DENAGLIPTIN TOSYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H18F3N3O.C7H8O3S
Molecular Weight	545.573
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)S(O)(=O)=O.N[C@@H](C(C2=CC=C(F)C=C2)C3=CC=C(F)C=C3)C(=O)N4C[C@@H](F)C[C@H]4C#N

InChI

InChIKey=MSCWUTTUQLYJFT-QMBKNIKNSA-N

InChI=1S/C20H18F3N3O.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h1-8,16-19H,9,11,25H2;2-5H,1H3,(H,8,9,10)/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

Molecular Formula	C7H8O3S
Molecular Weight	172.202
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 `Fri Dec 15 15:29:47 GMT 2023` Edited by `admin` on `Fri Dec 15 15:29:47 GMT 2023`
Record UNII	T47477CUF7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DENAGLIPTIN TOSYLATE

Official Name

English

GW823093C

Code

English

2-PYRROLIDINECARBONITRILE, 1-((2S)-2-AMINO-3,3-BIS(4-FLUOROPHENYL)-1-OXOPROPYL)-4-FLUORO-, (2S,4S)-, MONO(4-METHYLBENZENESULFONATE)

Common Name

English

DENAGLIPTIN TOSILATE

Common Name

English

DENAGLIPTIN TOSYLATE [USAN]

Common Name

English

(2S,4S)-1-[(2S)-2-Amino-3,3-bis(4-fluorophenyl)propanoyl]-4-fluoropyrrolidine-2-carbonitrile 4-methylbenzenesulfonate

Systematic Name

English

GW-823093C

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C98086