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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H18Cl2N2O6S.C5H9NO3S
Molecular Weight 576.468
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIAMPHENICOL GLYCINATE ACETYLCYSTEINE

SMILES

CC(=O)N[C@@H](CS)C(O)=O.CS(=O)(=O)C1=CC=C(C=C1)[C@@H](O)[C@@H](COC(=O)CN)NC(=O)C(Cl)Cl

InChI

InChIKey=PEGBMQRZXOKYCO-XGBIXHFLSA-N
InChI=1S/C14H18Cl2N2O6S.C5H9NO3S/c1-25(22,23)9-4-2-8(3-5-9)12(20)10(7-24-11(19)6-17)18-14(21)13(15)16;1-3(7)6-4(2-10)5(8)9/h2-5,10,12-13,20H,6-7,17H2,1H3,(H,18,21);4,10H,2H2,1H3,(H,6,7)(H,8,9)/t10-,12-;4-/m10/s1

HIDE SMILES / InChI

Molecular Formula C14H18Cl2N2O6S
Molecular Weight 413.274
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7447408

Thiamphenicol is a broad-spectrum antibiotic, which is active against gram-positive and gram-negative organisms. The drug is marketed in Asia and Latin America for the treatment of various infections, including sexually transmitted diseases. As many phenicols, thiamphenicol inhibits the protein synthesis in bacterias by binding to 23S ribosomal subunit. In Europe and USA the drug is used in a veterinary practice.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.3 µM [Kd]
2.3 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
GLITISOL

Approved Use

This medication is indicated for the treatment of respiratory, genitourinary, hepatobiliary, surgical, soft tissue, otolaryngological (rhinosinusitis, pharyngitis, laryngitis), typhoid, paratyphoid infections, purulent meningitis, brucellosis, sexually transmitted diseases (gonococcal and non-gonococcal urethritis, donovanose, lymphogranuloma venereum), pelvic inflammatory disease, vulvovaginitis, cervicovaginitis and bacterial vaginosis caused by microorganisms sensitive to thiamphenicol.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8.3 μg/mL
0.5 g single, intramuscular
dose: 0.5 g
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
5.6 μg/mL
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
32.3 μg/mL
1.5 g single, intramuscular
dose: 1.5 g
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
17.6 μg/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
5.6 μg/mL
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
5.9 μg/mL
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
18.6 μg/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
16.7 μg/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
17.6 μg/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
16.1 μg/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
17.8 μg/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
30.1 μg × h/mL
0.5 g single, intravenous
dose: 0.5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
34 μg × h/mL
0.5 g single, intramuscular
dose: 0.5 g
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
29.4 μg × h/mL
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
117.1 μg × h/mL
1.5 g single, intramuscular
dose: 1.5 g
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
167.3 μg × h/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
29.4 μg × h/mL
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
28.8 μg × h/mL
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
149.1 μg × h/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
167.3 μg × h/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
158.9 μg × h/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
178.6 μg × h/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
171.6 μg × h/mL
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.1 h
0.5 g single, intravenous
dose: 0.5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2.8 h
0.5 g single, intramuscular
dose: 0.5 g
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2.7 h
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3.2 h
1.5 g single, intramuscular
dose: 1.5 g
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
6.1 h
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2.7 h
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2.6 h
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
5.1 h
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
6.1 h
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
6 h
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
7.3 h
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
6.9 h
2.5 g single, oral
dose: 2.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
90%
THIAMPHENICOL serum
Homo sapiens
100%
THIAMPHENICOL plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
2.5 g 1 times / day multiple, oral
Recommended
Dose: 2.5 g, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
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, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Effect of racephenicol on antibiotic resistance of lactose-fermenting enteric bacteria in chickens.
1973 Sep
Inhibition of mitochondrial protein synthesis promotes autonomous regulation of mtDNA expression and generation of a new mitochondrial RNA species.
2001 Apr 13
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
The effects of certain antibiotics on biogas production in the anaerobic digestion of pig waste slurry.
2002 Apr
Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995.
2002 Apr
Pharmacokinetics of thiamphenicol in pigs.
2002 Dec
A comparative kinetic study of thiamphenicol in pre-ruminant lambs and calves.
2002 Dec
Haemotoxicity of thiamphenicol in the BALB/c mouse and Wistar Hanover rat.
2002 Dec
Clinical efficacy of florfenicol in the treatment of calf respiratory tract infections.
2002 Feb
Residue depletion of thiamphenicol in the sea-bass.
2002 Feb
Effects of vaccination prior to transit and administration of florfenicol at time of arrival in a feedlot on the health of transported calves and detection of Mannheimia haemolytica in nasal secretions.
2002 Feb
Effects of florfenicol injection on the meat characteristics of the cervical muscles in cattle.
2002 Jan
Molecular analysis of chromosomally florfenicol-resistant Escherichia coli isolates from France and Germany.
2002 Jan
Pyrrole analogues of chloramphenicol. III. Synthesis and antibacterial activity of DL-threo-1-(1-methylsulfonylpyrrole-3-yl)-2-dichloroacetamidopropane-1,3-diol.
2002 Mar-Apr
Liquid chromatographic determination of florfenicol in the plasma of multiple species of fish.
2002 Nov 15
Pharmacokinetics of florfenicol in healthy and Escherichia coli-infected broiler chickens.
2002 Oct
Antimicrobial susceptibilities of Neisseria gonorrhoeae strains isolated in Java, Indonesia.
2003 Jan
Plasmid-mediated florfenicol and ceftriaxone resistance encoded by the floR and bla(CMY-2) genes in Salmonella enterica serovars Typhimurium and Newport isolated in the United States.
2004 Apr 15
Pharmacokinetics and bioavailability of florfenicol following intravenous, intramuscular and oral administrations in rabbits.
2004 Aug
The effect of testosterone propionate supplement on testicular toxicity with thiamphenicol in male Sprague-Dawley rats.
2004 Aug
Effects of subinhibitory concentrations of florfenicol on morphology, growth, and viability of Staphylococcus aureus.
2004 Aug
Intravenous and subcutaneous pharmacokinetics of florfenicol in sheep.
2004 Aug
Monitoring of florfenicol susceptibility among bovine and porcine respiratory tract pathogens collected in Germany during the years 2002 and 2003.
2004 Aug
Subinhibitory concentrations of florfenicol enhance the adherence of florfenicol-susceptible and florfenicol-resistant Staphylococcus aureus.
2004 Jul
Molecular basis of bacterial resistance to chloramphenicol and florfenicol.
2004 Nov
Optimization and validation of a micellar electrokinetic chromatographic method for the analysis of florfenicol.
2004 Nov 15
In vitro activity of thiamphenicol, erythromycin and fluoroquinolones against Legionella pneumophila.
2004 Oct
Pharmacokinetics of florfenicol in North American elk (Cervus elaphus).
2004 Oct
Influence of thiamphenicol on the primary functions of human polymorphonuclear leucocytes against Streptococcus pyogenes.
2004 Oct
Gene cloning and properties of the RND-type multidrug efflux pumps MexPQ-OpmE and MexMN-OprM from Pseudomonas aeruginosa.
2005
Molecular evaluation of antibiotic susceptibility of Tropheryma whipplei in axenic medium.
2005 Feb
Determination of florfenicol in fish feed by liquid chromatography.
2005 Nov-Dec
Assessing the effect of a single dose florfenicol treatment in feedlot cattle on the antimicrobial resistance patterns in faecal Escherichia coli.
2005 Sep-Dec
Evaluation of the therapeutic activity of tulathromycin against swine respiratory disease on farms in Europe.
2005 Summer
Differential stability of mitochondrial mRNA in HeLa cells.
2006
Role of coresistance in the development of resistance to chloramphenicol in Escherichia coli isolated from sick cattle and pigs.
2006 Feb
Pharmacokinetics of florfenicol and its metabolite, florfenicol amine, in the Korean catfish (Silurus asotus).
2006 Feb
Three cases of occupational asthma induced by thiamphenicol: detection of serum-specific IgE.
2006 Mar
Patents

