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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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
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
Effects of florfenicol injection on the meat characteristics of the cervical muscles in cattle.
2002 Jan
In vitro effects of some antibiotics on glutathione reductase from sheep liver.
2003 Dec
In vitro evaluation of the susceptibility of Edwardsiella ictaluri, etiological agent of enteric septicemia in channel catfish, Ictalurus punctatus (Rafinesque), to florfenicol.
2003 Nov
[Role of thiamphenicol in the treatment of community-acquired lung infections].
2004
Gonorrhoea surveillance system in France: 1986-2000.
2004 Apr
Plasmid-mediated florfenicol and ceftriaxone resistance encoded by the floR and bla(CMY-2) genes in Salmonella enterica serovars Typhimurium and Newport isolated in the United States.
2004 Apr 15
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
Molecular analysis of florfenicol-resistant Escherichia coli isolates from pigs.
2004 Jan
[Construction of SW480 cell model identifying Shigella virulent genes].
2004 Jul
Subinhibitory concentrations of florfenicol enhance the adherence of florfenicol-susceptible and florfenicol-resistant Staphylococcus aureus.
2004 Jul
Characterization of florfenicol resistance among calf pathogenic Escherichia coli.
2004 Jul 15
Bioavailability and pharmacokinetics of florfenicol in healthy sheep.
2004 Jun
Use of florfenicol in non-human primates.
2004 Jun
Rickettsia felis, Bartonella henselae, and B. clarridgeiae, New Zealand.
2004 May
Molecular basis of bacterial resistance to chloramphenicol and florfenicol.
2004 Nov
Optimization and validation of a micellar electrokinetic chromatographic method for the analysis of florfenicol.
2004 Nov 15
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
Gene cloning and properties of the RND-type multidrug efflux pumps MexPQ-OpmE and MexMN-OprM from Pseudomonas aeruginosa.
2005
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
Fusobacterium nucleatum apoptosis-inducing outer membrane protein.
2005 Aug
Molecular basis of florfenicol-induced increase in adherence of Staphylococcus aureus strain Newman.
2005 Aug
Effects of some antibiotics on glutathione reductase activities from human erythrocytes in vitro and from rat erythrocytes in vivo.
2005 Feb
Molecular evaluation of antibiotic susceptibility of Tropheryma whipplei in axenic medium.
2005 Feb
[Analysis of chloramphenicol, thiamphenicol and florfenicol in chicken by high performance liquid chromatography with electrospray ionization mass spectrometry].
2005 Jan
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
Plasmid-borne florfenicol resistance in Pasteurella multocida.
2005 May
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
Evaluation of the therapeutic activity of tulathromycin against swine respiratory disease on farms in Europe.
2005 Summer
Comparative efficacy of tulathromycin versus florfenicol and tilmicosin against undifferentiated bovine respiratory disease in feedlot cattle.
2005 Summer
Comparative efficacy of tulathromycin, tilmicosin, and florfenicol in the treatment of bovine respiratory disease in stocker cattle.
2005 Summer
Efficacy of tulathromycin compared with tilmicosin and florfenicol for the control of respiratory disease in cattle at high risk of developing bovine respiratory disease.
2005 Summer
Efficacy of tulathromycin in the treatment and prevention of natural outbreaks of bovine respiratory disease in European cattle.
2005 Summer
Differential stability of mitochondrial mRNA in HeLa cells.
2006
Pharmacokinetics of florfenicol in pigs following intravenous, intramuscular or oral administration and the effects of feed intake on oral dosing.
2006 Apr
Placental transfer of antibiotics administered to the mother: a review.
2006 Feb
Role of coresistance in the development of resistance to chloramphenicol in Escherichia coli isolated from sick cattle and pigs.
2006 Feb
Pharmacokinetics of florfenicol and its metabolite, florfenicol amine, in the Korean catfish (Silurus asotus).
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
Three cases of occupational asthma induced by thiamphenicol: detection of serum-specific IgE.
2006 Mar
Patents

Sample Use Guides

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 UTC 2023
Edited
by admin
on Fri Dec 15 18:47:54 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
FDA UNII
7I3XBP3IFP
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
PUBCHEM
44147002
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
SMS_ID
100000084824
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
EVMPD
SUB04804MIG
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID10942260
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
CAS
20192-91-0
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
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