THIAMPHENICOL GLYCINATE ACETYLCYSTEINE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H18Cl2N2O6S.C5H9NO3S
Molecular Weight	576.468
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of THIAMPHENICOL GLYCINATE ACETYLCYSTEINE

SMILES

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

InChI

InChIKey=PEGBMQRZXOKYCO-XGBIXHFLSA-N

InChI=1S/C14H18Cl2N2O6S.C5H9NO3S/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;1-3(7)6-4(2-10)5(8)9/h2-5,10,12-13,20H,6-7,17H2,1H3,(H,18,21);4,10H,2H2,1H3,(H,6,7)(H,8,9)/t10-,12-;4-/m10/s1

HIDE SMILES / InChI

Molecular Formula	C14H18Cl2N2O6S
Molecular Weight	413.274
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

Molecular Formula	C5H9NO3S
Molecular Weight	163.195
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
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 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

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PubMed

Show entries

Title	Date	PubMed
Effect of racephenicol on antibiotic resistance of lactose-fermenting enteric bacteria in chickens.	1973 Sep	4586141
Effects of florfenicol injection on the meat characteristics of the cervical muscles in cattle.	2002 Jan	16206782
Chloramphenicol and florfenicol susceptibility of fish-pathogenic bacteria isolated in France: comparison of minimum inhibitory concentration, using recommended provisory standards for fish bacteria.	2003	14633029
Rickettsia felis in the United Kingdom.	2003 Aug	12971375
In vitro effects of some antibiotics on glutathione reductase from sheep liver.	2003 Dec	15008519

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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).

Substance Class	Chemical
Record UNII	7I3XBP3IFP
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

L-CYSTEINE, N-ACETYL-, COMPD. WITH GLYCINE (2R,3R)-2-((2,2-DICHLOROACETYL)AMINO)-3-HYDROXY-3-(4-(METHYLSULFONYL)PHENYL)PROPYL ESTER (1:1)

Preferred Name

English

THIAMPHENICOL GLYCINATE ACETYLCYSTEINE

Common Name

English

Thiamphenicol glycinate acetylcysteine [WHO-DD]

Common Name

English

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Code System

Code

Type

Description

ECHA (EC/EINECS)

243-572-9

PRIMARY

FDA UNII

7I3XBP3IFP

PRIMARY

PUBCHEM

44147002

PRIMARY

SMS_ID

100000084824

PRIMARY

EVMPD

SUB04804MIG

PRIMARY

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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