Sample Use Guides

100 or 200 g/ton
Route of Administration: Oral
In Vitro Use Guide
The minimum inhibitory concentrations (MIC50s) of thiamphenicol for different bacterial strains were: 100 ug/ml (E.coli), 3.1 ug/ml (Klebsiella), 100 ug/ml (Enterobacter), 100 ug/ml (Citrobacter), 200 ug/ml (Proteus mirabilis), 50 ug/ml (Proteus, indole positive), 3.1 ug/ml (Shigella), 50 ug/ml (Salmonella), 6.3 ug/ml (Bacteroides), 25 ug/ml (S. aureus), 6.3 ug/ml (Enterococci), 1.6 ug/ml (H. influenzae), 6.3 ug/ml (Neisseria gonorrhoeae).
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:21:19 GMT 2025
Edited
by admin
on Mon Mar 31 19:21:19 GMT 2025
Record UNII
7I3XBP3IFP
Record Status Validated (UNII)
Record Version
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Name Type Language
L-CYSTEINE, N-ACETYL-, COMPD. WITH GLYCINE (2R,3R)-2-((2,2-DICHLOROACETYL)AMINO)-3-HYDROXY-3-(4-(METHYLSULFONYL)PHENYL)PROPYL ESTER (1:1)
Preferred Name English
THIAMPHENICOL GLYCINATE ACETYLCYSTEINE
WHO-DD  
Common Name English
Thiamphenicol glycinate acetylcysteine [WHO-DD]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
243-572-9
Created by admin on Mon Mar 31 19:21:19 GMT 2025 , Edited by admin on Mon Mar 31 19:21:19 GMT 2025
PRIMARY
FDA UNII
7I3XBP3IFP
Created by admin on Mon Mar 31 19:21:19 GMT 2025 , Edited by admin on Mon Mar 31 19:21:19 GMT 2025
PRIMARY
PUBCHEM
44147002
Created by admin on Mon Mar 31 19:21:19 GMT 2025 , Edited by admin on Mon Mar 31 19:21:19 GMT 2025
PRIMARY
SMS_ID
100000084824
Created by admin on Mon Mar 31 19:21:19 GMT 2025 , Edited by admin on Mon Mar 31 19:21:19 GMT 2025
PRIMARY
EVMPD
SUB04804MIG
Created by admin on Mon Mar 31 19:21:19 GMT 2025 , Edited by admin on Mon Mar 31 19:21:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID10942260
Created by admin on Mon Mar 31 19:21:19 GMT 2025 , Edited by admin on Mon Mar 31 19:21:19 GMT 2025
PRIMARY
CAS
20192-91-0
Created by admin on Mon Mar 31 19:21:19 GMT 2025 , Edited by admin on Mon Mar 31 19:21:19 GMT 2025
PRIMARY
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