U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

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

SHOW SMILES / InChI
Structure of THIAMPHENICOL

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
An assessment of chloramphenicol and thiamphenicol in the induction of aplastic anaemia in the BALB/c mouse.
2000 Oct
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
Serum soluble transferrin receptor concentration is an accurate estimate of the mass of tissue receptors.
2001 Jun
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
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
Recent clinical evidence of the efficacy and safety of thiamphenicol glycinate acetylcysteinate and thiamphenicol glycinate.
2002 Jun
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
Chloramphenicol and florfenicol susceptibility of fish-pathogenic bacteria isolated in France: comparison of minimum inhibitory concentration, using recommended provisory standards for fish bacteria.
2003
Rickettsia felis in the United Kingdom.
2003 Aug
Effect of oral enrofloxacin and florfenicol on pigs experimentally infected with Actinobacillus pleuropneumoniae serotype 1.
2003 Jun
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
Bioavailability and pharmacokinetics of florfenicol in broiler chickens.
2003 Oct
Comparative plasma pharmacokinetics and tolerance of florfenicol following intramuscular and intravenous administration to camels, sheep and goats.
2003 Sep
Mobile genes coding for efflux-mediated antimicrobial resistance in Gram-positive and Gram-negative bacteria.
2003 Sep
Gonorrhoea surveillance system in France: 1986-2000.
2004 Apr
[Construction of SW480 cell model identifying Shigella virulent genes].
2004 Jul
Molecular basis of bacterial resistance to chloramphenicol and florfenicol.
2004 Nov
Influence of thiamphenicol on the primary functions of human polymorphonuclear leucocytes against Streptococcus pyogenes.
2004 Oct
Resistance pattern and assessment of phenicol agents' minimum inhibitory concentration in multiple drug resistant Chryseobacterium isolates from fish and aquatic habitats.
2005
Plasmid-borne florfenicol resistance in Pasteurella multocida.
2005 May
Determination of florfenicol in fish feed by liquid chromatography.
2005 Nov-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
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
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
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 17:18:32 GMT 2023
Edited
by admin
on Sat Dec 16 17:18:32 GMT 2023
Record UNII
FLQ7571NPM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIAMPHENICOL
EP   INN   JAN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
Thiamphenicol [WHO-DD]
Common Name English
ACETAMIDE, 2,2-DICHLORO-N-((1R,2R)-2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-(METHYLSULFONYL)PHENYL)ETHYL)-
Systematic Name English
thiamphenicol [INN]
Common Name English
THIOCYMETIN
Brand Name English
ARMAI
Brand Name English
THIAMPHENICOL [MART.]
Common Name English
NSC-522822
Code English
THIAMPHENICOL [MI]
Common Name English
THIAMPHENICOL [JAN]
Common Name English
WIN-5063-2
Code English
THIAMPHENICOL [EP MONOGRAPH]
Common Name English
THIAMPHENICOL [USAN]
Common Name English
2,2-DICHLORO-N-((1R,2R)-2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-(METHYLSULFONYL)PHENYL)ETHYL)ACETAMIDE
Common Name English
Classification Tree Code System Code
WHO-VATC QJ51BA02
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
WHO-ATC J01BA52
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
NCI_THESAURUS C258
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
WHO-ATC J01BA02
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
WHO-VATC QJ01BA02
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
WHO-VATC QJ01BA52
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID5021338
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
CAS
15318-45-3
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
NSC
522822
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
ChEMBL
CHEMBL1236282
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
WIKIPEDIA
THIAMPHENICOL
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
RXCUI
10463
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m10723
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY Merck Index
INN
935
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
NCI_THESAURUS
C61969
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
CHEBI
32215
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
EVMPD
SUB10970MIG
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
DRUG BANK
DB08621
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
DRUG CENTRAL
2624
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
FDA UNII
FLQ7571NPM
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
ECHA (EC/EINECS)
239-355-3
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
SMS_ID
100000082417
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
PUBCHEM
27200
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
MESH
D013839
Created by admin on Sat Dec 16 17:18:33 GMT 2023 , Edited by admin on Sat Dec 16 17:18:33 GMT 2023
PRIMARY
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