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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.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 2.3 µM [Kd]
Inhibitor
8297
 2.3 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Not Provided
504
Unknown

Approved Use

Unknown
Curative
Approved
8429
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
Effects of florfenicol injection on the meat characteristics of the cervical muscles in cattle.
2002 Jan
In vitro effects of some antibiotics on glutathione reductase from sheep liver.
2003 Dec
In vitro evaluation of the susceptibility of Edwardsiella ictaluri, etiological agent of enteric septicemia in channel catfish, Ictalurus punctatus (Rafinesque), to florfenicol.
2003 Nov
[Role of thiamphenicol in the treatment of community-acquired lung infections].
2004
Gonorrhoea surveillance system in France: 1986-2000.
2004 Apr
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
Molecular analysis of florfenicol-resistant Escherichia coli isolates from pigs.
2004 Jan
[Construction of SW480 cell model identifying Shigella virulent genes].
2004 Jul
Subinhibitory concentrations of florfenicol enhance the adherence of florfenicol-susceptible and florfenicol-resistant Staphylococcus aureus.
2004 Jul
Characterization of florfenicol resistance among calf pathogenic Escherichia coli.
2004 Jul 15
Bioavailability and pharmacokinetics of florfenicol in healthy sheep.
2004 Jun
Use of florfenicol in non-human primates.
2004 Jun
Rickettsia felis, Bartonella henselae, and B. clarridgeiae, New Zealand.
2004 May
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
Resistance pattern and assessment of phenicol agents' minimum inhibitory concentration in multiple drug resistant Chryseobacterium isolates from fish and aquatic habitats.
2005
A new mechanism for chloramphenicol, florfenicol and clindamycin resistance: methylation of 23S ribosomal RNA at A2503.
2005 Aug
Fusobacterium nucleatum apoptosis-inducing outer membrane protein.
2005 Aug
Molecular basis of florfenicol-induced increase in adherence of Staphylococcus aureus strain Newman.
2005 Aug
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
Evaluation of the antimicrobial activity of florfenicol against bacteria isolated from bovine and porcine respiratory disease.
2005 Mar 20
Plasmid-borne florfenicol resistance in Pasteurella multocida.
2005 May
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

Patents

JPS6379822A
3
WO2004004658
3

Sample Use Guides

In Vivo Use Guide
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
Related Record Type Details
Structure of RACEPHENICOL
RACEMATE -> ENANTIOMER
Related Record Type Details
2-AMINO-1-(4-(METHYLSULFONYL)PHENYL)PROPANE-1,3-DIOL
IMPURITY -> PARENT
Related Record Type Details
Structure of THIAMPHENICOL
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