Arhalofenate

Structural formula
General
Non-proprietary name	Arhalofenate
other names	(-) - Halofenate ( R ) -halofenate (2 R ) -2- (4-Chlorophenyl) -2- [3- (trifluoromethyl) phenoxy] acetate-2-acetylaminoethyl ester 2-Acetamidoethyl (2 R ) -2- (4-chlorophenyl) -2- [3- (trifluoromethyl) phenoxy] acetate
Molecular formula	C 19 H 17 ClF 3 NO 4
External identifiers / databases
CAS number 24136-23-0 EC number 689-413-0 ECHA InfoCard 100.216.298 PubChem 12082259 Wikidata Q653074
Drug information
ATC code	A10
Drug class	Antidiabetic drug
Mechanism of action	PPAR γ partial agonist
properties
Molar mass	415,80 g · mol -1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances danger H and P phrases H: 301-319-400 P: 273-301 + 310-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Arhalofenate is a potential drug in clinical development to be used as an anti-diabetic drug in the treatment of type 2 diabetes . Chemically it is the ( R ) - enantiomer of the halofenate . Arhalofenate is a prodrug and as such is only converted into its active form, the free ( R ) - (4-chlorophenyl) - (3-trifluoromethylphenoxy) acetic acid, in the organism .

Active form of arhalofenate

This mediates its effects as a partial agonist via peroxisome proliferator-activated receptors γ (PPARγ). In animal experiments , arhalofenate has been shown to have an insulin sensitizing and blood sugar lowering effect. In addition, arhalofenate lowers the level of triglycerides in the blood through a mechanism that is as yet unknown.

Arhalofenate is being developed by the US pharmaceutical company Metabolex .

Stereochemistry

Arhalofenate is the active ( R ) - enantiomer , the eutomer , of the racemic drug halofenate [1: 1 mixture of ( R ) - and ( S ) -enantiomer] with a stereocenter.

Individual evidence

1. ↑ There is not yet a harmonized classification for this substance . A label of [No public or meaningful name is available] in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 6, 2019, is derived from a self-classification by the distributor .
2. ↑ Data sheet MBX-102 from Sigma-Aldrich , accessed on February 16, 2020 ( PDF ).
3. ↑ Entry on arhalofenate. In: Römpp Online . Georg Thieme Verlag, accessed on December 3, 2019.
4. ^ Gregoire FM, Zhang F, Clarke HJ, et al. : MBX-102 / JNJ39659100, a novel peroxisome proliferator-activated receptor-ligand with weak transactivation activity retains antidiabetic properties in the absence of weight gain and edema . In: Molecular Endocrinology (Baltimore, Md.) . 23, No. 7, July 2009, pp. 975-988. doi : 10.1210 / me.2008-0473 . PMID 19389808 .
5. ↑ Chandalia A, Clarke HJ, Clemens LE et al. : MBX-102 / JNJ39659100, a Novel Non-TZD Selective Partial PPAR-gamma Agonist Lowers Triglyceride Independently of PPAR-alpha Activation . In: PPAR Research . 2009, 2009, p. 706852. doi : 10.1155 / 2009/706852 . PMID 19404482 . PMC 2673481 (free full text).
6. ^ J. Xu: Metabolic Diseases Drug Discovery - Strategic Research Institute's Third International World Summit. PPAR and PTB1B modulators. In: IDrugs. 2004, 7, pp. 836-838.