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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 C5H9NO3S
Molecular Weight 163.195
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED
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
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7447408

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 2.3 µM [Kd]
Inhibitor
8297
 2.3 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Not Provided
504
Unknown

Approved Use

Unknown
Curative
Approved
8429
GLITISOL

Approved Use

This medication is indicated for the treatment of respiratory, genitourinary, hepatobiliary, surgical, soft tissue, otolaryngological (rhinosinusitis, pharyngitis, laryngitis), typhoid, paratyphoid infections, purulent meningitis, brucellosis, sexually transmitted diseases (gonococcal and non-gonococcal urethritis, donovanose, lymphogranuloma venereum), pelvic inflammatory disease, vulvovaginitis, cervicovaginitis and bacterial vaginosis caused by microorganisms sensitive to thiamphenicol.
PubMed

PubMed

TitleDatePubMed
Effect of racephenicol on antibiotic resistance of lactose-fermenting enteric bacteria in chickens.
1973 Sep
An assessment of chloramphenicol and thiamphenicol in the induction of aplastic anaemia in the BALB/c mouse.
2000 Oct
Inhibition of mitochondrial protein synthesis promotes autonomous regulation of mtDNA expression and generation of a new mitochondrial RNA species.
2001 Apr 13
Haemotoxicity of thiamphenicol in the BALB/c mouse and Wistar Hanover rat.
2002 Dec
Clinical efficacy of florfenicol in the treatment of calf respiratory tract infections.
2002 Feb
Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae.
2002 Jan
Liquid chromatographic determination of florfenicol in the plasma of multiple species of fish.
2002 Nov 15
Pharmacokinetics of florfenicol in healthy and Escherichia coli-infected broiler chickens.
2002 Oct
Rickettsia felis in the United Kingdom.
2003 Aug
Antimicrobial susceptibilities of Neisseria gonorrhoeae strains isolated in Java, Indonesia.
2003 Jan
Effect of oral enrofloxacin and florfenicol on pigs experimentally infected with Actinobacillus pleuropneumoniae serotype 1.
2003 Jun
Pharmacokinetics of florfenicol in loggerhead sea turtles (Caretta caretta) after single intravenous and intramuscular injections.
2003 Mar
In vitro evaluation of the susceptibility of Edwardsiella ictaluri, etiological agent of enteric septicemia in channel catfish, Ictalurus punctatus (Rafinesque), to florfenicol.
2003 Nov
Bioavailability and pharmacokinetics of florfenicol in broiler chickens.
2003 Oct
Comparative plasma pharmacokinetics and tolerance of florfenicol following intramuscular and intravenous administration to camels, sheep and goats.
2003 Sep
Mobile genes coding for efflux-mediated antimicrobial resistance in Gram-positive and Gram-negative bacteria.
2003 Sep
Gonorrhoea surveillance system in France: 1986-2000.
2004 Apr
Pharmacokinetics and bioavailability of florfenicol following intravenous, intramuscular and oral administrations in rabbits.
2004 Aug
The effect of testosterone propionate supplement on testicular toxicity with thiamphenicol in male Sprague-Dawley rats.
2004 Aug
Effects of subinhibitory concentrations of florfenicol on morphology, growth, and viability of Staphylococcus aureus.
2004 Aug
Intravenous and subcutaneous pharmacokinetics of florfenicol in sheep.
2004 Aug
Monitoring of florfenicol susceptibility among bovine and porcine respiratory tract pathogens collected in Germany during the years 2002 and 2003.
2004 Aug
Rickettsia felis, Bartonella henselae, and B. clarridgeiae, New Zealand.
2004 May
Molecular basis of bacterial resistance to chloramphenicol and florfenicol.
2004 Nov
In vitro activity of thiamphenicol, erythromycin and fluoroquinolones against Legionella pneumophila.
2004 Oct
Pharmacokinetics of florfenicol in North American elk (Cervus elaphus).
2004 Oct
Influence of thiamphenicol on the primary functions of human polymorphonuclear leucocytes against Streptococcus pyogenes.
2004 Oct
Resistance pattern and assessment of phenicol agents' minimum inhibitory concentration in multiple drug resistant Chryseobacterium isolates from fish and aquatic habitats.
2005
A new mechanism for chloramphenicol, florfenicol and clindamycin resistance: methylation of 23S ribosomal RNA at A2503.
2005 Aug
Molecular basis of florfenicol-induced increase in adherence of Staphylococcus aureus strain Newman.
2005 Aug
Pharmacokinetics of florfenicol in the red pacu (Piaractus brachypomus) after single dose intramuscular administration.
2005 Jun
Evaluation of the antimicrobial activity of florfenicol against bacteria isolated from bovine and porcine respiratory disease.
2005 Mar 20
Determination of florfenicol in fish feed by liquid chromatography.
2005 Nov-Dec
Comparative evaluation between capillary electrophoresis and high-performance liquid chromatography for the analysis of florfenicol in plasma.
2005 Oct 4
Assessing the effect of a single dose florfenicol treatment in feedlot cattle on the antimicrobial resistance patterns in faecal Escherichia coli.
2005 Sep-Dec
Comparative efficacy of tulathromycin versus florfenicol and tilmicosin against undifferentiated bovine respiratory disease in feedlot cattle.
2005 Summer
Pharmacokinetics of florfenicol in pigs following intravenous, intramuscular or oral administration and the effects of feed intake on oral dosing.
2006 Apr
Role of coresistance in the development of resistance to chloramphenicol in Escherichia coli isolated from sick cattle and pigs.
2006 Feb
Simultaneous analysis of thiamphenicol and its prodrug thiamphenicol glycinate in human plasma and urine by high performance liquid chromatography: application to pharmacokinetic study.
2006 Jun 7
Patents

Patents

JPS6379822A
3
WO2004004658
3

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
Created
by admin
on Fri Dec 15 18:47:54 GMT 2023
Edited
by admin
on Fri Dec 15 18:47:54 GMT 2023
Record UNII
7I3XBP3IFP
Record Status Validated (UNII)
Record Version
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Name Type Language
THIAMPHENICOL GLYCINATE ACETYLCYSTEINE
WHO-DD  
Common Name English
L-CYSTEINE, N-ACETYL-, COMPD. WITH GLYCINE (2R,3R)-2-((2,2-DICHLOROACETYL)AMINO)-3-HYDROXY-3-(4-(METHYLSULFONYL)PHENYL)PROPYL ESTER (1:1)
Systematic Name English
Thiamphenicol glycinate acetylcysteine [WHO-DD]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
243-572-9
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
PRIMARY
FDA UNII
7I3XBP3IFP
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
PRIMARY
PUBCHEM
44147002
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
PRIMARY
SMS_ID
100000084824
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
PRIMARY
EVMPD
SUB04804MIG
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID10942260
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
PRIMARY
CAS
20192-91-0
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
PRIMARY
Related Record Type Details
Structure of ACETYLCYSTEINE
PARENT -> SALT/SOLVATE
Structure of THIAMPHENICOL AMINOACETATE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of THIAMPHENICOL
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