Darglitazone

Names

[ Name ]:
Darglitazone

[Synonym ]:
5-[[4-[3-(5-methyl-2-phenyl-4-oxazolyl)-1-oxopropyl]phenyl]methyl]-2,4-thiazolidinedione
Darglitazone
5-[4-[3-(2-phenyl-5-methyl-4-oxazolyl)propionyl]benzyl]thiazolidine-2,4-dione
5-<4-<3-(5-methyl-2-phenyl-4-oxazolyl)propionyl>-benzyl>thiazolidine-2,4-dione
Darglitazone [INN]
[3H]Darglitazone
5-[4-[3-(5-methyl-2-phenyloxazol-4-yl)propionyl]benzyl]-thiazolidine-2,4-dione
UNII-AVP9C03Z3K

Biological Activity

[Description]:

Darglitazone (CP-86325), a thiazolidinedione, is a potent, selective, and orally active PPAR-γ agonist. Darglitazone is effective in controlling blood glucose and lipid metabolism, and can be used for type II diabetes research[1].

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> PPAR

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

[Target]

PPAR-γ

[In Vitro]

In cell lines representing white (3T3-L1 and 3T3-F442A) and brown (HIB-1B) adipose tissues and skeletal muscle (L6), within 4 h of exposing these cells to 30 μM Darglitazone, there is an increase in uncoupling protein 2 (UCP2) mRNA which reached a plateau of 5-10 times the basal in about 8 h. Darglitazone can stimulate the expression of UCP2 gene probably via PPAR-γ[2].

[In Vivo]

Darglitazone treatment restores euglycemia and normalized elevated corticosterone, triglycerides, and very-low-density lipoprotein levels. Darglitazone dramatically reduces the infarct size in the ob/ob mice at 24 h of recovery. Darglitazone treatment restores acute cerebral inflammatory responses that were absent in the diabetic mice and profoundly improved their recovery from hypoxic-ischemic (H/I) insult[1]. Animal Model: Male diabetic ob/ob mice[1] Dosage: 1 mg/kg Administration: Oral administration; daily; for 7 days Result: Normalized blood glucose and reduced circulating triglycerides (TG) and very-low-density lipoproteins (VLDL) in diabetic ob/ob mice without having any effect in the nondiabetic mice.

[References]

[1]. Rashmi Kumari, et al. The PPAR-gamma agonist, darglitazone, restores acute inflammatory responses to cerebral hypoxia-ischemia in the diabetic ob/ob mouse. J Cereb Blood Flow Metab. 2010 Feb;30(2):352-60.

[2]. A Camirand, et al. Thiazolidinediones stimulate uncoupling protein-2 expression in cell lines representing white and brown adipose tissues and skeletal muscle. Endocrinology. 1998 Jan;139(1):428-31.

Chemical & Physical Properties

[ Molecular Formula ]:
C₂₃H₂₀N₂O₄S

[ Molecular Weight ]:
420.48100

[ Exact Mass ]:
420.11400

[ PSA ]:
118.06000

[ LogP ]:
4.63550

[ Storage condition ]:
-20℃

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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