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Details

Stereochemistry RACEMIC
Molecular Formula C12H15Cl2NO5S
Molecular Weight 356.222
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACEPHENICOL

SMILES

CS(=O)(=O)C1=CC=C(C=C1)[C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl

InChI

InChIKey=OTVAEFIXJLOWRX-NXEZZACHSA-N
InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1

HIDE SMILES / InChI

Molecular Formula C12H15Cl2NO5S
Molecular Weight 356.222
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
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
Comparative in vitro activity of thiamphenicol-glycinate and thiamphenicol-glycinate-acetylcysteinate and other antimicrobials against respiratory pathogens.
2001
A simple classification method for residual antibiotics using E. coli cells transformed by the calcium chloride method and drug resistance plasmid DNA.
2001
Molecular features determining lymphocyte reactivity in allergic contact dermatitis to chloramphenicol and azidamphenicol.
2001 Jan
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Antimicrobial susceptibilities of Neisseria gonorrhoeae in Kigali, Rwanda, and trends of resistance between 1986 and 2000.
2001 Sep
Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995.
2002 Apr
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 florfenicol injection on the meat characteristics of the cervical muscles in cattle.
2002 Jan
An open, comparative pilot study of thiamphenicol glycinate hydrochloride vs clarithromycin in the treatment of acute lower respiratory tract infections due to Chlamydia pneumoniae.
2002 Jun
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
Chloramphenicol and florfenicol susceptibility of fish-pathogenic bacteria isolated in France: comparison of minimum inhibitory concentration, using recommended provisory standards for fish bacteria.
2003
Effect of oral enrofloxacin and florfenicol on pigs experimentally infected with Actinobacillus pleuropneumoniae serotype 1.
2003 Jun
Bioavailability and pharmacokinetics of florfenicol in broiler chickens.
2003 Oct
Mobile genes coding for efflux-mediated antimicrobial resistance in Gram-positive and Gram-negative bacteria.
2003 Sep
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
In vitro activity of thiamphenicol, erythromycin and fluoroquinolones against Legionella pneumophila.
2004 Oct
Gene cloning and properties of the RND-type multidrug efflux pumps MexPQ-OpmE and MexMN-OprM from Pseudomonas aeruginosa.
2005
A new mechanism for chloramphenicol, florfenicol and clindamycin resistance: methylation of 23S ribosomal RNA at A2503.
2005 Aug
Effects of some antibiotics on glutathione reductase activities from human erythrocytes in vitro and from rat erythrocytes in vivo.
2005 Feb
[Analysis of chloramphenicol, thiamphenicol and florfenicol in chicken by high performance liquid chromatography with electrospray ionization mass spectrometry].
2005 Jan
Determination of florfenicol in fish feed by liquid chromatography.
2005 Nov-Dec
Comparative evaluation between capillary electrophoresis and high-performance liquid chromatography for the analysis of florfenicol in plasma.
2005 Oct 4
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
Comparative efficacy of tulathromycin versus florfenicol and tilmicosin against undifferentiated bovine respiratory disease in feedlot cattle.
2005 Summer
Comparative efficacy of tulathromycin, tilmicosin, and florfenicol in the treatment of bovine respiratory disease in stocker cattle.
2005 Summer
Efficacy of tulathromycin compared with tilmicosin and florfenicol for the control of respiratory disease in cattle at high risk of developing bovine respiratory disease.
2005 Summer
Efficacy of tulathromycin in the treatment and prevention of natural outbreaks of bovine respiratory disease in European cattle.
2005 Summer
Differential stability of mitochondrial mRNA in HeLa cells.
2006
Pharmacokinetics of florfenicol in pigs following intravenous, intramuscular or oral administration and the effects of feed intake on oral dosing.
2006 Apr
Placental transfer of antibiotics administered to the mother: a review.
2006 Feb
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
Simultaneous analysis of thiamphenicol and its prodrug thiamphenicol glycinate in human plasma and urine by high performance liquid chromatography: application to pharmacokinetic study.
2006 Jun 7
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 Wed Apr 02 08:28:48 GMT 2025
Edited
by admin
on Wed Apr 02 08:28:48 GMT 2025
Record UNII
283383NO13
Record Status Validated (UNII)
Record Version
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Name Type Language
RACEFENICOL
INN  
INN  
Preferred Name English
RACEPHENICOL
USAN  
USAN  
Official Name English
RACEOPHENIDOL
Common Name English
(±)-THIAMPHENICOL
Common Name English
DEXAWIN
Brand Name English
racefenicol [INN]
Common Name English
RACEPHENICOL [USAN]
Common Name English
THIAMPHENICOL DL-FORM
MI  
Common Name English
THIAMPHENICOL DL-FORM [MI]
Common Name English
WIN-5063
Code English
WIN 5063
Code English
ACETAMIDE, 2,2-DICHLORO-N-(.BETA.-HYDROXY-.ALPHA.-(HYDROXYMETHYL)-P-(METHYLSULFONYL)PHENETHYL)-, THREO-(±)-
Common Name English
ACETAMIDE, 2,2-DICHLORO-N-(2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-(METHYLSULFONYL)PHENYL)ETHYL)-, (R*,R*)-(±)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C258
Created by admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
Code System Code Type Description
CAS
847-25-6
Created by admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
PRIMARY
ChEMBL
CHEMBL315338
Created by admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
PRIMARY
SMS_ID
100000080305
Created by admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
PRIMARY
INN
2546
Created by admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID401033713
Created by admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
PRIMARY
NCI_THESAURUS
C61920
Created by admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
PRIMARY
FDA UNII
283383NO13
Created by admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
PRIMARY
EVMPD
SUB10231MIG
Created by admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
PRIMARY
MERCK INDEX
m10723
Created by admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
PRIMARY Merck Index
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