OMARIGLIPTIN

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H20F2N4O3S
Molecular Weight	398.428
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(=O)(=O)N1C=C2CN(CC2=N1)[C@H]3CO[C@@H]([C@@H](N)C3)C4=CC(F)=CC=C4F

InChI

InChIKey=MKMPWKUAHLTIBJ-ISTRZQFTSA-N

InChI=1S/C17H20F2N4O3S/c1-27(24,25)23-7-10-6-22(8-16(10)21-23)12-5-15(20)17(26-9-12)13-4-11(18)2-3-14(13)19/h2-4,7,12,15,17H,5-6,8-9,20H2,1H3/t12-,15+,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C17H20F2N4O3S
Molecular Weight	398.428
Charge	0
Count

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

Description
Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=36234 | https://www.ncbi.nlm.nih.gov/pubmed/27372109 | https://www.ncbi.nlm.nih.gov/pubmed/26507988

Omarigliptin is a new once-weekly dipeptidyl peptidase-4 (DPP-4) inhibitor developed for the treatment of type 2 diabetes. It potently but reversibly inhibits DPP-4 enzyme, which prolongs the circulating half-life of glucagon-like peptide-1 that increases insulin secretion in a glucose-dependent manner. Benefiting from glucose-dependent insulin secretion, omarigliptin is associated with low risk of hypoglycemia. Marizev (omarigliptin) 25 mg and 12.5 mg tablets were approved by Japan's Pharmaceuticals and Medical Devices Agency (PMDA) on 28th Sept 2015. Japan was the first country to have approved omarigliptin.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dipeptidyl peptidase IV 37 Target ID: CHEMBL284 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27396490 \| https://www.ncbi.nlm.nih.gov/pubmed/24660890	Inhibitor 8297		2.22 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=36234 https://clinicaltrials.gov/ct2/show/NCT01697592 http://adisinsight.springer.com/drugs/800031846	Primary		Approved 8429	Marizev Approved Use Marizev is used to treat type 2 diabetes. Launch Date 2015

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

For adults, take 2 tablets (25 mg of the active ingredient) at a time, once a week. If you are a patient with severe or end stage renal dysfunction, take 1 tablet (12.5 mg) at a time, once a week.

Route of Administration: Oral

In Vitro Use Guide

Omarigliptin is a competitive, reversible inhibitor of DPP-4 (IC50 = 1.6 nM, Ki = 0.8 nM) and is more potent than sitagliptin (IC50 = 18 nM). It is highly selective over all proteases tested (IC50 > 67 uM), including QPP, FAP, PEP, DPP8, and DPP9. The compound has weak ion channel activity (IC50 > 30 uM at IKr, Cav1.2, and Nav1.5). An expansive selectivity counterscreen (168 radioligand binding or enzymatic assays) was carried out at MDS Pharma. An IC50 > 10 uM was obtained in all assays.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:40:30 GMT 2023` Edited by `admin` on `Sat Dec 16 01:40:30 GMT 2023`
Record UNII	CVP59Q4JE1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OMARIGLIPTIN

Official Name

English

OMARIGLIPTIN [USAN]

Common Name

English

omarigliptin [INN]

Common Name

English

OMARIGLIPTIN [MI]

Common Name

English

2H-PYRAN-3-AMINE, 2-(2,5-DIFLUOROPHENYL)-5-(2,6-DIHYDRO-2-(METHYLSULFONYL)PYRROLO(3,4-C)PYRAZOL-5(4H)-YL)TETRAHYDRO-,(2R,3S,5R)-

Common Name

English

OMARIGLIPTIN [JAN]

Common Name

English

MK-3102

Code

English

Omarigliptin [WHO-DD]

Common Name

English

Code System Code Type Description

USAN

YY-120