THIAMPHENICOL GLYCINATE ACETYLCYSTEINE

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

Structure Search

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

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 180 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22849268	Inhibitor 8504		2.3 µM [Kd]
Bacterial 70S ribosome 180 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22849268	Inhibitor 8504		2.3 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4586141	Curative		Not Provided 511	Unknown Approved Use Unknown
Bacterial infections 235 Sources: http://www.zambon.com.br/media/1145/glitisol-_c%C3%A1psula.pdf	Curative		Approved 8583	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.

C_max

Value	Dose	Analyte	Population
8.3 μg/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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	Analyte	Population
30.1 μg × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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

T_1/2

Value	Dose	Analyte	Population
2.1 h REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
90% REVIEW https://pubmed.ncbi.nlm.nih.gov/6523312/			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: https://pubmed.ncbi.nlm.nih.gov/6240785/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6240785/	Sources: https://pubmed.ncbi.nlm.nih.gov/6240785/
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: https://pubmed.ncbi.nlm.nih.gov/6523326/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6523326/	Sources: https://pubmed.ncbi.nlm.nih.gov/6523326/

PubMed

Title	Date	PubMed
Simultaneous analysis of thiamphenicol and its prodrug thiamphenicol glycinate in human plasma and urine by high performance liquid chromatography: application to pharmacokinetic study.	2006-06-07	16522362
Pharmacokinetics of florfenicol in pigs following intravenous, intramuscular or oral administration and the effects of feed intake on oral dosing.	2006-04	16515670
Determination of florfenicol in fish feed by liquid chromatography.	2006-03-11	16526461
Three cases of occupational asthma induced by thiamphenicol: detection of serum-specific IgE.	2006-03	16436155
Placental transfer of antibiotics administered to the mother: a review.	2006-02	16502764
Role of coresistance in the development of resistance to chloramphenicol in Escherichia coli isolated from sick cattle and pigs.	2006-02	16454626
Pharmacokinetics of florfenicol and its metabolite, florfenicol amine, in the Korean catfish (Silurus asotus).	2006-02	16420300
Differential stability of mitochondrial mRNA in HeLa cells.	2006	16389406
Comparative evaluation between capillary electrophoresis and high-performance liquid chromatography for the analysis of florfenicol in plasma.	2005-10-04	16084049
Assessing the effect of a single dose florfenicol treatment in feedlot cattle on the antimicrobial resistance patterns in faecal Escherichia coli.	2005-08-27	16120248
A new mechanism for chloramphenicol, florfenicol and clindamycin resistance: methylation of 23S ribosomal RNA at A2503.	2005-08	16091044
Fusobacterium nucleatum apoptosis-inducing outer membrane protein.	2005-08	16040725
Molecular basis of florfenicol-induced increase in adherence of Staphylococcus aureus strain Newman.	2005-08	15983028
Pharmacokinetics of florfenicol in the red pacu (Piaractus brachypomus) after single dose intramuscular administration.	2005-06	15953207
Plasmid-borne florfenicol resistance in Pasteurella multocida.	2005-05	15814600
Evaluation of the antimicrobial activity of florfenicol against bacteria isolated from bovine and porcine respiratory disease.	2005-03-20	15737475
Effects of some antibiotics on glutathione reductase activities from human erythrocytes in vitro and from rat erythrocytes in vivo.	2005-02	15895687
Molecular evaluation of antibiotic susceptibility of Tropheryma whipplei in axenic medium.	2005-02	15650004
[Analysis of chloramphenicol, thiamphenicol and florfenicol in chicken by high performance liquid chromatography with electrospray ionization mass spectrometry].	2005-01	15881377
