethylsuccinate is unavailable.

Originator

Curator's Comment: Information about erythromycin ethylsuccinate is unavailable.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Erythromycin

Approved Use

Erythromycin is indicated in the treatment of respiratory tract infections due to Mycoplasma pneumoniae; skin and skin structure infections of mild to moderate severity caused by Streptococcus pyogenes or Staphylococcus aureus; listeriosis caused by Listeria monocytogenes; diphtheria due to Corynebacterium diphtheriae infection, as an adjunct to antitoxin, to prevent establishment of carriers and to eradicate the organism in carriers; erythrasma due to Corynebacterium minutissimum infection.

Launch Date

7.9660802E10
Curative
Erythromycin

Approved Use

Erythromycin is indicated in the treatment of respiratory tract infections due to Mycoplasma pneumoniae; skin and skin structure infections of mild to moderate severity caused by Streptococcus pyogenes or Staphylococcus aureus; listeriosis caused by Listeria monocytogenes; diphtheria due to Corynebacterium diphtheriae infection, as an adjunct to antitoxin, to prevent establishment of carriers and to eradicate the organism in carriers; erythrasma due to Corynebacterium minutissimum infection.

Launch Date

7.9660802E10
Curative
Erythromycin

Approved Use

Erythromycin is indicated in the treatment of respiratory tract infections due to Mycoplasma pneumoniae; skin and skin structure infections of mild to moderate severity caused by Streptococcus pyogenes or Staphylococcus aureus; listeriosis caused by Listeria monocytogenes; diphtheria due to Corynebacterium diphtheriae infection, as an adjunct to antitoxin, to prevent establishment of carriers and to eradicate the organism in carriers; erythrasma due to Corynebacterium minutissimum infection.

Launch Date

7.9660802E10
Curative
Erythromycin

Approved Use

Erythromycin is indicated in the treatment of respiratory tract infections due to Mycoplasma pneumoniae; skin and skin structure infections of mild to moderate severity caused by Streptococcus pyogenes or Staphylococcus aureus; listeriosis caused by Listeria monocytogenes; diphtheria due to Corynebacterium diphtheriae infection, as an adjunct to antitoxin, to prevent establishment of carriers and to eradicate the organism in carriers; erythrasma due to Corynebacterium minutissimum infection.

Launch Date

7.9660802E10
Curative
Erythromycin

Approved Use

Erythromycin is indicated in the treatment of respiratory tract infections due to Mycoplasma pneumoniae; skin and skin structure infections of mild to moderate severity caused by Streptococcus pyogenes or Staphylococcus aureus; listeriosis caused by Listeria monocytogenes; diphtheria due to Corynebacterium diphtheriae infection, as an adjunct to antitoxin, to prevent establishment of carriers and to eradicate the organism in carriers; erythrasma due to Corynebacterium minutissimum infection.

Launch Date

7.9660802E10
Curative
Davercin

Approved Use

For the topical treatment of acne vulgaris
Curative
Davercin

Approved Use

For the topical treatment of pneumonia
Curative
Davercin

Approved Use

Indicated for the treatment of bacterial endocarditis
Curative
Davercin

Approved Use

Unknown
Curative
E.E.S.

Approved Use

E.E.S. is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the diseases listed below: 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). Lower-respiratory tract infections of mild to moderate severity caused by Streptococcus pneumonia or Streptococcus pyogenes. Listeriosis caused by Listeria monocytogenes. 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. Respiratory tract infections due to Mycoplasma pneumoniae. Skin and skin structure infections of mild to moderate severity caused by Streptococcus pyogenes or Staphylococcus aureus (resistant staphylococci may emerge during treatment). Diphtheria: Infections due to Corynebacterium diphtheria , as an adjunct to antitoxin, to prevent establishment of carriers and to eradicate the organism in carriers. Erythrasma: In the treatment of infections due to Corynebacterium minutissimum. Intestinal amebiasis caused by Entamoeba histolytica (oral erythromycins only). Extraenteric amebiasis requires treatment with other agents. 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. 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. Erythromycins are indicated for the treatment of the following infections caused by 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. When tetracyclines are contraindicated or not tolerated, erythromycin is indicated for the treatment of nongonococcal urethritis caused by Ureaplasma urealyticum. 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.

Launch Date

-1.49990408E11
Curative
E.E.S.

