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

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 180	Inhibitor 8,504		2.3 µM [Kd]
Bacterial 70S ribosome 180	Inhibitor 8,504		2.3 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235	Curative		Not Provided 511	Unknown
Bacterial infections 235	Curative		Approved 8,583	GLITISOL

C_max

Value	Dose	Analyte	Population
8.3 μg/mL	0.5 g single, intramuscular	THIAMPHENICOL plasma	Homo sapiens
5.6 μg/mL	0.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
32.3 μg/mL	1.5 g single, intramuscular	THIAMPHENICOL plasma	Homo sapiens
17.6 μg/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
5.6 μg/mL	0.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
5.9 μg/mL	0.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
18.6 μg/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
16.7 μg/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
17.6 μg/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
16.1 μg/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
17.8 μg/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
30.1 μg × h/mL	0.5 g single, intravenous	THIAMPHENICOL plasma	Homo sapiens
34 μg × h/mL	0.5 g single, intramuscular	THIAMPHENICOL plasma	Homo sapiens
29.4 μg × h/mL	0.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
117.1 μg × h/mL	1.5 g single, intramuscular	THIAMPHENICOL plasma	Homo sapiens
167.3 μg × h/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
29.4 μg × h/mL	0.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
28.8 μg × h/mL	0.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
149.1 μg × h/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
167.3 μg × h/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
158.9 μg × h/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
178.6 μg × h/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
171.6 μg × h/mL	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
2.1 h	0.5 g single, intravenous	THIAMPHENICOL plasma	Homo sapiens
2.8 h	0.5 g single, intramuscular	THIAMPHENICOL plasma	Homo sapiens
2.7 h	0.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
3.2 h	1.5 g single, intramuscular	THIAMPHENICOL plasma	Homo sapiens
6.1 h	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
2.7 h	0.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
2.6 h	0.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
5.1 h	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
6.1 h	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
6 h	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
7.3 h	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens
6.9 h	2.5 g single, oral	THIAMPHENICOL plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
90%			THIAMPHENICOL serum	Homo sapiens
100%			THIAMPHENICOL plasma	Homo sapiens

Doses

Doses

Show entries

Dose	Population	Adverse events
2.5 g 1 times / day multiple, oral Recommended	unhealthy, ADULT
500 mg 3 times / day multiple, oral Recommended	unhealthy, ADULT

Showing 1 to 2 of 2 entries

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PubMed

Show entries

Title	Date	PubMed
Antimicrobial activity of thiamphenicol-glycinate-acetylcysteinate and other drugs against Chlamydia pneumoniae.	2001	11304944
Antimicrobial susceptibilities and plasmid patterns of Neisseria gonorrhoeae in Bénin.	2001 Feb	11236110
Serum soluble transferrin receptor concentration is an accurate estimate of the mass of tissue receptors.	2001 Jun	11378262
Chronotoxicology of florfenicol.	2001 May	11475424
Antimicrobial susceptibilities of Neisseria gonorrhoeae in Kigali, Rwanda, and trends of resistance between 1986 and 2000.	2001 Sep	11518873

Showing 1 to 5 of 20 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).

Show entries

Name

Type

Language

ARMAI

Preferred Name

English

THIAMPHENICOL

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

Showing 1 to 5 of 14 entries

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Show entries

Classification Tree

Code System

Code

Amphenicols

WHO-VATC

QJ51BA02

Amphenicols

WHO-ATC

J01BA52

Anti-Infective Agent

NCI_THESAURUS

C258

Amphenicols

WHO-ATC

J01BA02

Amphenicols

WHO-VATC

QJ01BA02

Showing 1 to 5 of 6 entries

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Show entries

Code System

Code

Type

Description

EPA CompTox

DTXSID5021338

PRIMARY

CAS

15318-45-3

PRIMARY

NSC

522822

PRIMARY

ChEMBL

CHEMBL1236282

PRIMARY

WIKIPEDIA

THIAMPHENICOL

PRIMARY

Showing 1 to 5 of 18 entries

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ACTIVE MOIETY


					FLQ7571NPM

THIAMPHENICOL

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound