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

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 8504
Moraxella catarrhalis growth 2 Target ID: Moraxella catarrhalis growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/11367873	Inhibitor 8504
Streptococcus pneumoniae growth 20 Target ID: Streptococcus pneumoniae growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/11367873	Inhibitor 8504
Haemophilus influenzae growth 4 Target ID: Haemophilus influenzae growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/11367873	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Respiratory tract infections 85 Sources: http://www.mims.com/thailand/drug/info/urfamycin	Curative	Approved 8583	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 8583	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 8583	Urfamycin Approved Use GUT, hepatobiliary, resp tract, enteric tract infections, typhoid, paratyphoid fever & salmonellosis, brucellosis.

C_max

Value	Dose	Analyte	Population
26.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
38.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
66.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	1500 mg single, intravenous dose: 1500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
30.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
53.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
78.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	1500 mg single, intravenous dose: 1500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
18.58 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
29.56 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	THIAMPHENICOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
849.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1305.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2315.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	1500 mg single, intravenous dose: 1500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4509 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
7506.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
12613.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	1500 mg single, intravenous dose: 1500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
234.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4114.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	THIAMPHENICOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
17.6 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
16.8 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
16.8 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	1500 mg single, intravenous dose: 1500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
20.7 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24597465/	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	THIAMPHENICOL AMINOACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
80% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7394975/			THIAMPHENICOL unknown	Homo sapiens

Doses

Dose	Population	Adverse events
2 g single, intraperineal Highest studied dose Dose: 2 g Route: intraperineal Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/7394975/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7394975/	Sources: https://pubmed.ncbi.nlm.nih.gov/7394975/
631 mg 2 times / day multiple, respiratory Studied dose Dose: 631 mg, 2 times / day Route: respiratory Route: multiple Dose: 631 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12120883/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12120883/	Disc. AE: Asthma, Nausea... AEs leading to discontinuation/dose reduction: Asthma (1.1%) Nausea (3.4%) Vomiting (3.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/12120883/

AEs

AE	Significance	Dose	Population
Asthma	1.1% Disc. AE	631 mg 2 times / day multiple, respiratory Studied dose Dose: 631 mg, 2 times / day Route: respiratory Route: multiple Dose: 631 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12120883/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12120883/
Nausea	3.4% Disc. AE	631 mg 2 times / day multiple, respiratory Studied dose Dose: 631 mg, 2 times / day Route: respiratory Route: multiple Dose: 631 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12120883/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12120883/
Vomiting	3.4% Disc. AE	631 mg 2 times / day multiple, respiratory Studied dose Dose: 631 mg, 2 times / day Route: respiratory Route: multiple Dose: 631 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12120883/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12120883/

PubMed

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

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

Name

Type

Language

THIAMPHENICOL AMINOACETATE

Common Name

English

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

Preferred Name

English

THIOPHENICOL GLYCINATE

Common Name

English

Thiamphenicol aminoacetate [WHO-DD]

Common Name

English

THIAMPHENICOL GLYCINE ESTER

Common Name

English

THIAMPHENICOL GLYCINATE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID7048326