Approved Use

E.E.S. is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the diseases listed below: 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). Lower-respiratory tract infections of mild to moderate severity caused by Streptococcus pneumonia or Streptococcus pyogenes. Listeriosis caused by Listeria monocytogenes. 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. Respiratory tract infections due to Mycoplasma pneumoniae. Skin and skin structure infections of mild to moderate severity caused by Streptococcus pyogenes or Staphylococcus aureus (resistant staphylococci may emerge during treatment). Diphtheria: Infections due to Corynebacterium diphtheria , as an adjunct to antitoxin, to prevent establishment of carriers and to eradicate the organism in carriers. Erythrasma: In the treatment of infections due to Corynebacterium minutissimum. Intestinal amebiasis caused by Entamoeba histolytica (oral erythromycins only). Extraenteric amebiasis requires treatment with other agents. 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. 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. Erythromycins are indicated for the treatment of the following infections caused by 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. When tetracyclines are contraindicated or not tolerated, erythromycin is indicated for the treatment of nongonococcal urethritis caused by Ureaplasma urealyticum. 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.

Launch Date

-1.49990408E11
Curative
E.E.S

Approved Use

E.E.S. is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the diseases listed below: 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). Lower-respiratory tract infections of mild to moderate severity caused by Streptococcus pneumonia or Streptococcus pyogenes. Listeriosis caused by Listeria monocytogenes. 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. Respiratory tract infections due to Mycoplasma pneumoniae. Skin and skin structure infections of mild to moderate severity caused by Streptococcus pyogenes or Staphylococcus aureus (resistant staphylococci may emerge during treatment). Diphtheria: Infections due to Corynebacterium diphtheria , as an adjunct to antitoxin, to prevent establishment of carriers and to eradicate the organism in carriers. Erythrasma: In the treatment of infections due to Corynebacterium minutissimum. Intestinal amebiasis caused by Entamoeba histolytica (oral erythromycins only). Extraenteric amebiasis requires treatment with other agents. 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. 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. Erythromycins are indicated for the treatment of the following infections caused by 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. When tetracyclines are contraindicated or not tolerated, erythromycin is indicated for the treatment of nongonococcal urethritis caused by Ureaplasma urealyticum. 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.

Launch Date

-1.49990408E11
Curative
E.E.S.

Approved Use

E.E.S. is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the diseases listed below: 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). Lower-respiratory tract infections of mild to moderate severity caused by Streptococcus pneumonia or Streptococcus pyogenes. Listeriosis caused by Listeria monocytogenes. 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. Respiratory tract infections due to Mycoplasma pneumoniae. Skin and skin structure infections of mild to moderate severity caused by Streptococcus pyogenes or Staphylococcus aureus (resistant staphylococci may emerge during treatment). Diphtheria: Infections due to Corynebacterium diphtheria , as an adjunct to antitoxin, to prevent establishment of carriers and to eradicate the organism in carriers. Erythrasma: In the treatment of infections due to Corynebacterium minutissimum. Intestinal amebiasis caused by Entamoeba histolytica (oral erythromycins only). Extraenteric amebiasis requires treatment with other agents. 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. 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. Erythromycins are indicated for the treatment of the following infections caused by 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. When tetracyclines are contraindicated or not tolerated, erythromycin is indicated for the treatment of nongonococcal urethritis caused by Ureaplasma urealyticum. 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.

Launch Date

-1.50076801E11
Curative
E.E.S.

Approved Use

E.E.S. is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the diseases listed below: 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). Lower-respiratory tract infections of mild to moderate severity caused by Streptococcus pneumonia or Streptococcus pyogenes. Listeriosis caused by Listeria monocytogenes. 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. Respiratory tract infections due to Mycoplasma pneumoniae. Skin and skin structure infections of mild to moderate severity caused by Streptococcus pyogenes or Staphylococcus aureus (resistant staphylococci may emerge during treatment). Diphtheria: Infections due to Corynebacterium diphtheria , as an adjunct to antitoxin, to prevent establishment of carriers and to eradicate the organism in carriers. Erythrasma: In the treatment of infections due to Corynebacterium minutissimum. Intestinal amebiasis caused by Entamoeba histolytica (oral erythromycins only). Extraenteric amebiasis requires treatment with other agents. 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. 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. Erythromycins are indicated for the treatment of the following infections caused by 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. When tetracyclines are contraindicated or not tolerated, erythromycin is indicated for the treatment of nongonococcal urethritis caused by Ureaplasma urealyticum. 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.

