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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
Effect of racephenicol on antibiotic resistance of lactose-fermenting enteric bacteria in chickens.
1973 Sep
An assessment of chloramphenicol and thiamphenicol in the induction of aplastic anaemia in the BALB/c mouse.
2000 Oct
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
Antimicrobial activity of thiamphenicol-glycinate-acetylcysteinate and other drugs against Chlamydia pneumoniae.
2001
Inhibition of mitochondrial protein synthesis promotes autonomous regulation of mtDNA expression and generation of a new mitochondrial RNA species.
2001 Apr 13
Molecular features determining lymphocyte reactivity in allergic contact dermatitis to chloramphenicol and azidamphenicol.
2001 Jan
Allometric analysis of thiamphenicol disposition among seven mammalian species.
2001 Jun
Serum soluble transferrin receptor concentration is an accurate estimate of the mass of tissue receptors.
2001 Jun
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Evaluation of certain veterinary drug residues in food.
2002
In vitro activity of thiamphenicol against multiresistant Streptococcus pneumoniae, Haemophilus influenzae and Staphylococcus aureus in Italy.
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
Liquid chromatographic determination of florfenicol in the plasma of multiple species of fish.
2002 Nov 15
Tissue pharmacokinetics of florfenicol in pigs experimentally infected with Actinobacillus pleuropneumoniae.
2002 Oct-Dec
Florfenicol resistance in Salmonella enterica serovar Newport mediated by a plasmid related to R55 from Klebsiella pneumoniae.
2003 Apr
Stability of florfenicol in drinking water.
2003 Jan-Feb
Intravenous and subcutaneous pharmacokinetics of florfenicol in sheep.
2004 Aug
Subinhibitory concentrations of florfenicol enhance the adherence of florfenicol-susceptible and florfenicol-resistant Staphylococcus aureus.
2004 Jul
Use of florfenicol in non-human primates.
2004 Jun
Rickettsia felis, Bartonella henselae, and B. clarridgeiae, New Zealand.
2004 May
Optimization and validation of a micellar electrokinetic chromatographic method for the analysis of florfenicol.
2004 Nov 15
Influence of thiamphenicol on the primary functions of human polymorphonuclear leucocytes against Streptococcus pyogenes.
2004 Oct
A new mechanism for chloramphenicol, florfenicol and clindamycin resistance: methylation of 23S ribosomal RNA at A2503.
2005 Aug
Determination of florfenicol in fish feed by liquid chromatography.
2005 Nov-Dec
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 GMT 2023
Edited
by admin
on Fri Dec 15 18:47:54 GMT 2023
Record UNII
7I3XBP3IFP
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
PRIMARY
FDA UNII
7I3XBP3IFP
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
PRIMARY
PUBCHEM
44147002
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
PRIMARY
SMS_ID
100000084824
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
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EVMPD
SUB04804MIG
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
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EPA CompTox
DTXSID10942260
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 2023
PRIMARY
CAS
20192-91-0
Created by admin on Fri Dec 15 18:47:54 GMT 2023 , Edited by admin on Fri Dec 15 18:47:54 GMT 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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