THIAMPHENICOL

Possibly Marketed Outside US

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179	Inhibitor 8,297		2.3 µM [Kd]
Bacterial 70S ribosome 179	Inhibitor 8,297		2.3 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234	Curative		Not Provided 504	Unknown
Bacterial infections 234	Curative		Approved 8,429	GLITISOL

PubMed

Show entries

Title	Date	PubMed
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Antimicrobial susceptibilities of Neisseria gonorrhoeae in Kigali, Rwanda, and trends of resistance between 1986 and 2000.	2001 Sep	11518873
The effects of certain antibiotics on biogas production in the anaerobic digestion of pig waste slurry.	2002 Apr	12003325
Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995.	2002 Apr	11971772
A comparative kinetic study of thiamphenicol in pre-ruminant lambs and calves.	2002 Dec	12443688

Showing 1 to 5 of 23 entries

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Patents

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).