Danuglipron

Chemical compound

Investigational

Identifiers

IUPAC name

2-[[4-[6-[(4-Cyano-2-fluorophenyl)methoxy]pyridin-2-yl]piperidin-1-yl]methyl]-3-[[(2S)-oxetan-2-yl]methyl]benzimidazole-5-carboxylic acid

CAS Number

2230198-02-2

PubChem CID

134611040

UNII

DN9IUI24GP

ChEMBL

ChEMBL4518483

CompTox Dashboard (EPA)

DTXSID601101457

Chemical and physical dataFormulaC₃₁H₃₀FN₅O₄Molar mass555.610 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

C1CO[C@@H]1CN2C3=C(C=CC(=C3)C(=O)O)N=C2CN4CCC(CC4)C5=NC(=CC=C5)OCC6=C(C=C(C=C6)C#N)F

InChI

InChI=1S/C31H30FN5O4/c32-25-14-20(16-33)4-5-23(25)19-41-30-3-1-2-26(35-30)21-8-11-36(12-9-21)18-29-34-27-7-6-22(31(38)39)15-28(27)37(29)17-24-10-13-40-24/h1-7,14-15,21,24H,8-13,17-19H2,(H,38,39)/t24-/m0/s1
Key:HYBAKUMPISVZQP-DEOSSOPVSA-N

Danuglipron is a small-molecule GLP-1 agonist developed by Pfizer^[1] that, in an oral formulation, is under investigation as a therapy for diabetes mellitus. Initial results from a randomized controlled trial indicate that it reduced weight and improved diabetic control. The most commonly reported adverse events were nausea, diarrhea, and vomiting.^[2]^[3]

References

^ Griffith DA, Edmonds DJ, Fortin JP, Kalgutkar AS, Kuzmiski JB, Loria PM, et al. (June 2022). "A Small-Molecule Oral Agonist of the Human Glucagon-like Peptide-1 Receptor". Journal of Medicinal Chemistry. 65 (12): 8208–8226. doi:10.1021/acs.jmedchem.1c01856. PMC 9234956. PMID 35647711.
^ Saxena AR, Frias JP, Brown LS, Gorman DN, Vasas S, Tsamandouras N, Birnbaum MJ (May 2023). "Efficacy and Safety of Oral Small Molecule Glucagon-Like Peptide 1 Receptor Agonist Danuglipron for Glycemic Control Among Patients With Type 2 Diabetes: A Randomized Clinical Trial". JAMA Network Open. 6 (5): e2314493. doi:10.1001/jamanetworkopen.2023.14493. PMC 10203889. PMID 37213102.
^ Constantino, Annika Kim (2023-12-02). "Pfizer's twice-daily weight loss pill joins a long list of obesity drug flops". CNBC. Retrieved 2023-12-03.

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^‡Withdrawn from market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	1st generation: Acetohexamide Carbutamide Chlorpropamide Glycyclamide Metahexamide Tolazamide Tolbutamide 2nd generation: Glibenclamide (glyburide) Glibornuride Glicaramide Gliclazide^# Glimepiride Glipizide Gliquidone Glisoxepide Glyclopyramide
Meglitinides/"glinides"	Mitiglinide Nateglinide Repaglinide

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