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Details

Stereochemistry RACEMIC
Molecular Formula C19H17ClF3NO4
Molecular Weight 415.791
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HALOFENATE

SMILES

CC(=O)NCCOC(=O)C(OC1=CC=CC(=C1)C(F)(F)F)C2=CC=C(Cl)C=C2

InChI

InChIKey=BJBCSGQLZQGGIQ-UHFFFAOYSA-N
InChI=1S/C19H17ClF3NO4/c1-12(25)24-9-10-27-18(26)17(13-5-7-15(20)8-6-13)28-16-4-2-3-14(11-16)19(21,22)23/h2-8,11,17H,9-10H2,1H3,(H,24,25)

HIDE SMILES / InChI

Molecular Formula C19H17ClF3NO4
Molecular Weight 415.791
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Halofenate (MK-185) was invented as a hypolipidemic and hypouricemic agent. It was shown that halofenate lower serum triglycerides and uric acid in patients with a variety of hyperlipidemias. Treatment of dyslipidemic type 2 diabetic patients also showed triglyceride lowering and, surprisingly, significant reductions in plasma glucose and insulin. Halofenate is a selective PPAR-γ modulator (SPPARγM). SPPARγMs are believed to bind in distinct manners to the ligand-binding pocket of PPAR-γ, leading to altered receptor conformational stability and resulting in distinct patterns of gene expression. Thus, was suggested that halofenate hold promising therapeutic potential in the treatment of type 2 diabetes, without the side effects. However, information about the current use of this compound is not available.

Approval Year

PubMed

PubMed

TitleDatePubMed
Hypolipidemic, uricosuric, and thyroxine-displacing effects of MK-185 (halofenate).
1971 May-Jun
Effect of halofenate and clofibrate on lipid synthesis in rat adipocytes.
1975 Feb 20
Halofenate. Its selection and trial as a primary uricosuric agent.
1975 Nov-Dec
The effect of halofenate or halofenate free acid on human, rat and guinea pig platelet aggregation.
1976 Apr 30
Rational design of a pirinixic acid derivative that acts as subtype-selective PPARgamma modulator.
2010 Apr 15
Patents

Patents

Sample Use Guides

Combined halofenate-chlorpropamide was evaluated for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). Four subjects treated with 500 mg/day chlorpropamide were given 500-1000 mg halofenate daily for 48 wk or longer.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:17:29 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:29 GMT 2023
Record UNII
K9TZK4MNO6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HALOFENATE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
MK-185
Code English
BENZENEACETIC ACID, 4-CHLORO-.ALPHA.-(3-(TRIFLUOROMETHYL)PHENOXY)-, 2-(ACETYLAMINO)ETHYL ESTER
Common Name English
HALOFENATE [USAN]
Common Name English
(P-CHLOROPHENYL)((.ALPHA.,.ALPHA.,.ALPHA-TRIFLUORO-M-TOLYL)OXY)ACETIC ACID ESTER WITH N-(2-HYDROXYETHYL)ACETAMIDE
Common Name English
ACETAMIDE, N-(2-HYDROXYETHYL)-, (P-CHLOROPHENYL)((.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-M-TOLYL)OXY)ACETATE (ESTER)
Common Name English
Halofenate [WHO-DD]
Common Name English
ACETIC ACID, (P-CHLOROPHENYL)((.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-M-TOLYL)OXY)-, ESTER WITH N-(2-HYDROXYETHYL)ACETAMIDE
Systematic Name English
halofenate [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C921
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
NCI_THESAURUS C29703
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
Code System Code Type Description
INN
2536
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
PRIMARY
FDA UNII
K9TZK4MNO6
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
PRIMARY
CAS
24091-96-1
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
SUPERSEDED
EVMPD
SUB07999MIG
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL456071
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
PRIMARY
NCI_THESAURUS
C83805
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
PRIMARY
PUBCHEM
33584
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
PRIMARY
MESH
D006218
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID9023120
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
PRIMARY
SMS_ID
100000083922
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
PRIMARY
CAS
26718-25-2
Created by admin on Fri Dec 15 15:17:29 GMT 2023 , Edited by admin on Fri Dec 15 15:17:29 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE