RACEPHENICOL

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H15Cl2NO5S
Molecular Weight	356.222
Optical Activity	( + / - )
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](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

HIDE SMILES / InChI

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22849268	Inhibitor 8297		2.3 µM [Kd]
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22849268	Inhibitor 8297		2.3 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4586141	Curative		Not Provided 504	Unknown Approved Use Unknown
Bacterial infections 234 Sources: http://www.zambon.com.br/media/1145/glitisol-_c%C3%A1psula.pdf	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

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
In vitro effects of some antibiotics on glutathione reductase from sheep liver.	2003 Dec	15008519
In vitro evaluation of the susceptibility of Edwardsiella ictaluri, etiological agent of enteric septicemia in channel catfish, Ictalurus punctatus (Rafinesque), to florfenicol.	2003 Nov	14667023
[Role of thiamphenicol in the treatment of community-acquired lung infections].	2004	15224555
Gonorrhoea surveillance system in France: 1986-2000.	2004 Apr	15028933
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	15063500
Pharmacokinetics and bioavailability of florfenicol following intravenous, intramuscular and oral administrations in rabbits.	2004 Aug	15509025
The effect of testosterone propionate supplement on testicular toxicity with thiamphenicol in male Sprague-Dawley rats.	2004 Aug	15467268
Effects of subinhibitory concentrations of florfenicol on morphology, growth, and viability of Staphylococcus aureus.	2004 Aug	15458493
Intravenous and subcutaneous pharmacokinetics of florfenicol in sheep.	2004 Aug	15305846
Monitoring of florfenicol susceptibility among bovine and porcine respiratory tract pathogens collected in Germany during the years 2002 and 2003.	2004 Aug	15254030
Molecular analysis of florfenicol-resistant Escherichia coli isolates from pigs.	2004 Jan	14645321
[Construction of SW480 cell model identifying Shigella virulent genes].	2004 Jul	15640048
Subinhibitory concentrations of florfenicol enhance the adherence of florfenicol-susceptible and florfenicol-resistant Staphylococcus aureus.	2004 Jul	15175268
Characterization of florfenicol resistance among calf pathogenic Escherichia coli.	2004 Jul 15	15251195
Bioavailability and pharmacokinetics of florfenicol in healthy sheep.	2004 Jun	15189302
Use of florfenicol in non-human primates.	2004 Jun	15102069
Rickettsia felis, Bartonella henselae, and B. clarridgeiae, New Zealand.	2004 May	15216855
Molecular basis of bacterial resistance to chloramphenicol and florfenicol.	2004 Nov	15539072
Optimization and validation of a micellar electrokinetic chromatographic method for the analysis of florfenicol.	2004 Nov 15	15522515
In vitro activity of thiamphenicol, erythromycin and fluoroquinolones against Legionella pneumophila.	2004 Oct	15565921
Pharmacokinetics of florfenicol in North American elk (Cervus elaphus).	2004 Oct	15500565
Influence of thiamphenicol on the primary functions of human polymorphonuclear leucocytes against Streptococcus pyogenes.	2004 Oct	15380265
Gene cloning and properties of the RND-type multidrug efflux pumps MexPQ-OpmE and MexMN-OprM from Pseudomonas aeruginosa.	2005	16301811
Resistance pattern and assessment of phenicol agents' minimum inhibitory concentration in multiple drug resistant Chryseobacterium isolates from fish and aquatic habitats.	2005	16033463
A new mechanism for chloramphenicol, florfenicol and clindamycin resistance: methylation of 23S ribosomal RNA at A2503.	2005 Aug	16091044
Fusobacterium nucleatum apoptosis-inducing outer membrane protein.	2005 Aug	16040725
Molecular basis of florfenicol-induced increase in adherence of Staphylococcus aureus strain Newman.	2005 Aug	15983028
Effects of some antibiotics on glutathione reductase activities from human erythrocytes in vitro and from rat erythrocytes in vivo.	2005 Feb	15895687
Molecular evaluation of antibiotic susceptibility of Tropheryma whipplei in axenic medium.	2005 Feb	15650004
[Analysis of chloramphenicol, thiamphenicol and florfenicol in chicken by high performance liquid chromatography with electrospray ionization mass spectrometry].	2005 Jan	15881377
Pharmacokinetics of florfenicol in the red pacu (Piaractus brachypomus) after single dose intramuscular administration.	2005 Jun	15953207
Evaluation of the antimicrobial activity of florfenicol against bacteria isolated from bovine and porcine respiratory disease.	2005 Mar 20	15737475
Plasmid-borne florfenicol resistance in Pasteurella multocida.	2005 May	15814600
Determination of florfenicol in fish feed by liquid chromatography.	2005 Nov-Dec	16526461
Comparative evaluation between capillary electrophoresis and high-performance liquid chromatography for the analysis of florfenicol in plasma.	2005 Oct 4	16084049
Assessing the effect of a single dose florfenicol treatment in feedlot cattle on the antimicrobial resistance patterns in faecal Escherichia coli.	2005 Sep-Dec	16120248
Evaluation of the therapeutic activity of tulathromycin against swine respiratory disease on farms in Europe.	2005 Summer	16094567
Comparative efficacy of tulathromycin versus florfenicol and tilmicosin against undifferentiated bovine respiratory disease in feedlot cattle.	2005 Summer	16094565
Comparative efficacy of tulathromycin, tilmicosin, and florfenicol in the treatment of bovine respiratory disease in stocker cattle.	2005 Summer	16094564
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	16094563
Efficacy of tulathromycin in the treatment and prevention of natural outbreaks of bovine respiratory disease in European cattle.	2005 Summer	16094560
Differential stability of mitochondrial mRNA in HeLa cells.	2006	16389406
Pharmacokinetics of florfenicol in pigs following intravenous, intramuscular or oral administration and the effects of feed intake on oral dosing.	2006 Apr	16515670
Placental transfer of antibiotics administered to the mother: a review.	2006 Feb	16502764
Role of coresistance in the development of resistance to chloramphenicol in Escherichia coli isolated from sick cattle and pigs.	2006 Feb	16454626
Pharmacokinetics of florfenicol and its metabolite, florfenicol amine, in the Korean catfish (Silurus asotus).	2006 Feb	16420300
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	16522362
Three cases of occupational asthma induced by thiamphenicol: detection of serum-specific IgE.	2006 Mar	16436155

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).

Name

Type

Language

RACEPHENICOL

Official Name

English

RACEOPHENIDOL

Common Name

English

(±)-THIAMPHENICOL

Common Name

English

DEXAWIN

Brand Name

English

racefenicol [INN]

Common Name

English

RACEPHENICOL [USAN]

Common Name

English

THIAMPHENICOL DL-FORM

Common Name

English

RACEFENICOL

Official Name

English

THIAMPHENICOL DL-FORM [MI]

Common Name

English

WIN-5063

Code

English

WIN 5063

Code

English

ACETAMIDE, 2,2-DICHLORO-N-(.BETA.-HYDROXY-.ALPHA.-(HYDROXYMETHYL)-P-(METHYLSULFONYL)PHENETHYL)-, THREO-(±)-

Common Name

English

ACETAMIDE, 2,2-DICHLORO-N-(2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-(METHYLSULFONYL)PHENYL)ETHYL)-, (R*,R*)-(±)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258