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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.
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
Antimicrobial susceptibilities and plasmid patterns of Neisseria gonorrhoeae in Bénin.
2001 Feb
Allometric analysis of thiamphenicol disposition among seven mammalian species.
2001 Jun
Chronotoxicology of florfenicol.
2001 May
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Antimicrobial susceptibility of Pasteurella multocida isolated from cattle and pigs.
2001 Sep
Antimicrobial susceptibilities of Neisseria gonorrhoeae in Kigali, Rwanda, and trends of resistance between 1986 and 2000.
2001 Sep
Evaluation of certain veterinary drug residues in food.
2002
Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995.
2002 Apr
Relationship of vitamin E supplementation and antimicrobial treatment with acute-phase protein responses in cattle affected by naturally acquired respiratory tract disease.
2002 Aug
Haemotoxicity of thiamphenicol in the BALB/c mouse and Wistar Hanover rat.
2002 Dec
Florfenicol resistance in Salmonella enterica serovar Newport mediated by a plasmid related to R55 from Klebsiella pneumoniae.
2003 Apr
In vitro effects of some antibiotics on glutathione reductase from sheep liver.
2003 Dec
Stability of florfenicol in drinking water.
2003 Jan-Feb
Pharmacokinetics of florfenicol in loggerhead sea turtles (Caretta caretta) after single intravenous and intramuscular injections.
2003 Mar
Determination of florfenicol amine in channel catfish muscle by liquid chromatography.
2003 May-Jun
Serogroup A Neisseria meningitidis outside meningitis belt in southwest Cameroon.
2003 Oct
[Role of thiamphenicol in the treatment of community-acquired lung infections].
2004
Intravenous and subcutaneous pharmacokinetics of florfenicol in sheep.
2004 Aug
Subinhibitory concentrations of florfenicol enhance the adherence of florfenicol-susceptible and florfenicol-resistant Staphylococcus aureus.
2004 Jul
Gene cloning and properties of the RND-type multidrug efflux pumps MexPQ-OpmE and MexMN-OprM from Pseudomonas aeruginosa.
2005
Resistance pattern and assessment of phenicol agents' minimum inhibitory concentration in multiple drug resistant Chryseobacterium isolates from fish and aquatic habitats.
2005
Effects of some antibiotics on glutathione reductase activities from human erythrocytes in vitro and from rat erythrocytes in vivo.
2005 Feb
Molecular evaluation of antibiotic susceptibility of Tropheryma whipplei in axenic medium.
2005 Feb
[Analysis of chloramphenicol, thiamphenicol and florfenicol in chicken by high performance liquid chromatography with electrospray ionization mass spectrometry].
2005 Jan
Pharmacokinetics of florfenicol in the red pacu (Piaractus brachypomus) after single dose intramuscular administration.
2005 Jun
Determination of florfenicol in fish feed by liquid chromatography.
2005 Nov-Dec
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
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 Sat Dec 16 16:52:12 GMT 2023
Edited
by admin
on Sat Dec 16 16:52:12 GMT 2023
Record UNII
283383NO13
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
RACEFENICOL
INN  
INN  
Official 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 Sat Dec 16 16:52:12 GMT 2023 , Edited by admin on Sat Dec 16 16:52:12 GMT 2023
Code System Code Type Description
PUBCHEM
27200
Created by admin on Sat Dec 16 16:52:12 GMT 2023 , Edited by admin on Sat Dec 16 16:52:12 GMT 2023
PRIMARY
CAS
847-25-6
Created by admin on Sat Dec 16 16:52:12 GMT 2023 , Edited by admin on Sat Dec 16 16:52:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL315338
Created by admin on Sat Dec 16 16:52:12 GMT 2023 , Edited by admin on Sat Dec 16 16:52:12 GMT 2023
PRIMARY
SMS_ID
100000080305
Created by admin on Sat Dec 16 16:52:12 GMT 2023 , Edited by admin on Sat Dec 16 16:52:12 GMT 2023
PRIMARY
INN
2546
Created by admin on Sat Dec 16 16:52:12 GMT 2023 , Edited by admin on Sat Dec 16 16:52:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID401033713
Created by admin on Sat Dec 16 16:52:12 GMT 2023 , Edited by admin on Sat Dec 16 16:52:12 GMT 2023
PRIMARY
NCI_THESAURUS
C61920
Created by admin on Sat Dec 16 16:52:12 GMT 2023 , Edited by admin on Sat Dec 16 16:52:12 GMT 2023
PRIMARY
FDA UNII
283383NO13
Created by admin on Sat Dec 16 16:52:12 GMT 2023 , Edited by admin on Sat Dec 16 16:52:12 GMT 2023
PRIMARY
EVMPD
SUB10231MIG
Created by admin on Sat Dec 16 16:52:12 GMT 2023 , Edited by admin on Sat Dec 16 16:52:12 GMT 2023
PRIMARY
MERCK INDEX
m10723
Created by admin on Sat Dec 16 16:52:12 GMT 2023 , Edited by admin on Sat Dec 16 16:52:12 GMT 2023
PRIMARY Merck Index
Related Record Type Details
ENANTIOMER -> RACEMATE
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ACTIVE MOIETY