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
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)
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 Unfortunately, hepatotoxicity was observed in subsequent trials and the drug was withdrawn from the clinic.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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27896398
Curator's Comment: Known to be CNS Non-penetrant in mouse. Human data not available.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23609606 |
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Target ID: CHEMBL2094253 Sources: http://adisinsight.springer.com/drugs/800000957 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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In vitro exploration of potential mechanisms of toxicity of the human hepatotoxic drug fenclozic acid. | 2013 Aug |
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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 |
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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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4903319
200, 300 or 400 mg daily for a period of 10 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23609606
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
Edited
Sat Dec 16 17:07:05 GMT 2023
by
admin
on
Sat Dec 16 17:07:05 GMT 2023
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Record UNII |
58SRQ4DV53
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C1323
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C65645
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28858
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C100273
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FENCLOZIC ACID
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58SRQ4DV53
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100000081269
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2703
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17969-20-9
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SUB07553MIG
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m5271
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DTXSID4046157
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CHEMBL1909282
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Related Record | Type | Details | ||
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ACTIVE MOIETY |