U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C11H8ClNO2S
Molecular Weight 253.705
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FENCLOZIC ACID

SMILES

OC(=O)CC1=CSC(=N1)C2=CC=C(Cl)C=C2

InChI

InChIKey=APBSKHYXXKHJFK-UHFFFAOYSA-N
InChI=1S/C11H8ClNO2S/c12-8-3-1-7(2-4-8)11-13-9(6-16-11)5-10(14)15/h1-4,6H,5H2,(H,14,15)

HIDE SMILES / InChI

Molecular Formula C11H8ClNO2S
Molecular Weight 253.705
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Fenclozic acid emerged in the late 1960s as a promising carboxylic acid non-steroidal anti-inflammatory drug candidate that demonstrated potent anti-inflammatory, anti-pyretic and analgesic properties. Whole body autoradiography showed fenclozic acid distribution into all tissues except the brain, with radioactivity still detectable in blood, kidney and liver at 72 h post-dose. Fenclozic acid was compared with aspirin in a double-blind, crossover trial in patients with rheumatoid arthritis. It was concluded that fenclozic acid afforded symptomatic relief and was comparable to aspirin. Unfortunately, hepatotoxicity was observed in subsequent trials and the drug was withdrawn from the clinic.

CNS Activity

Curator's Comment: Known to be CNS Non-penetrant in mouse. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
In vitro exploration of potential mechanisms of toxicity of the human hepatotoxic drug fenclozic acid.
2013 Aug
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.
2014 Jan
Acute liver effects, disposition and metabolic fate of [(14)C]-fenclozic acid following oral administration to normal and bile-cannulated male C57BL/6J mice.
2017 Jul
Patents

Sample Use Guides

200, 300 or 400 mg daily for a period of 10 days
Route of Administration: Oral
Partial inhibition of the activities of the biliary efflux transporters BSEP and Mrp2 activities was observed, this was evident only at very high concentrations of fenclozic acid (apparent IC50 ≥ 1,000 uM).
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:07:05 UTC 2023
Edited
by admin
on Sat Dec 16 17:07:05 UTC 2023
Record UNII
58SRQ4DV53
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FENCLOZIC ACID
INN   MI  
INN  
Official Name English
FENCLOZIC ACID [MI]
Common Name English
I.C.I. 54,450
Code English
fenclozic acid [INN]
Common Name English
2-(P-CHLOROPHENYL)-4-THIAZOLEACETIC ACID
Common Name English
ICI-54450
Code English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C65645
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY
PUBCHEM
28858
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY
MESH
C100273
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY
WIKIPEDIA
FENCLOZIC ACID
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY
FDA UNII
58SRQ4DV53
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY
SMS_ID
100000081269
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY
INN
2703
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY
CAS
17969-20-9
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY
EVMPD
SUB07553MIG
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY
MERCK INDEX
m5271
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID4046157
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY
ChEMBL
CHEMBL1909282
Created by admin on Sat Dec 16 17:07:05 UTC 2023 , Edited by admin on Sat Dec 16 17:07:05 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY