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
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. |
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 |
|
Comparative in vitro activity of thiamphenicol-glycinate and thiamphenicol-glycinate-acetylcysteinate and other antimicrobials against respiratory pathogens. | 2001 |
|
A simple classification method for residual antibiotics using E. coli cells transformed by the calcium chloride method and drug resistance plasmid DNA. | 2001 |
|
Molecular features determining lymphocyte reactivity in allergic contact dermatitis to chloramphenicol and azidamphenicol. | 2001 Jan |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
Antimicrobial susceptibilities of Neisseria gonorrhoeae in Kigali, Rwanda, and trends of resistance between 1986 and 2000. | 2001 Sep |
|
Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995. | 2002 Apr |
|
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 florfenicol injection on the meat characteristics of the cervical muscles in cattle. | 2002 Jan |
|
An open, comparative pilot study of thiamphenicol glycinate hydrochloride vs clarithromycin in the treatment of acute lower respiratory tract infections due to Chlamydia pneumoniae. | 2002 Jun |
|
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 |
|
Chloramphenicol and florfenicol susceptibility of fish-pathogenic bacteria isolated in France: comparison of minimum inhibitory concentration, using recommended provisory standards for fish bacteria. | 2003 |
|
Effect of oral enrofloxacin and florfenicol on pigs experimentally infected with Actinobacillus pleuropneumoniae serotype 1. | 2003 Jun |
|
Bioavailability and pharmacokinetics of florfenicol in broiler chickens. | 2003 Oct |
|
Mobile genes coding for efflux-mediated antimicrobial resistance in Gram-positive and Gram-negative bacteria. | 2003 Sep |
|
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 |
|
In vitro activity of thiamphenicol, erythromycin and fluoroquinolones against Legionella pneumophila. | 2004 Oct |
|
Gene cloning and properties of the RND-type multidrug efflux pumps MexPQ-OpmE and MexMN-OprM from Pseudomonas aeruginosa. | 2005 |
|
A new mechanism for chloramphenicol, florfenicol and clindamycin resistance: methylation of 23S ribosomal RNA at A2503. | 2005 Aug |
|
Effects of some antibiotics on glutathione reductase activities from human erythrocytes in vitro and from rat erythrocytes in vivo. | 2005 Feb |
|
[Analysis of chloramphenicol, thiamphenicol and florfenicol in chicken by high performance liquid chromatography with electrospray ionization mass spectrometry]. | 2005 Jan |
|
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
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
Wed Apr 02 08:28:48 GMT 2025
by
admin
on
Wed Apr 02 08:28:48 GMT 2025
|
Record UNII |
283383NO13
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C258
Created by
admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
847-25-6
Created by
admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
|
PRIMARY | |||
|
CHEMBL315338
Created by
admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
|
PRIMARY | |||
|
100000080305
Created by
admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
|
PRIMARY | |||
|
2546
Created by
admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
|
PRIMARY | |||
|
DTXSID401033713
Created by
admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
|
PRIMARY | |||
|
C61920
Created by
admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
|
PRIMARY | |||
|
283383NO13
Created by
admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
|
PRIMARY | |||
|
SUB10231MIG
Created by
admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
|
PRIMARY | |||
|
m10723
Created by
admin on Wed Apr 02 08:28:48 GMT 2025 , Edited by admin on Wed Apr 02 08:28:48 GMT 2025
|
PRIMARY | Merck Index |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ENANTIOMER -> RACEMATE |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |