darglitazone

{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 451556609

| IUPAC_name = 5-[(4-[3-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)propanoyl]phenyl)methyl]-1,3-thiazolidine-2,4-dione

| image = Darglitazone_structure.svg

| width = 260

| tradename =

| legal_status = Development terminated

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 141200-24-0

| PubChem = 60870

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 55624

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = AVP9C03Z3K

| ChemSpiderID = 54854

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C23H20N2O4S/c1-14-18(24-22(29-14)17-5-3-2-4-6-17)11-12-19(26)16-9-7-15(8-10-16)13-20-21(27)25-23(28)30-20/h2-10,20H,11-13H2,1H3,(H,25,27,28)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = QQKNSPHAFATFNQ-UHFFFAOYSA-N

| C=23 | H=20 | N=2 | O=4 | S=1

| smiles = CC1=C(N=C(O1)C2=CC=CC=C2)CCC(=O)C3=CC=C(C=C3)CC4C(=O)NC(=O)S4

}}

Darglitazone (previously known as CP 86325-2) is a member of the thiazolidinedione class of drugs and an agonist of peroxisome proliferator-activated receptor-γ (PPAR-γ), an orphan member of the nuclear receptor superfamily of transcription factors. It has a variety of insulin-sensitizing effects, such as improving glycemic and lipidemic control, and was researched by Pfizer as a treatment of metabolic disorders such as type 2 diabetes mellitus.{{cite journal | vauthors = Hulin B, Clark DA, Goldstein SW, McDermott RE, Dambek PJ, Kappeler WH, Lamphere CH, Lewis DM, Rizzi JP | display-authors = 6 | title = Novel thiazolidine-2,4-diones as potent euglycemic agents | journal = Journal of Medicinal Chemistry | volume = 35 | issue = 10 | pages = 1853–64 | date = May 1992 | pmid = 1588563 | doi = 10.1021/jm00088a022 }}

Its development was terminated on November 08, 1999.{{cite web |title=Drug Profile: Darglitazone |url=http://adisinsight.springer.com/drugs/800003002| work = Adis Insight |publisher=Springer Nature Switzerland AG |access-date=28 November 2015}}

Darglitazone is a thiazolidinedione, which is a class of drugs that can lower blood sugar without increasing insulin production.

It's an agonist of peroxisome proliferator-activated receptor-γ (PPAR-γ), a transcription factor.

Darglitazone can increase the effectiveness of insulin in people with obesity and type 2 diabetes. [https://pubmed.ncbi.nlm.nih.gov/8582540/ Darglitazone is a thiazolidinedione, which is a class of drugs that can lower blood sugar without increasing insulin production. ]

Synthesis

References

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{{Oral hypoglycemics}}

{{PPAR modulators}}

Category:Abandoned drugs

Category:Oxazoles

Category:Thiazolidinediones