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Details

Stereochemistry ABSOLUTE
Molecular Formula C40H71NO14.C5H9NO3S
Molecular Weight 953.185
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERYTHROMYCIN STINOPRATE

SMILES

CC(=O)N[C@@H](CS)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]3OC(=O)CC)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=HXKNXCFNAJGZCM-PWOIWMLJSA-N
InChI=1S/C40H71NO14.C5H9NO3S/c1-15-27-40(11,48)33(44)22(5)30(43)20(3)18-38(9,47)35(55-37-32(53-28(42)16-2)26(41(12)13)17-21(4)50-37)23(6)31(24(7)36(46)52-27)54-29-19-39(10,49-14)34(45)25(8)51-29;1-3(7)6-4(2-10)5(8)9/h20-27,29,31-35,37,44-45,47-48H,15-19H2,1-14H3;4,10H,2H2,1H3,(H,6,7)(H,8,9)/t20-,21-,22+,23+,24-,25+,26+,27-,29+,31+,32-,33-,34+,35-,37+,38-,39-,40-;4-/m10/s1

HIDE SMILES / InChI

Molecular Formula C5H9NO3S
Molecular Weight 163.195
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C40H71NO14
Molecular Weight 789.99
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

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

1972
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

1972
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

1972
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

1972
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

1972
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

1965
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

1965
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

1965
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

1965
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

1965
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
[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
Torsade de pointes induced by metoclopramide in an elderly woman with preexisting complete left bundle branch block.
2001 Dec
The effects of grapefruit juice on the pharmacokinetics of erythromycin.
2001 Jan-Feb
Insertion of H2C=CHX (X = F, Cl, Br, O(i)Pr) into (tBu3SiO)3TaH2 and beta-X-Elimination from (tBu3SiO)3HTaCH2CH2X (X = OR): relevance to Ziegler-Natta copolymerizations.
2001 May 23
Synthesis of erythro and threo furanoid glycals from 1- and 2-phenylselenenyl-carbohydrate derivatives.
2001 Nov 8
Studies on macrolide antibiotics I. Synthesis and antibacterial activity of erythromycin A 9-O-substituted oxime ether derivatives against Mycobacterium avium complex.
2001 Sep
[Orotic acid as a metabolic agent].
2002
Antimicrobial-induced mania (antibiomania): a review of spontaneous reports.
2002 Feb
Stereoselective binding of 2-(4-biphenylyl)-3-substituted-3-hydroxypropionic acids on an immobilised human serum albumin chiral stationary phase.
2002 Feb 25
Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice.
2002 Jul
[Legionellosis in HIV-1 infected patients. 4 case reports].
2002 Mar 2
A density-functional study of the mechanism for the diastereoselective epoxidation of chiral allylic alcohols by the titanium peroxy complexes.
2002 Mar 8
Clinical evaluation of Double Strength Isotrexin versus Benzamycin in the topical treatment of mild to moderate acne vulgaris.
2002 Sep
QT prolongation and torsades de pointes associated with concurrent use of cisapride and erythromycin.
2002 Sep-Oct
[Postoperative ileus: part II (Clinical therapy)].
2003 Apr
Ipobscurines C and D: macrolactam-type indole alkaloids from the seeds of Ipomoea obscura.
2003 Apr
Effects of amphotericin B and caspofungin on histamine expression.
2003 Aug
Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria.
2003 Dec 1
Amifostine does not preferentially stimulate the growth of residual polyclonal progenitor cells in myelodysplastic syndromes.
2003 Jul
A highly chemoselective, diastereoselective, and regioselective epoxidation of chiral allylic alcohols with hydrogen peroxide, catalyzed by sandwich-type polyoxometalates: enhancement of reactivity and control of selectivity by the hydroxy group through metal-alcoholate bonding.
2003 Mar 7
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.
2003 Sep 1
Straightforward synthesis of sphinganines via a serine-derived Weinreb amide.
2004 Apr 30
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
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
Enantiomeric separation of racemic neolignans on chiralcel OD and determination of their absolute configuration with online circular dichroism.
2004 Oct
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
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 16:12:58 GMT 2023
Edited
by admin
on Fri Dec 15 16:12:58 GMT 2023
Record UNII
M6S6O570YO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERYTHROMYCIN STINOPRATE
INN   WHO-DD  
INN  
Official Name English
erythromycin stinoprate [INN]
Common Name English
ERYTHROMYCIN STINOPRATE [WHO-DD]
Common Name English
ERYSEC
Brand Name English
Code System Code Type Description
FDA UNII
M6S6O570YO
Created by admin on Fri Dec 15 16:12:59 GMT 2023 , Edited by admin on Fri Dec 15 16:12:59 GMT 2023
PRIMARY
EVMPD
SUB13706MIG
Created by admin on Fri Dec 15 16:12:59 GMT 2023 , Edited by admin on Fri Dec 15 16:12:59 GMT 2023
PRIMARY
PUBCHEM
71276
Created by admin on Fri Dec 15 16:12:59 GMT 2023 , Edited by admin on Fri Dec 15 16:12:59 GMT 2023
PRIMARY
CAS
84252-03-9
Created by admin on Fri Dec 15 16:12:59 GMT 2023 , Edited by admin on Fri Dec 15 16:12:59 GMT 2023
PRIMARY
INN
6020
Created by admin on Fri Dec 15 16:12:59 GMT 2023 , Edited by admin on Fri Dec 15 16:12:59 GMT 2023
PRIMARY
SMS_ID
100000078975
Created by admin on Fri Dec 15 16:12:59 GMT 2023 , Edited by admin on Fri Dec 15 16:12:59 GMT 2023
PRIMARY
NCI_THESAURUS
C174694
Created by admin on Fri Dec 15 16:12:59 GMT 2023 , Edited by admin on Fri Dec 15 16:12:59 GMT 2023
PRIMARY
RXCUI
236847
Created by admin on Fri Dec 15 16:12:59 GMT 2023 , Edited by admin on Fri Dec 15 16:12:59 GMT 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY