DENAGLIPTIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H18F3N3O
Molecular Weight	373.3716
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](C(C1=CC=C(F)C=C1)C2=CC=C(F)C=C2)C(=O)N3C[C@@H](F)C[C@H]3C#N

InChI

InChIKey=URRAHSMDPCMOTH-LNLFQRSKSA-N

InChI=1S/C20H18F3N3O/c21-14-5-1-12(2-6-14)18(13-3-7-15(22)8-4-13)19(25)20(27)26-11-16(23)9-17(26)10-24/h1-8,16-19H,9,11,25H2/t16-,17-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H18F3N3O
Molecular Weight	373.3716
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://newdrugapprovals.org/2014/11/25/denagliptin/ | https://www.ncbi.nlm.nih.gov/pubmed/20112433 | https://clinicaltrials.gov/ct2/show/NCT00387972 | https://adisinsight.springer.com/drugs/800020028

Denagliptin is a dipeptidyl peptidase IV (DPP-IV) and and tripeptidyl-peptidase inhibitor, which entered phase III clinical trials in 2006 for the treatment of type 2 diabetes mellitus at GlaxoSmithKline. Development of this compound was put on hold due to unfavorable preliminary data from preclinical long-term toxicity trials. Stress testing or forced degradation studies of denagliptin revealed that drug was stable in the solid-state, but degraded in solution, in blends with all excipients, and in capsules predominantly by cyclization to (3S,7S,8aS) amidine, which epimerized to (3S,7S,8aR) amidine.

Approval Year

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:32:30 GMT 2025` Edited by `admin` on `Mon Mar 31 18:32:30 GMT 2025`
Record UNII	DOS9ZOT21L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DENAGLIPTIN

Official Name

English

Denagliptin [WHO-DD]

Preferred Name

English

denagliptin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98086