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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

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
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
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

Description
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 2.3 µM [Kd]
Inhibitor
8297
 2.3 µM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Not Provided
504
Unknown

Approved Use

Unknown
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

PubMed

TitleDatePubMed
A simple classification method for residual antibiotics using E. coli cells transformed by the calcium chloride method and drug resistance plasmid DNA.
2001
Inhibition of mitochondrial protein synthesis promotes autonomous regulation of mtDNA expression and generation of a new mitochondrial RNA species.
2001 Apr 13
Allometric analysis of thiamphenicol disposition among seven mammalian species.
2001 Jun
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995.
2002 Apr
Haemotoxicity of thiamphenicol in the BALB/c mouse and Wistar Hanover rat.
2002 Dec
Residue depletion of thiamphenicol in the sea-bass.
2002 Feb
Liquid chromatographic determination of florfenicol in the plasma of multiple species of fish.
2002 Nov 15
Florfenicol resistance in Salmonella enterica serovar Newport mediated by a plasmid related to R55 from Klebsiella pneumoniae.
2003 Apr
Effect of oral enrofloxacin and florfenicol on pigs experimentally infected with Actinobacillus pleuropneumoniae serotype 1.
2003 Jun
Pharmacokinetics of florfenicol in loggerhead sea turtles (Caretta caretta) after single intravenous and intramuscular injections.
2003 Mar
Safety of Aquaflor (florfenicol, 50% type A medicated article), administered in feed to channel catfish, Ictalurus punctatus.
2003 Nov-Dec
[Role of thiamphenicol in the treatment of community-acquired lung infections].
2004
Pharmacokinetics and bioavailability of florfenicol following intravenous, intramuscular and oral administrations in rabbits.
2004 Aug
Optimization and validation of a micellar electrokinetic chromatographic method for the analysis of florfenicol.
2004 Nov 15
A new mechanism for chloramphenicol, florfenicol and clindamycin resistance: methylation of 23S ribosomal RNA at A2503.
2005 Aug
Fusobacterium nucleatum apoptosis-inducing outer membrane protein.
2005 Aug
Molecular evaluation of antibiotic susceptibility of Tropheryma whipplei in axenic medium.
2005 Feb
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
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
Patents

Patents

JPS6379822A
3
WO2004004658
3

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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:47:54 UTC 2023
Edited
by admin
on Fri Dec 15 18:47:54 UTC 2023
Record UNII
7I3XBP3IFP
Record Status Validated (UNII)
Record Version
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Name Type Language
THIAMPHENICOL GLYCINATE ACETYLCYSTEINE
WHO-DD  
Common Name English
L-CYSTEINE, N-ACETYL-, COMPD. WITH GLYCINE (2R,3R)-2-((2,2-DICHLOROACETYL)AMINO)-3-HYDROXY-3-(4-(METHYLSULFONYL)PHENYL)PROPYL ESTER (1:1)
Systematic Name English
Thiamphenicol glycinate acetylcysteine [WHO-DD]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
243-572-9
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
FDA UNII
7I3XBP3IFP
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
PUBCHEM
44147002
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
SMS_ID
100000084824
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
EVMPD
SUB04804MIG
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID10942260
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
CAS
20192-91-0
Created by admin on Fri Dec 15 18:47:54 UTC 2023 , Edited by admin on Fri Dec 15 18:47:54 UTC 2023
PRIMARY
Related Record Type Details
Structure of ACETYLCYSTEINE
PARENT -> SALT/SOLVATE
Structure of THIAMPHENICOL AMINOACETATE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of THIAMPHENICOL
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