Launch Date

-1.50076801E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.18 μg/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERYTHROMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2.44 μg/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERYTHROMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.62 μg/mL
250 mg 4 times / day multiple, oral
dose: 250 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ERYTHROMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.99 μg/mL
250 mg 4 times / day multiple, oral
dose: 250 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ERYTHROMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1161.5 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERYTHROMYCIN unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1386.1 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERYTHROMYCIN unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3.1 μg × h/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERYTHROMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.1 μg × h/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERYTHROMYCIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3544.7 ng × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERYTHROMYCIN unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4096.7 ng × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERYTHROMYCIN unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.48 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERYTHROMYCIN unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
5.31 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ERYTHROMYCIN unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
5 g 1 times / day single, oral
Studied dose
Dose: 5 g, 1 times / day
Route: oral
Route: single
Dose: 5 g, 1 times / day
Sources:
healthy, 12 years
n = 1
Health Status: healthy
Age Group: 12 years
Sex: F
Population Size: 1
Sources:
Other AEs: Pancreatitis...
Other AEs:
Pancreatitis
Sources:
5.3 g 1 times / day single, oral
Studied dose
Dose: 5.3 g, 1 times / day
Route: oral
Route: single
Dose: 5.3 g, 1 times / day
Sources:
healthy, 15 years
n = 1
Health Status: healthy
Age Group: 15 years
Sex: F
Population Size: 1
Sources:
Other AEs: Pancreatitis...
Other AEs:
Pancreatitis
Sources:
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
unhealthy, mean age 30 years
n = 35
Health Status: unhealthy
Condition: maxillary sinusitis
Age Group: mean age 30 years
Sex: M+F
Population Size: 35
Sources:
Disc. AE: Vomiting...
AEs leading to
discontinuation/dose reduction:
Vomiting (2.8%)
Sources:
500 mg 3 times / day multiple, oral
Recommended
Dose: 500 mg, 3 times / day
Route: oral
Route: multiple
Dose: 500 mg, 3 times / day
Sources:
unhealthy, mean age 30 years
n = 41
Health Status: unhealthy
Condition: maxillary sinusitis
Age Group: mean age 30 years
Sex: M+F
Population Size: 41
Sources:
Disc. AE: Nausea, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Nausea (14.6%)
Abdominal pain (4.9%)
Sources:
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
unhealthy, mean age 44 years
n = 120
Health Status: unhealthy
Condition: streptococcal pharyngitis
Age Group: mean age 44 years
Sex: M+F
Population Size: 120
Sources:
Disc. AE: Epigastralgia, Nausea...
AEs leading to
discontinuation/dose reduction:
Epigastralgia (grade 2-3, 2.5%)
Nausea (grade 3, 3.3%)
Vomiting (grade 2, 0.8%)
Sources:
100 mg single, intravenous
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
unhealthy
n = 9
Health Status: unhealthy
Condition: Parkinson's Disease
Population Size: 9
Sources:
Other AEs: Akathisia, Diarrhea...
Other AEs:
Akathisia (below serious, 1 patient)
Diarrhea (below serious, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Pancreatitis
5 g 1 times / day single, oral
Studied dose
Dose: 5 g, 1 times / day
Route: oral
Route: single
Dose: 5 g, 1 times / day
Sources:
healthy, 12 years
n = 1
Health Status: healthy
Age Group: 12 years
Sex: F
Population Size: 1
Sources:
Pancreatitis
5.3 g 1 times / day single, oral
Studied dose
Dose: 5.3 g, 1 times / day
Route: oral
Route: single
Dose: 5.3 g, 1 times / day
Sources:
healthy, 15 years
n = 1
Health Status: healthy
Age Group: 15 years
Sex: F
Population Size: 1
Sources:
Vomiting 2.8%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
unhealthy, mean age 30 years
n = 35
Health Status: unhealthy
Condition: maxillary sinusitis
Age Group: mean age 30 years
Sex: M+F
Population Size: 35
Sources:
Nausea 14.6%
Disc. AE
500 mg 3 times / day multiple, oral
Recommended
Dose: 500 mg, 3 times / day
Route: oral
Route: multiple
Dose: 500 mg, 3 times / day
Sources:
unhealthy, mean age 30 years
n = 41
Health Status: unhealthy
Condition: maxillary sinusitis
Age Group: mean age 30 years
Sex: M+F
Population Size: 41
Sources:
Abdominal pain 4.9%
Disc. AE
500 mg 3 times / day multiple, oral
Recommended
Dose: 500 mg, 3 times / day
Route: oral
Route: multiple
Dose: 500 mg, 3 times / day
Sources:
unhealthy, mean age 30 years
n = 41
Health Status: unhealthy
Condition: maxillary sinusitis
Age Group: mean age 30 years
Sex: M+F
Population Size: 41
Sources:
Vomiting grade 2, 0.8%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
unhealthy, mean age 44 years
n = 120
Health Status: unhealthy
Condition: streptococcal pharyngitis
Age Group: mean age 44 years
Sex: M+F
Population Size: 120
Sources:
Epigastralgia grade 2-3, 2.5%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
unhealthy, mean age 44 years
n = 120
Health Status: unhealthy
Condition: streptococcal pharyngitis
Age Group: mean age 44 years
Sex: M+F
Population Size: 120
Sources:
Nausea grade 3, 3.3%
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
unhealthy, mean age 44 years
n = 120
Health Status: unhealthy
Condition: streptococcal pharyngitis
Age Group: mean age 44 years
Sex: M+F
Population Size: 120
Sources:
Akathisia below serious, 1 patient
100 mg single, intravenous
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
unhealthy
n = 9
Health Status: unhealthy
Condition: Parkinson's Disease
Population Size: 9
Sources:
Diarrhea below serious, 1 patient
100 mg single, intravenous
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
unhealthy
n = 9
Health Status: unhealthy
Condition: Parkinson's Disease
Population Size: 9
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
moderate [IC50 9.9 uM]
yes (co-administration study)
