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
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
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 |
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 |
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. |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.3 μg/mL |
0.5 g single, intramuscular dose: 0.5 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5.6 μg/mL |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
32.3 μg/mL |
1.5 g single, intramuscular dose: 1.5 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
17.6 μg/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5.6 μg/mL |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5.9 μg/mL |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
18.6 μg/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
16.7 μg/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
17.6 μg/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
16.1 μg/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
17.8 μg/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30.1 μg × h/mL |
0.5 g single, intravenous dose: 0.5 g route of administration: Intravenous experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
34 μg × h/mL |
0.5 g single, intramuscular dose: 0.5 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
29.4 μg × h/mL |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
117.1 μg × h/mL |
1.5 g single, intramuscular dose: 1.5 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
167.3 μg × h/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
29.4 μg × h/mL |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
28.8 μg × h/mL |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
149.1 μg × h/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
167.3 μg × h/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
158.9 μg × h/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
178.6 μg × h/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
171.6 μg × h/mL |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.1 h |
0.5 g single, intravenous dose: 0.5 g route of administration: Intravenous experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.8 h |
0.5 g single, intramuscular dose: 0.5 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.7 h |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3.2 h |
1.5 g single, intramuscular dose: 1.5 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6.1 h |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.7 h |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.6 h |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5.1 h |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6.1 h |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6 h |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.3 h |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6.9 h |
2.5 g single, oral dose: 2.5 g route of administration: Oral experiment type: SINGLE co-administered: |
THIAMPHENICOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
90% |
THIAMPHENICOL serum | Homo sapiens |
||
100% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/624692/ |
THIAMPHENICOL plasma | Homo sapiens |
Doses
Dose | Population | Adverse events |
---|---|---|
2.5 g 1 times / day multiple, oral Recommended Dose: 2.5 g, 1 times / day Route: oral Route: multiple Dose: 2.5 g, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
|
500 mg 3 times / day multiple, oral Recommended Dose: 500 mg, 3 times / day Route: oral Route: multiple Dose: 500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of racephenicol on antibiotic resistance of lactose-fermenting enteric bacteria in chickens. | 1973 Sep |
|
Inhibition of mitochondrial protein synthesis promotes autonomous regulation of mtDNA expression and generation of a new mitochondrial RNA species. | 2001 Apr 13 |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
The effects of certain antibiotics on biogas production in the anaerobic digestion of pig waste slurry. | 2002 Apr |
|
Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995. | 2002 Apr |
|
Pharmacokinetics of thiamphenicol in pigs. | 2002 Dec |
|
A comparative kinetic study of thiamphenicol in pre-ruminant lambs and calves. | 2002 Dec |
|
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 |
|
Residue depletion of thiamphenicol in the sea-bass. | 2002 Feb |
|
Effects of vaccination prior to transit and administration of florfenicol at time of arrival in a feedlot on the health of transported calves and detection of Mannheimia haemolytica in nasal secretions. | 2002 Feb |
|
Effects of florfenicol injection on the meat characteristics of the cervical muscles in cattle. | 2002 Jan |
|
Molecular analysis of chromosomally florfenicol-resistant Escherichia coli isolates from France and Germany. | 2002 Jan |
|
Pyrrole analogues of chloramphenicol. III. Synthesis and antibacterial activity of DL-threo-1-(1-methylsulfonylpyrrole-3-yl)-2-dichloroacetamidopropane-1,3-diol. | 2002 Mar-Apr |
|
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 |
|
Antimicrobial susceptibilities of Neisseria gonorrhoeae strains isolated in Java, Indonesia. | 2003 Jan |
|
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 |
|
Subinhibitory concentrations of florfenicol enhance the adherence of florfenicol-susceptible and florfenicol-resistant Staphylococcus aureus. | 2004 Jul |
|
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 |
|
Molecular evaluation of antibiotic susceptibility of Tropheryma whipplei in axenic medium. | 2005 Feb |
|
Determination of florfenicol in fish feed by liquid chromatography. | 2005 Nov-Dec |
|
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 |
|
Differential stability of mitochondrial mRNA in HeLa cells. | 2006 |
|
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 |
|
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
Mon Mar 31 19:21:19 GMT 2025
by
admin
on
Mon Mar 31 19:21:19 GMT 2025
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Record UNII |
7I3XBP3IFP
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Record Status |
Validated (UNII)
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Record Version |
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7I3XBP3IFP
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44147002
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100000084824
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SUB04804MIG
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DTXSID10942260
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20192-91-0
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