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
Molecular Formula | C12H15Cl2NO5S |
Molecular Weight | 356.222 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/4586141http://www.zambon.com.br/media/1145/glitisol-_c%C3%A1psula.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22849268Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7447408
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4586141http://www.zambon.com.br/media/1145/glitisol-_c%C3%A1psula.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22849268
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
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015487.pdf
Curator's Comment: Data for L-enantiomer (thiamphenicol)
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22849268 |
2.3 µM [Kd] | ||
Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22849268 |
2.3 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Unknown Approved UseUnknown |
|||
Curative | GLITISOL Approved UseThis 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
Title | Date | PubMed |
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Effect of racephenicol on antibiotic resistance of lactose-fermenting enteric bacteria in chickens. | 1973 Sep |
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Effects of florfenicol injection on the meat characteristics of the cervical muscles in cattle. | 2002 Jan |
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Chloramphenicol and florfenicol susceptibility of fish-pathogenic bacteria isolated in France: comparison of minimum inhibitory concentration, using recommended provisory standards for fish bacteria. | 2003 |
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In vitro effects of some antibiotics on glutathione reductase from sheep liver. | 2003 Dec |
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In vitro evaluation of the susceptibility of Edwardsiella ictaluri, etiological agent of enteric septicemia in channel catfish, Ictalurus punctatus (Rafinesque), to florfenicol. | 2003 Nov |
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Bioavailability and pharmacokinetics of florfenicol in broiler chickens. | 2003 Oct |
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Serogroup A Neisseria meningitidis outside meningitis belt in southwest Cameroon. | 2003 Oct |
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Pharmacokinetics of florfenicol in cod Gadus morhua and in vitro antibacterial activity against Vibrio anguillarum. | 2003 Sep 24 |
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[Role of thiamphenicol in the treatment of community-acquired lung infections]. | 2004 |
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Gonorrhoea surveillance system in France: 1986-2000. | 2004 Apr |
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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 |
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Pharmacokinetics and bioavailability of florfenicol following intravenous, intramuscular and oral administrations in rabbits. | 2004 Aug |
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The effect of testosterone propionate supplement on testicular toxicity with thiamphenicol in male Sprague-Dawley rats. | 2004 Aug |
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Intravenous and subcutaneous pharmacokinetics of florfenicol in sheep. | 2004 Aug |
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Monitoring of florfenicol susceptibility among bovine and porcine respiratory tract pathogens collected in Germany during the years 2002 and 2003. | 2004 Aug |
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Molecular analysis of florfenicol-resistant Escherichia coli isolates from pigs. | 2004 Jan |
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[Construction of SW480 cell model identifying Shigella virulent genes]. | 2004 Jul |
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Subinhibitory concentrations of florfenicol enhance the adherence of florfenicol-susceptible and florfenicol-resistant Staphylococcus aureus. | 2004 Jul |
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Characterization of florfenicol resistance among calf pathogenic Escherichia coli. | 2004 Jul 15 |
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Bioavailability and pharmacokinetics of florfenicol in healthy sheep. | 2004 Jun |
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Use of florfenicol in non-human primates. | 2004 Jun |
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Rickettsia felis, Bartonella henselae, and B. clarridgeiae, New Zealand. | 2004 May |
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Molecular basis of bacterial resistance to chloramphenicol and florfenicol. | 2004 Nov |
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Optimization and validation of a micellar electrokinetic chromatographic method for the analysis of florfenicol. | 2004 Nov 15 |
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In vitro activity of thiamphenicol, erythromycin and fluoroquinolones against Legionella pneumophila. | 2004 Oct |
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Pharmacokinetics of florfenicol in North American elk (Cervus elaphus). | 2004 Oct |
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Influence of thiamphenicol on the primary functions of human polymorphonuclear leucocytes against Streptococcus pyogenes. | 2004 Oct |
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Gene cloning and properties of the RND-type multidrug efflux pumps MexPQ-OpmE and MexMN-OprM from Pseudomonas aeruginosa. | 2005 |
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Resistance pattern and assessment of phenicol agents' minimum inhibitory concentration in multiple drug resistant Chryseobacterium isolates from fish and aquatic habitats. | 2005 |
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A new mechanism for chloramphenicol, florfenicol and clindamycin resistance: methylation of 23S ribosomal RNA at A2503. | 2005 Aug |
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Fusobacterium nucleatum apoptosis-inducing outer membrane protein. | 2005 Aug |
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Molecular basis of florfenicol-induced increase in adherence of Staphylococcus aureus strain Newman. | 2005 Aug |
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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 |
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Pharmacokinetics of florfenicol in the red pacu (Piaractus brachypomus) after single dose intramuscular administration. | 2005 Jun |
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Evaluation of the antimicrobial activity of florfenicol against bacteria isolated from bovine and porcine respiratory disease. | 2005 Mar 20 |
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Plasmid-borne florfenicol resistance in Pasteurella multocida. | 2005 May |
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Determination of florfenicol in fish feed by liquid chromatography. | 2005 Nov-Dec |
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Comparative evaluation between capillary electrophoresis and high-performance liquid chromatography for the analysis of florfenicol in plasma. | 2005 Oct 4 |
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Assessing the effect of a single dose florfenicol treatment in feedlot cattle on the antimicrobial resistance patterns in faecal Escherichia coli. | 2005 Sep-Dec |
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Comparative efficacy of tulathromycin versus florfenicol and tilmicosin against undifferentiated bovine respiratory disease in feedlot cattle. | 2005 Summer |
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Comparative efficacy of tulathromycin, tilmicosin, and florfenicol in the treatment of bovine respiratory disease in stocker cattle. | 2005 Summer |
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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 |
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Efficacy of tulathromycin in the treatment and prevention of natural outbreaks of bovine respiratory disease in European cattle. | 2005 Summer |
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Pharmacokinetics of florfenicol in pigs following intravenous, intramuscular or oral administration and the effects of feed intake on oral dosing. | 2006 Apr |
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Placental transfer of antibiotics administered to the mother: a review. | 2006 Feb |
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Role of coresistance in the development of resistance to chloramphenicol in Escherichia coli isolated from sick cattle and pigs. | 2006 Feb |
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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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4586141
100 or 200 g/ton
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447408
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
Edited
Sat Dec 16 17:18:32 GMT 2023
by
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on
Sat Dec 16 17:18:32 GMT 2023
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Record UNII |
FLQ7571NPM
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Record Status |
Validated (UNII)
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Record Version |
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C258
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