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

SMILES

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

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

Description

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	Inhibitor 8,504		2.22 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262	Primary		Approved 8,583	Marizev

C_max

Value	Dose	Analyte	Population
549 nM	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
523 nM	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
141.51 nM	5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
749.54 nM	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
2709.59 nM	100 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
297.84 nM	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
1712.32 nM	50 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
223.03 nM	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
15.66 nM	1 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
21.25 nM	1 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
236.65 nM	10 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
278.21 nM	10 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
802.6 nM	25 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
700.63 nM	25 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
1083.59 nM	50 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
1305.97 nM	50 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
6.45 nM	0.5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
20.7 nM	1.5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
88.2 nM	5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
219 nM	12.5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
484 nM	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
904 nM	50 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
2210 nM	100 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
3850 nM	200 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
9290 nM	400 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
206 nM	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
195 nM	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
184 nM	10 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
195 nM	10 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
610 nM	25 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
565 nM	25 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
988 nM	50 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
1080 nM	50 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
2320 nM	100 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
2400 nM	100 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
60.4 nM	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
61.4 nM	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
48.7 nM	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
41.4 nM	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
41 nM	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
56.1 nM	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
572 nM	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
554 nM	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
22.7 μM × h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
23 μM × h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
5.34 μM × h	5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
23.81 μM × h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
94.63 μM × h	100 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
9.07 μM × h	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
48.66 μM × h	50 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
8.75 μM × h	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
1.03 μM × h	1 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
1.4 μM × h	1 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
8.92 μM × h	10 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
9.75 μM × h	10 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
21.19 μM × h	25 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
22.31 μM × h	25 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
40.32 μM × h	50 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
41.56 μM × h	50 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
0.147 μM × h	0.5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
1.2 μM × h	1.5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
4.13 μM × h	5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
10.6 μM × h	12.5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
20.9 μM × h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
39.4 μM × h	50 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
82.5 μM × h	100 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
155 μM × h	200 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
323 μM × h	400 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
9.59 μM × h	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
9.99 μM × h	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
7.37 μM × h	10 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
8.76 μM × h	10 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
22 μM × h	25 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
22 μM × h	25 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
40.7 μM × h	50 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
47.8 μM × h	50 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
82.3 μM × h	100 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
87.8 μM × h	100 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
3055 nM × h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
3675 nM × h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
3580 nM × h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
3352 nM × h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
3151 nM × h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
2432 nM × h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
22.4 μM × h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
23.8 μM × h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
46.8 h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
46 h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
66.65 h	5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
38.89 h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
43.41 h	100 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
49.91 h	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
33.43 h	50 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
89.45 h	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
144.88 h	1 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
143.52 h	10 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
82.48 h	25 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
73.73 h	50 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
93.3 h	1.5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
115.94 h	5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
68.88 h	12.5 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
49.52 h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
47.65 h	50 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
42.62 h	100 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
45.19 h	200 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
42.45 h	400 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
119.59 h	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
98.22 h	10 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
83.18 h	10 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
66.74 h	25 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
48.3 h	50 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
41.74 h	100 mg 1 times / week multiple, oral	OMARIGLIPTIN plasma	Homo sapiens
148 h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
156 h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
160 h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
215 h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
264 h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
163 h	3 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
34.6 h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens
34.5 h	25 mg single, oral	OMARIGLIPTIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
24%			OMARIGLIPTIN plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
100 mg 1 times / week multiple, oral Highest studied dose	healthy, ADULT	Other AEs: Headache, Dizziness...
400 mg single, oral Highest studied dose	healthy, ADULT	Other AEs: Headache, Dry mouth...

Showing 1 to 2 of 2 entries

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AEs

Show entries

AE	Dose	Population
Diarrhea	100 mg 1 times / week multiple, oral Highest studied dose	healthy, ADULT
Dizziness postural	100 mg 1 times / week multiple, oral Highest studied dose	healthy, ADULT
Dizziness	100 mg 1 times / week multiple, oral Highest studied dose	healthy, ADULT
Head discomfort	100 mg 1 times / week multiple, oral Highest studied dose	healthy, ADULT
Headache	100 mg 1 times / week multiple, oral Highest studied dose	healthy, ADULT

Showing 1 to 5 of 10 entries

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PubMed

Title	Date	PubMed
No data available in table

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.

Show entries

Name

Type

Language

MK-3102

Preferred Name

English

OMARIGLIPTIN

Official Name

English

OMARIGLIPTIN [USAN]

Common Name

English

omarigliptin [INN]

Common Name

English

OMARIGLIPTIN [MI]

Common Name

English

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Show entries

Code System

Code

Type

Description

USAN

YY-120

PRIMARY

SMS_ID

100000161201

PRIMARY

WIKIPEDIA

Omarigliptin

PRIMARY

INN

9586

PRIMARY

EPA CompTox

DTXSID70153678

PRIMARY

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ACTIVE MOIETY


					CVP59Q4JE1

OMARIGLIPTIN

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound