Darglitazone: Difference between revisions

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	'''Darglitazone''' (previously known as '''CP 86325-2''') is a member of the ~~{{w\|~~thiazolidinedione}} class of drugs and an agonist of ] (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 ] as a treatment of metabolic disorders such as ~~{{w\|~~Diabetes mellitus type 2\|type 2 diabetes mellitus}}.<ref>{{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 }}</ref>		'''Darglitazone''' (previously known as '''CP 86325-2''') is a member of the ] class of drugs and an agonist of ] (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 ] as a treatment of metabolic disorders such as ].<ref>{{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 }}</ref>

	Its development was terminated on November 08, 1999.<ref>{{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}}</ref>		Its development was terminated on November 08, 1999.<ref>{{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}}</ref>

Latest revision as of 18:17, 8 August 2024

Chemical compound Pharmaceutical compound

Darglitazone
Legal status

Legal status	Development terminated
Identifiers
IUPAC name 5-phenyl)methyl]-1,3-thiazolidine-2,4-dione
CAS Number	141200-24-0
PubChem CID	60870
ChemSpider	54854
UNII	AVP9C03Z3K
ChEMBL	ChEMBL55624
CompTox Dashboard (EPA)	DTXSID3057644
Chemical and physical data
Formula	C₂₃H₂₀N₂O₄S
Molar mass	420.48 g·mol
3D model (JSmol)	Interactive image
SMILES CC1=C(N=C(O1)C2=CC=CC=C2)CCC(=O)C3=CC=C(C=C3)CC4C(=O)NC(=O)S4
InChI InChI=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) Key:QQKNSPHAFATFNQ-UHFFFAOYSA-N
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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.

Its development was terminated on November 08, 1999.

Synthesis

References

Hulin B, Clark DA, Goldstein SW, McDermott RE, Dambek PJ, Kappeler WH, et al. (May 1992). "Novel thiazolidine-2,4-diones as potent euglycemic agents". Journal of Medicinal Chemistry. 35 (10): 1853–64. doi:10.1021/jm00088a022. PMID 1588563.
"Drug Profile: Darglitazone". Adis Insight. Springer Nature Switzerland AG. Retrieved 28 November 2015.

Oral diabetes medication, insulins and insulin analogs, and other drugs used in diabetes (A10)

Insulins / insulin analogs

fast-acting	Insulin aspart Insulin glulisine Insulin lispro
short-acting	Regular insulin
long-acting	Insulin detemir Insulin glargine (+lixisenatide) NPH insulin Lente insulin Ultralente insulin
ultra-long-acting	Insulin degludec (+insulin aspart, +liraglutide) Insulin icodec (+semaglutide)
inhalable	Exubera Afrezza

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Non-insulins

Insulin sensitizers

Biguanides	Buformin Metformin Phenformin
TZDs/"glitazones" (PPAR)	Ciglitazone Darglitazone Englitazone Lobeglitazone Netoglitazone Pioglitazone Rivoglitazone Rosiglitazone Troglitazone
Dual PPAR agonists	Aleglitazar Muraglitazar Saroglitazar Tesaglitazar
Amylin analogs and DACRAs	Cagrilintide Pramlintide

Secretagogues

K_ATP

Sulfonylureas

2nd generation: Glibenclamide (glyburide)
Glibornuride
Glicaramide
Gliclazide
Glimepiride
Glipizide
Gliquidone
Glisoxepide
Glyclopyramide

Meglitinides/"glinides"

GLP-1 receptor agonists

GLP1 poly-agonist peptides	Mazdutide (GLP-1/GCGR) Retatrutide (GLP-1/GIP/GCGR) Tirzepatide (GLP-1/GIP)

DPP-4 inhibitors/"gliptins"

Other

Aldose reductase inhibitors	Epalrestat Fidarestat Ranirestat Tolrestat Zenarestat
Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose
SGLT2 inhibitors/"gliflozins"	Canagliflozin Dapagliflozin Empagliflozin Ertugliflozin Ipragliflozin Luseogliflozin Remogliflozin Sergliflozin Sotagliflozin Tofogliflozin Velagliflozin
Other	Benfluorex Bromocriptine Imeglimin

Combinations

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

v t e PPARTooltip Peroxisome proliferator-activated receptor modulators
PPARαTooltip Peroxisome proliferator-activated receptor alpha	Agonists: 15-HETE 15-HpETE Aleglitazar Aluminium clofibrate Arachidonic acid Bezafibrate Chiglitazar Clofibrate CP-775146 Daidzein DHEA (prasterone) (in rodents) Elafibranor Etomoxir Fenofibrate Genistein Gemfibrozil GW-7647 Lanifibranor Leukotriene B₄ LG-101506 LG-100754 Lobeglitazone Muraglitazar Oleylethanolamide Palmitoylethanolamide Pemafibrate Perfluorononanoic acid Perfluorooctanoic acid Pioglitazone Saroglitazar Sodelglitazar Tesaglitazar Tetradecylthioacetic acid Troglitazone WY-14643 Antagonists: GW-6471 MK-886
PPARδTooltip Peroxisome proliferator-activated receptor delta	Agonists: 15-HETE 15-HpETE Arachidonic acid Bezafibrate Daidzein Elafibranor Fonadelpar Genistein GW-0742 GW-501516 L-165,041 Lanifibranor LG-101506 Seladelpar Sodelglitazar Tetradecylthioacetic acid Antagonists: FH-535 GSK-0660 GSK-3787
PPARγTooltip Peroxisome proliferator-activated receptor gamma	Agonists: 5-Oxo-ETE 5-Oxo-15-hydroxy-ETE 15-Deoxy-Δ-prostaglandin J₂ 15-HETE 15-HpETE Aleglitazar Arachidonic acid Balaglitazone Berberine Bezafibrate Cannabidiol Cevoglitazar Chiglitazar Ciglitazone Daidzein Darglitazone Edaglitazone Efatutazone Englitazone Etalocib Farglitazar Genistein GW-1929 Ibuprofen Imiglitazar Indeglitazar Lanifibranor LG-100268 LG-100754 LG-101506 Lobeglitazone Muraglitazar (muroglitazar) nTZDpa Naveglitazar Netoglitazone Oxeglitazar Peliglitazar Pemaglitazar Perfluorononanoic acid Pioglitazone Prostaglandin J₂ Ragaglitazar Reglitazar Rivoglitazone Rosiglitazone RS5444 Saroglitazar Sipoglitazar Sodelglitazar Telmisartan Tesaglitazar Troglitazone SPPARMsTooltip Selective PPARγ modulator: BADGE EPI-001 INT-131 MK-0533 S26948 Antagonists: FH-535 GW-9662 SR-202 T-0070907 Unknown: SR-1664
Non-selective	Agonists: Ciprofibrate Clinofibrate Clofibride Englitazone Etofibrate Farglitazar Netoglitazone Ronifibrate Rivoglitazone Simfibrate
See also Receptor/signaling modulators

Categories:

Revision as of 12:26, 3 January 2023 editEntranced98 (talk \| contribs)Extended confirmed users, Pending changes reviewers, Rollbackers172,777 edits +sd← Previous edit		Latest revision as of 18:17, 8 August 2024 edit undoAnomieBOT (talk \| contribs)Bots6,568,443 editsm Substing templates: {{W}}. See User:AnomieBOT/docs/TemplateSubster for info.
Line 32:		Line 32:
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	'''Darglitazone''' (previously known as '''CP 86325-2''') is a member of the ~~{{w\|~~thiazolidinedione}} class of drugs and an agonist of ] (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 ] as a treatment of metabolic disorders such as ~~{{w\|~~Diabetes mellitus type 2\|type 2 diabetes mellitus}}.<ref>{{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 }}</ref>		'''Darglitazone''' (previously known as '''CP 86325-2''') is a member of the ] class of drugs and an agonist of ] (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 ] as a treatment of metabolic disorders such as ].<ref>{{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 }}</ref>

	Its development was terminated on November 08, 1999.<ref>{{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}}</ref>		Its development was terminated on November 08, 1999.<ref>{{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}}</ref>