THIAMPHENICOL AMINOACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H18Cl2N2O6S
Molecular Weight	413.274
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=AMGKHLVPQHMHGQ-ZYHUDNBSSA-N

InChI=1S/C14H18Cl2N2O6S/c1-25(22,23)9-4-2-8(3-5-9)12(20)10(7-24-11(19)6-17)18-14(21)13(15)16/h2-5,10,12-13,20H,6-7,17H2,1H3,(H,18,21)/t10-,12-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C14H18Cl2N2O6S
Molecular Weight	413.274
Charge	0
Count

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

Description
Sources: http://www.mims.com/thailand/drug/info/urfamycin
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15224555 and https://www.drugs.com/international/urfamycin.html

Thiamphenicol aminoacetate is an antibiotic. It is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. It is used in many countries as a veterinary antibiotic, but is available in China, Morocco and Italy for use in humans. Thiamphenicol aminoacetate is reported as an ingredient of Urfamycin in Ecuador, Indonesia, Italy, Taiwan, Thailand, Turkey, Japan. It is indicated for the treatment of GUT, hepatobiliary, respiratory tract, enteric tract infections, typhoid, paratyphoid fever and salmonellosis, brucellosis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neisseria gonorrhoeae growth 2 Target ID: Neisseria gonorrhoeae growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/2113717	Inhibitor 8297
Moraxella catarrhalis growth 2 Target ID: Moraxella catarrhalis growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/11367873	Inhibitor 8297
Streptococcus pneumoniae growth 20 Target ID: Streptococcus pneumoniae growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/11367873	Inhibitor 8297
Haemophilus influenzae growth 4 Target ID: Haemophilus influenzae growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/11367873	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Respiratory tract infections 85 Sources: http://www.mims.com/thailand/drug/info/urfamycin	Curative	Approved 8429	Urfamycin Approved Use GUT, hepatobiliary, resp tract, enteric tract infections, typhoid, paratyphoid fever & salmonellosis, brucellosis.
Salmonellosis 5 Sources: http://www.mims.com/thailand/drug/info/urfamycin	Curative	Approved 8429	Urfamycin Approved Use GUT, hepatobiliary, resp tract, enteric tract infections, typhoid, paratyphoid fever & salmonellosis, brucellosis.
Brucellosis 5 Sources: http://www.mims.com/thailand/drug/info/urfamycin	Curative	Approved 8429	Urfamycin Approved Use GUT, hepatobiliary, resp tract, enteric tract infections, typhoid, paratyphoid fever & salmonellosis, brucellosis.

PubMed

Title	Date	PubMed
[Re-evaluation of single-dose treatment with thiamphenicol and spectinomycin of uncomplicated male gonococcal urethritis].	1987	2962529
Comparative in vitro activity of thiamphenicol-glycinate and thiamphenicol-glycinate-acetylcysteinate and other antimicrobials against respiratory pathogens.	2001	11367873

Patents

Sample Use Guides

In Vivo Use Guide

Adult 500 mg 8 hrly. Childn 20-30 mg/kg/day. Gonorrhea 2.5 g/day for 1-2 days.

Route of Administration: Oral

In Vitro Use Guide

THIAMPHENICOL AMINOACETATE inhibited M. catarrhalis with MIC90 0.5 ug/ml

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:07:02 UTC 2023` Edited by `admin` on `Fri Dec 15 19:07:02 UTC 2023`
Record UNII	W5H94CY6V6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIAMPHENICOL AMINOACETATE

Common Name

English

THIOPHENICOL GLYCINATE

Common Name

English

Thiamphenicol aminoacetate [WHO-DD]

Common Name

English

THIAMPHENICOL GLYCINE ESTER

Common Name

English

GLYCINE, (2R,3R)-2-((2,2-DICHLOROACETYL)AMINO)-3-HYDROXY-3-(4-(METHYLSULFONYL)PHENYL)PROPYL ESTER

Common Name

English

THIAMPHENICOL GLYCINATE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID7048326