Gene cloning and properties of the RND-type multidrug efflux pumps MexPQ-OpmE and MexMN-OprM from Pseudomonas aeruginosa.	2005	16301811
Evaluation of the therapeutic activity of tulathromycin against swine respiratory disease on farms in Europe.	2005	16094567
Comparative efficacy of tulathromycin versus florfenicol and tilmicosin against undifferentiated bovine respiratory disease in feedlot cattle.	2005	16094565
Comparative efficacy of tulathromycin, tilmicosin, and florfenicol in the treatment of bovine respiratory disease in stocker cattle.	2005	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	16094563
Efficacy of tulathromycin in the treatment and prevention of natural outbreaks of bovine respiratory disease in European cattle.	2005	16094560
Resistance pattern and assessment of phenicol agents' minimum inhibitory concentration in multiple drug resistant Chryseobacterium isolates from fish and aquatic habitats.	2005	16033463
Optimization and validation of a micellar electrokinetic chromatographic method for the analysis of florfenicol.	2004-11-15	15522515
Molecular basis of bacterial resistance to chloramphenicol and florfenicol.	2004-11	15539072
In vitro activity of thiamphenicol, erythromycin and fluoroquinolones against Legionella pneumophila.	2004-10	15565921
Pharmacokinetics of florfenicol in North American elk (Cervus elaphus).	2004-10	15500565
Influence of thiamphenicol on the primary functions of human polymorphonuclear leucocytes against Streptococcus pyogenes.	2004-10	15380265
Pharmacokinetics and bioavailability of florfenicol following intravenous, intramuscular and oral administrations in rabbits.	2004-08	15509025
The effect of testosterone propionate supplement on testicular toxicity with thiamphenicol in male Sprague-Dawley rats.	2004-08	15467268
Effects of subinhibitory concentrations of florfenicol on morphology, growth, and viability of Staphylococcus aureus.	2004-08	15458493
Intravenous and subcutaneous pharmacokinetics of florfenicol in sheep.	2004-08	15305846
Monitoring of florfenicol susceptibility among bovine and porcine respiratory tract pathogens collected in Germany during the years 2002 and 2003.	2004-08	15254030
Characterization of florfenicol resistance among calf pathogenic Escherichia coli.	2004-07-15	15251195
[Construction of SW480 cell model identifying Shigella virulent genes].	2004-07	15640048
Subinhibitory concentrations of florfenicol enhance the adherence of florfenicol-susceptible and florfenicol-resistant Staphylococcus aureus.	2004-07	15175268
Bioavailability and pharmacokinetics of florfenicol in healthy sheep.	2004-06	15189302
Use of florfenicol in non-human primates.	2004-06	15102069
Rickettsia felis, Bartonella henselae, and B. clarridgeiae, New Zealand.	2004-05	15216855
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.	2004-04-15	15063500
Gonorrhoea surveillance system in France: 1986-2000.	2004-04	15028933
Molecular analysis of florfenicol-resistant Escherichia coli isolates from pigs.	2004-01	14645321
[Role of thiamphenicol in the treatment of community-acquired lung infections].	2004	15224555
In vitro effects of some antibiotics on glutathione reductase from sheep liver.	2003-12	15008519
In vitro evaluation of the susceptibility of Edwardsiella ictaluri, etiological agent of enteric septicemia in channel catfish, Ictalurus punctatus (Rafinesque), to florfenicol.	2003-11	14667023
Effects of florfenicol injection on the meat characteristics of the cervical muscles in cattle.	2002-01	16206782
Effect of racephenicol on antibiotic resistance of lactose-fermenting enteric bacteria in chickens.	1973-09	4586141

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

L-CYSTEINE, N-ACETYL-, COMPD. WITH GLYCINE (2R,3R)-2-((2,2-DICHLOROACETYL)AMINO)-3-HYDROXY-3-(4-(METHYLSULFONYL)PHENYL)PROPYL ESTER (1:1)

Preferred Name

English

THIAMPHENICOL GLYCINATE ACETYLCYSTEINE

Common Name

English

Thiamphenicol glycinate acetylcysteine [WHO-DD]

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

243-572-9