ERYTHROMYCIN THIOCYANATE

First approved in 1952

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C37H67NO13.CHNS
Molecular Weight	793.017
Optical Activity	UNSPECIFIED
Defined Stereocenters	18 / 18
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

SC#N.[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=WVRRTEYLDPNZHR-YZPBMOCRSA-N

InChI=1S/C37H67NO13.CHNS/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;2-1-3/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;3H/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	CHNS
Molecular Weight	59.09
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.przychodnia.pl/el/leki.php3?lek=628http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/061621s039lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050207s071lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/061621s039lbl.pdf	Binding Agent 1064	14.0 nM [Kd]
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7023159	Inhibitor 8297
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050207s071lbl.pdf	Binding Agent 1064	14.0 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Diphtheria 40 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/061621s039lbl.pdf	Curative	Approved 8429	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
Erythrasma 26 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/061621s039lbl.pdf	Curative	Approved 8429	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
Listeriosis 26 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/061621s039lbl.pdf	Curative	Approved 8429	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
Respiratory tract infections 85 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/061621s039lbl.pdf	Curative	Approved 8429	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
Skin and skin structure infections 80 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/061621s039lbl.pdf	Curative	Approved 8429	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
Acne 98 Sources: https://www.doz.pl/leki/p5178-Davercin_zel_plyn	Curative	Approved 8429	Davercin Approved Use For the topical treatment of acne vulgaris
Pneumonia 90 Sources: https://www.doz.pl/leki/p2615-Davercin_tabletki	Curative	Approved 8429	Davercin Approved Use For the topical treatment of pneumonia
Bacterial endocarditis 30 Sources: http://www.przychodnia.pl/el/leki.php3?lek=628	Curative	Approved 8429	Davercin Approved Use Indicated for the treatment of bacterial endocarditis
Staphylococcal dermatitis 26 Sources: https://www.doz.pl/leki/p2615-Davercin_tabletki	Curative	Approved 8429	Davercin Approved Use Unknown
Diphtheria 40 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050207s071lbl.pdf	Curative	Approved 8429	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
Skin and skin structure infections 80 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050207s071lbl.pdf	Curative	Approved 8429	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
Respiratory tract infections 85 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050207s071lbl.pdf	Curative	Approved 8429	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
Listeriosis 26 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050207s071lbl.pdf	Curative	Approved 8429	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
Erythrasma 26 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050207s071lbl.pdf	Curative	Approved 8429	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

C_max

Value	Dose	Analyte	Population
1.18 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6628511/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6628511/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6628511/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6628511/	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/062055Orig1s034.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/062055Orig1s034.pdf	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

Value	Dose	Analyte	Population
3.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6628511/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6628511/	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/062055Orig1s034.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/062055Orig1s034.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.48 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/062055Orig1s034.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/062055Orig1s034.pdf	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/1408521/	healthy, 12 years n = 1 Health Status: healthy Age Group: 12 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1408521/	Other AEs: Pancreatitis... Other AEs: Pancreatitis Sources: https://pubmed.ncbi.nlm.nih.gov/1408521/
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: https://pubmed.ncbi.nlm.nih.gov/16215473/	healthy, 15 years n = 1 Health Status: healthy Age Group: 15 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/16215473/	Other AEs: Pancreatitis... Other AEs: Pancreatitis Sources: https://pubmed.ncbi.nlm.nih.gov/16215473/
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: https://pubmed.ncbi.nlm.nih.gov/241119/	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: https://pubmed.ncbi.nlm.nih.gov/241119/	Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (2.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/241119/
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: https://pubmed.ncbi.nlm.nih.gov/241119/	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: https://pubmed.ncbi.nlm.nih.gov/241119/	Disc. AE: Nausea, Abdominal pain... AEs leading to discontinuation/dose reduction: Nausea (14.6%) Abdominal pain (4.9%) Sources: https://pubmed.ncbi.nlm.nih.gov/241119/
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: https://pubmed.ncbi.nlm.nih.gov/2140547/	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: https://pubmed.ncbi.nlm.nih.gov/2140547/	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: https://pubmed.ncbi.nlm.nih.gov/2140547/
100 mg single, intravenous Dose: 100 mg Route: intravenous Route: single Dose: 100 mg Sources: https://clinicaltrials.gov/ct2/show/NCT02005029	unhealthy n = 9 Health Status: unhealthy Condition: Parkinson's Disease Population Size: 9 Sources: https://clinicaltrials.gov/ct2/show/NCT02005029	Other AEs: Akathisia, Diarrhea... Other AEs: Akathisia (below serious, 1 patient) Diarrhea (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT02005029

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/1408521/	healthy, 12 years n = 1 Health Status: healthy Age Group: 12 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1408521/
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: https://pubmed.ncbi.nlm.nih.gov/16215473/	healthy, 15 years n = 1 Health Status: healthy Age Group: 15 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/16215473/
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: https://pubmed.ncbi.nlm.nih.gov/241119/	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: https://pubmed.ncbi.nlm.nih.gov/241119/
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: https://pubmed.ncbi.nlm.nih.gov/241119/	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: https://pubmed.ncbi.nlm.nih.gov/241119/
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: https://pubmed.ncbi.nlm.nih.gov/241119/	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: https://pubmed.ncbi.nlm.nih.gov/241119/
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: https://pubmed.ncbi.nlm.nih.gov/2140547/	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: https://pubmed.ncbi.nlm.nih.gov/2140547/
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: https://pubmed.ncbi.nlm.nih.gov/2140547/	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: https://pubmed.ncbi.nlm.nih.gov/2140547/
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: https://pubmed.ncbi.nlm.nih.gov/2140547/	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: https://pubmed.ncbi.nlm.nih.gov/2140547/
Akathisia	below serious, 1 patient	100 mg single, intravenous Dose: 100 mg Route: intravenous Route: single Dose: 100 mg Sources: https://clinicaltrials.gov/ct2/show/NCT02005029	unhealthy n = 9 Health Status: unhealthy Condition: Parkinson's Disease Population Size: 9 Sources: https://clinicaltrials.gov/ct2/show/NCT02005029
Diarrhea	below serious, 1 patient	100 mg single, intravenous Dose: 100 mg Route: intravenous Route: single Dose: 100 mg Sources: https://clinicaltrials.gov/ct2/show/NCT02005029	unhealthy n = 9 Health Status: unhealthy Condition: Parkinson's Disease Population Size: 9 Sources: https://clinicaltrials.gov/ct2/show/NCT02005029

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 P-gp 1461 OATP1B1 788 OATP1B3 706	CYP3A 191 OAT2 115

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9231305/	likely
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/050207s074,050611s036lbl.pdf#page=10; https://pubmed.ncbi.nlm.nih.gov/10608481/; https://pubmed.ncbi.nlm.nih.gov/9728898/; https://doi.org/10.1016/j.dmpk.2015.05.001 Page: 10.0	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; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/050207s074,050611s036lbl.pdf#page=10; https://pubmed.ncbi.nlm.nih.gov/10608481/; https://pubmed.ncbi.nlm.nih.gov/9728898/; https://doi.org/10.1016/j.dmpk.2015.05.001 Page: 10.0
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17296622/	yes [IC50 217 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18027988/	yes [IC50 22.7 uM]
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17296622/	yes [IC50 34 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OAT2 115	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15708966/	yes
CYP3A 191	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/050207s074,050611s036lbl.pdf#page=9 Page: 9.0	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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/050207s074,050611s036lbl.pdf#page=9 Page: 9.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/14674677/

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0126	http://www.3bsc.com/index/pro_info.php?id=19482
AEchem Scientific Corp., USA	AE061269	https://www.aechemsc.com/info_products/AE061269.php
AHH Chemical co.,ltd	API-1112	http://www.ahhchemical.com/product/API-1112.html
Aaron Chemicals	AR0039Z1	http://www.aaronchem.com/114-07-8
Achemtek	0104-008056	http://www.achemtek.com/114-07-8
Acorn PharmaTech	ACN-048190	http://www.acornpharmatech.com/
Acros Organics	AC227330050	https://www.fishersci.com/shop/products/erythromycin-98-acros-organics/AC227330050
Acros Organics	AC227330250	https://www.fishersci.com/shop/products/erythromycin-98-acros-organics/AC227330250
Acros Organics	AC227331000	https://www.fishersci.com/shop/products/erythromycin-98-acros-organics/AC227331000
Acros Organics	AC343880250	https://www.fishersci.com/shop/products/erythromycin-eur-ph-acros-organics-1/AC343880250
Acros Organics	AC343880050	https://www.fishersci.com/shop/products/erythromycin-eur-ph-acros-organics/AC343880050
Alfa Chemistry	AP114078	https://reagents.alfa-chemistry.com/product/erythromycin-cas-114-07-8-1997.html
Alfa Chemistry	AP114078-B	https://reagents.alfa-chemistry.com/product/erythromycin-cas-114-07-8-1999.html
Alfa Chemistry	AP114078-A	https://reagents.alfa-chemistry.com/product/erythromycin-standard-solution-cas-114-07-8-1998.html
Alfa Chemistry	114-07-8	https://www.alfa-chemistry.com/erythromycin-cas-114-07-8-item-289674.htm
ApexBio Technology	B1939	http://www.apexbt.com/erythromycin.html
Aurora Fine Chemicals LLC	A13.139.732	http://online.aurorafinechemicals.com/info?ID=A13.139.732
Avantor Inc	97061-220	https://us.vwr.com/store/catalog/product.jsp?catalog_number=97061-220
Avantor Inc	200006-440	https://us.vwr.com/store/product/18600820/erythromycin
BLD Pharm	BD17733	http://www.bldpharm.com/products/114-07-8.html
BioCrick	BCC4778	http://www.biocrick.com/Erythromycin-BCC4778.html
BioSynth	E-3250	https://www.biosynth.com/products/biochemistry/culture-media-additives/products/E-3250.html
Boerchem	BC205124	http://www.boerchem.com/?product_34527.html
CSNpharm	CSN12503	https://www.csnpharm.com/products/erythromycin.html
Chem Scene	CS-2168	http://www.chemscene.com/114-07-8.html
ChemMol	30102455	http://www.chemmol.com/chemmol/30102455.html
ChemMol	30102582	http://www.chemmol.com/chemmol/30102582.html
Chemchart	cc-erythromycin	http://chemchart.com/erythromycin-detail.html
Chemspace	CSSB00000053730	https://chem-space.com/CSSB00000053730
DC Chemicals	DC7409	http://www.dcchemicals.com/product_show-E_Mycin.html
Glentham Life Sciences	GA1145	http://www.glentham.com/products/product/GA1145/
Hairui	HR130758	http://www.hairuichem.com/en/product/114-07-8.html
LGC Standards	DRE-A13203490AL-100	https://www.lgcstandards.com/US/en/p/DRE-A13203490AL-100
LGC Standards	DRE-C13203490	https://www.lgcstandards.com/US/en/p/DRE-C13203490
Lab Network	LN00237041	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00237041
MedChem Express	HY-B0220	https://www.medchemexpress.com/Erythromycin.html
MuseChem	A000680	https://www.musechem.com/product/A000680.html
MuseChem	R007004	https://www.musechem.com/product/R007004.html
OChem	657	http://www.ocheminc.com/index.php?act=psearch&pid=114E078
Oakwood	94643	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=79817&ExtHyperLink=1
Parchem	16967	http://www.parchem.com/chemical-supplier-distributor/Erythromycin-006967.aspx
Parchem	10930	http://www.parchem.com/chemical-supplier-distributor/Erythromycines-000930.aspx
Shanghai Tauto Biotech Co., Ltd	E-0288	http://www.tautobiotech.com/BRM/eProductShow.asp?ArticleID=370
Sigma-Aldrich	45674_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/45674?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	BP794_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/bp794?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	E0774_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/e0774?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	45703_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/45703?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1242000_USP	https://www.sigmaaldrich.com/catalog/product/usp/1242000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S527402	http://www.smolecule.com/products/s527402
TCI (Tokyo Chemical Industry)	E0751	http://www.tcichemicals.com/eshop/en/us/commodity/E0751/index.html
THE BioTek	bt-267660	https://www.thebiotek.com/product/inhibitors/bt-267660
VladaChem	VL272699-25G	https://www.vladachem.com/product.php?products=114-07-8
Yuhao Chemical	HL1432	http://www.chemyuhao.com/114-07-8.html
abcr GmbH	AB251852	http://www.abcr.com/shop/en/AB251852
eNovation Chemicals	D565961	https://enovationchem.com/ProductDetails.asp?ProductID=D565961
eNovation Chemicals	D488558	https://www.enovationchem.com/ProductDetails.asp?ProductID=D488558
eNovation Chemicals	D916215	https://www.enovationchem.com/ProductDetails.asp?ProductID=D916215
iChemical	EBD28902	http://www.ichemical.com/products/114-07-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-4566208867	https://mcule.com/MCULE-4566208867/

PubMed

Title	Date	PubMed
A CLINICAL STUDY OF ERYTHROMYCIN STEARATE AND ERYTHROMYCIN ETHYL SUCCINATE IN OFFICE PRACTICE.	1964 Sep	14179191
A C-13 relaxation study on erythromycin A cyclic 11,12-carbonate.	1978 May	670091
Drug-induced gallbladder disease. Incidence, aetiology and management.	1992 Jan-Feb	1536697
The in-vitro activity of two new quinolones: rufloxacin and MF 961.	1992 Jun	1324239
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
Receptor for motilin identified in the human gastrointestinal system.	1999 Jun 25	10381885
Clinical efficacy of intravenous followed by oral azithromycin monotherapy in hospitalized patients with community-acquired pneumonia. The Azithromycin Intravenous Clinical Trials Group.	2000 Jul	10858333
[Blueberry muffin baby: the pathogenesis of cutaneous extramedullary hematopoiesis].	2001 Nov	11757459
Compound cardiac toxicity of oral erythromycin and verapamil.	2001 Nov	11724091
Risk of torsades de pointes from oral erythromycin with concomitant carbimazole (methimazole) administration.	2001 Oct	11707056
[A comparative study of various evaluation methods of the antibiotic sensitivity of strict anaerobic bacteria of the subgingival flora].	2001 Sep	11808376
Stereodivergent approach to beta-hydroxy alpha-amino acids from C(2)-symmetrical alk-2-yne-1,4-diols.	2002 Dec 12	12465925
Gamma-fluorinated analogues of glutamic acid and glutamine.	2003 Apr	12707806
Stereoselective biosynthesis of chloroarylpropane diols by the basidiomycete Bjerkandera adusta.	2003 Jul	12738275
Local mechanisms underlying the regulatory effect of Kropanol on hemopoiesis during paradoxical sleep deprivation.	2004 Feb	15273764
[Usefulness of oral exfoliative cytology for the diagnosis of oral squamous dysplasia and carcinoma].	2004 Mar	15107778
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	14971019
Mechanism of beta-silyl diacyl peroxide decomposition: a mild and stereoselective synthesis of beta-silyl esters.	2004 May 28	15152998
Initial (latent) polycythemia vera with thrombocytosis mimicking essential thrombocythemia.	2005	15983426
High volume bioassays to assess CYP3A4-mediated drug interactions: induction and inhibition in a single cell line.	2005 Jan	15466163
Cytotoxicity of neolignans identified in Saururus chinensis towards human cancer cell lines.	2005 May	15931587

Patents

Sample Use Guides

In Vivo Use Guide

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 14:59:52 GMT 2023` Edited by `admin` on `Fri Dec 15 14:59:52 GMT 2023`
Record UNII	Y7A95YRI88
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ERYTHROMYCIN THIOCYANATE

Common Name

English

ERYTHROMYCIN THIOCYANATE [GREEN BOOK]

Common Name

English

THIOCYANIC ACID, COMPD. WITH ERYTHROMYCIN (1:1)

Common Name

English

ERYTROVET

Brand Name

English

BACTENIX V 300

Brand Name

English

GALLIMYCIN

Brand Name

English

Code System Code Type Description

CAS

7704-67-8