Comment: Erythromycin increased mean Cmax value of simvastatin 3.4 fold and AUC0-24 value 6.2 fold; coadministered erythromycin has been reported to increase AUCs of simvastatin, triazolam, and midazolam 6.2-, 3.6-, and 3.8-fold, respectively; A significant increase in colchicine plasma concentration is anticipated when co-administered with moderate CYP3A4 inhibitors such as erythromycin;
Page: 10.0
yes [IC50 217 uM]
yes [IC50 22.7 uM]
yes [IC50 34 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
likely (co-administration study)
Comment: Coadministration of erythromycin and a drug primarily metabolized by CYP3A may be associated with elevations in drug concentrations that could increase or prolong both the therapeutic and adverse effects of the concomitant drug
Page: 9.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
A C-13 relaxation study on erythromycin A cyclic 11,12-carbonate.
1978 May
Comparison of the mechanism of action of cyclic 11,12-erythromycin A carbonate and erythromycin A.
1980
Drug-induced gallbladder disease. Incidence, aetiology and management.
1992 Jan-Feb
[Bacteriostatic activity and killing curves of eight antibiotics against seven strains of penicillin G-resistant pneumococci].
1992 May
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Bioavailability and stability of erythromycin delayed release tablets.
2001 Dec
Massive venlafaxine overdose resulted in a false positive Abbott AxSYM urine immunoassay for phencyclidine.
2003
Mixed chimerism of erythro- and megakaryopoiesis following allogeneic bone marrow transplantation.
2003
Gamma-fluorinated analogues of glutamic acid and glutamine.
2003 Apr
[Postoperative ileus: part II (Clinical therapy)].
2003 Apr
Effects of amphotericin B and caspofungin on histamine expression.
2003 Aug
Effect of erythromycin on contractile response of uterine smooth muscle strips in non-pregnant rats.
2003 Jan-Feb
Stereoselective biosynthesis of chloroarylpropane diols by the basidiomycete Bjerkandera adusta.
2003 Jul
Modifications to the N-terminus but not the C-terminus of calcitonin gene-related peptide(8-37) produce antagonists with increased affinity.
2003 Jun 5
Systematic synthesis of Bis-THF ring cores in annonaceous acetogenins.
2003 May 1
Ratio of erythro and threo forms of beta-O-4 structures in tension wood lignin.
2003 Nov
Straightforward synthesis of sphinganines via a serine-derived Weinreb amide.
2004 Apr 30
Bitterness evaluation of medicines for pediatric use by a taste sensor.
2004 Aug
Delayed Gastric Emptying in Functional Dyspepsia.
2004 Aug
Evidence of significant contribution from CYP3A5 to hepatic drug metabolism.
2004 Dec
Local mechanisms underlying the regulatory effect of Kropanol on hemopoiesis during paradoxical sleep deprivation.
2004 Feb
Dicloxacillin and erythromycin at high concentrations increase ICAM-1 expression by endothelial cells: a possible factor in the pathogenesis of infusion phlebitis.
2004 Feb
[3 + 2] Cycloreversion of bicyclo[m.3.0]alkan-3-on-2-yl-1-oxonium ylides to alkenyloxyketenes. Stereospecific aspect.
2004 Feb 20
Cytochrome P450/NADPH-dependent formation of trans epoxides from trans-arachidonic acids.
2004 Feb 23
Validation of a [3H]astemizole binding assay in HEK293 cells expressing HERG K+ channels.
2004 Jul
Highly diastereoselective reductive coupling of 2-bromo-2,3,3,3-tetrafluoropropanamide with aldehydes promoted by triphenylphosphine-titanium(IV) isopropoxide. An efficient route to the synthesis of erythro-alpha-fluoro-alpha-(trifluoromethyl)-beta-hydroxy amides.
2004 Jul 23
[Usefulness of oral exfoliative cytology for the diagnosis of oral squamous dysplasia and carcinoma].
2004 Mar
Effect of particle size on mixing degree in dispensation.
2004 Mar
Effect of mixing method on the mixing degree during the preparation of triturations.
2004 Mar
Conformational study of a guaiacyl beta-O-4 lignin model compound by NMR. Examination of intramolecular hydrogen bonding interactions and conformational flexibility in solution.
2004 Mar
Mechanism of beta-silyl diacyl peroxide decomposition: a mild and stereoselective synthesis of beta-silyl esters.
2004 May 28
Anti-proliferative effects of lichen-derived lipoxygenase inhibitors on twelve human cancer cell lines of different tissue origin in vitro.
2004 Nov
Comparative pharmacodynamics and plasma concentrations of d-threo-methylphenidate hydrochloride after single doses of d-threo-methylphenidate hydrochloride and d,l-threo-methylphenidate hydrochloride in a double-blind, placebo-controlled, crossover laboratory school study in children with attention-deficit/hyperactivity disorder.
2004 Nov
Enantiomeric separation of racemic neolignans on chiralcel OD and determination of their absolute configuration with online circular dichroism.
2004 Oct
Effects of colchicine on the maximum biliary excretion of cholephilic compounds in rats.
2004 Sep
Initial (latent) polycythemia vera with thrombocytosis mimicking essential thrombocythemia.
2005
In vitro and in vivo activities of macrolide derivatives against Mycobacterium tuberculosis.
2005 Apr
Standardization of bone marrow features--does it work in hematopathology for histological discrimination of different disease patterns?
2005 Apr
Comparison of information on the pharmacokinetic interactions of Ca antagonists in the package inserts from three countries (Japan, USA and UK).
2005 Aug
On the CH...Cu agostic interaction: chiral copper(II) compounds with ephedrine and pseudoephedrine derivatives.
2005 Aug 14
Randomised controlled multiple treatment comparison to provide a cost-effectiveness rationale for the selection of antimicrobial therapy in acne.
2005 Jan
High volume bioassays to assess CYP3A4-mediated drug interactions: induction and inhibition in a single cell line.
2005 Jan
On-line identification of sugarcane (Saccharum officinarum L.) methoxyflavones by liquid chromatography-UV detection using post-column derivatization and liquid chromatography-mass spectrometry.
2005 Jul 29
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Desensitization of the human motilin receptor by motilides.
2005 Jun
Molecular recognition of sialic acid end groups by phenylboronates.
2005 Jun 20
[Biological effects of a natural alkyl-diacylglyceride preparation in rats with experimental cardioangiopathy].
2005 Mar-Apr
Cytotoxicity of neolignans identified in Saururus chinensis towards human cancer cell lines.
2005 May
Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]).
2005 May
The effect of erythromycin and fluvoxamine on the pharmacokinetics of intravenous lidocaine.
2005 May
Patents

Sample Use Guides

Initial dose - 30 mg/kg, then 15 mg/kg every 12 hours.
Route of Administration: Other
In Vitro Use Guide
At the concentration which stops polylysine synthesis by more than 80% (about 0.5 nM/100 pM of 70S ribosomes), the Erythromycin cyclocarbonate inhibited but slightly binding of phage f2 RNA to ribosomes.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:16:55 UTC 2023
Edited
by admin
on Fri Dec 15 15:16:55 UTC 2023
Record UNII
XSP28IFM29
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERYTHROMYCIN OXALATE DIHYDRATE
Common Name English
ERYTHROMYCIN, OXALATE (1:1), DIHYDRATE
Common Name English
Code System Code Type Description
FDA UNII
XSP28IFM29
Created by admin on Fri Dec 15 15:16:55 UTC 2023 , Edited by admin on Fri Dec 15 15:16:55 UTC 2023
PRIMARY
PUBCHEM
133082763
Created by admin on Fri Dec 15 15:16:55 UTC 2023 , Edited by admin on Fri Dec 15 15:16:55 UTC 2023
PRIMARY
CAS
14444-93-0
Created by admin on Fri Dec 15 15:16:55 UTC 2023 , Edited by admin on Fri Dec 15 15:16:55 UTC 2023
PRIMARY
CAS
14638-05-2
Created by admin on Fri Dec 15 15:16:55 UTC 2023 , Edited by admin on Fri Dec 15 15:16:55 UTC 2023
NON-SPECIFIC STOICHIOMETRY
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ACTIVE MOIETY