Vildagliptin hydrochloride

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H25N3O2.ClH
Molecular Weight	339.86
Optical Activity	( - )
Defined Stereocenters	1 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

Cl.OC12CC3CC(C1)CC(C3)(C2)NCC(=O)N4CCC[C@H]4C#N

InChI

InChIKey=RZUUYWHYKBKAGN-DNSMMRBLSA-N

InChI=1S/C17H25N3O2.ClH/c18-9-14-2-1-3-20(14)15(21)10-19-16-5-12-4-13(6-16)8-17(22,7-12)11-16;/h12-14,19,22H,1-8,10-11H2;1H/t12?,13?,14-,16?,17?;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Molecular Formula	C17H25N3O2
Molecular Weight	303.3993
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	1 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Vildagliptin, previously identified as LAF237, is a new oral anti-hyperglycemic agent (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. Vildagliptin inhibits the inactivation of GLP-1 and GIP by DPP-4, allowing GLP-1 and GIP to potentiate the secretion of insulin in the beta cells and suppress glucaon release by the alpha cells of the islets of Langerhans in the pancreas. It is currently in clinical trials in the U.S. and has been shown to reduce hyperglycemia in type 2 diabetes mellitus. While the drug is still not approved for use in the US, it was approved in Feb 2008 by European Medicines Agency for use within the EU and is listed on the Australian PBS with certain restrictions. Vildagliptin is marketed under the trade names Galvus, Zomelis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dipeptidyl peptidase IV 37	Inhibitor 8,297		62.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259	Primary		Approved 8,429	Galvus

C_max

Value	Dose	Analyte	Population
162 ng/mL	25 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
272 ng/mL	50 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
671 ng/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
1959 ng/mL	200 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
2860 ng/mL	400 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
524 ng/mL	50 mg 2 times / day multiple, oral	VILDAGLIPTIN plasma	Homo sapiens
415 ng/mL	50 mg 2 times / day multiple, oral	VILDAGLIPTIN plasma	Homo sapiens
538 ng/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
431 ng/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
675 ng/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
497 ng/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
512 ng/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
632 ng/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
545 ng × h/mL	25 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
1139 ng × h/mL	50 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
2968 ng × h/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
6857 ng × h/mL	200 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
13420 ng × h/mL	400 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
1480 ng × h/mL	50 mg 2 times / day multiple, oral	VILDAGLIPTIN plasma	Homo sapiens
1490 ng × h/mL	50 mg 2 times / day multiple, oral	VILDAGLIPTIN plasma	Homo sapiens
2500 ng × h/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
2215 ng × h/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
2567 ng × h/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
2076 ng × h/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
2411 ng × h/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
3322 ng × h/mL	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.54 h	25 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
1.77 h	50 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
2.1 h	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
2 h	200 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
5.29 h	400 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
1.78 h	50 mg 2 times / day multiple, oral	VILDAGLIPTIN plasma	Homo sapiens
2.41 h	50 mg 2 times / day multiple, oral	VILDAGLIPTIN plasma	Homo sapiens
2.1 h	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
2.9 h	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
2 h	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
4.9 h	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
3.1 h	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens
2.4 h	100 mg single, oral	VILDAGLIPTIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
90.7%			VILDAGLIPTIN plasma	Homo sapiens

Doses

Doses

Show entries

Dose	Population	Adverse events
400 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT
100 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT

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PubMed

Show entries

Title	Date	PubMed
New therapeutic strategies for the treatment of type 2 diabetes mellitus based on incretins.	2005 Summer	17491680
The absolute oral bioavailability and population-based pharmacokinetic modelling of a novel dipeptidylpeptidase-IV inhibitor, vildagliptin, in healthy volunteers.	2007	17713976
Pharmacokinetics and pharmacodynamics of vildagliptin in patients with type 2 diabetes mellitus.	2007	17596103
Review of sitagliptin phosphate: a novel treatment for type 2 diabetes.	2007	17580730
11 Years of cyanopyrrolidines as DPP-IV inhibitors.	2007	17352679

Showing 1 to 5 of 50 entries

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Patents

Sample Use Guides

In Vivo Use Guide

When used as monotherapy, in combination with metformin, in combination with thiazolidinedione, in combination with metformin and a sulphonylurea, or in combination with insulin (with or without metformin), the recommended daily dose of vildagliptin is 100 mg, administered as one dose of 50 mg in the morning and one dose of 50 mg in the evening. When used in dual combination with a sulphonylurea, the recommended dose of vildagliptin is 50 mg once daily administered in the morning. In this patient population, vildagliptin 100 mg daily was no more effective than vildagliptin 50 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

Vildagliptin inhibited rat plasma DPP-IV activity in vitro with an IC(50) value of 2.12 nmol/l

Substance Class	Chemical
Record UNII	9KND64V2AA
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

Vildagliptin hydrochloride

Common Name

English

Vildagliptin hydrochloride [WHO-DD]

Common Name

English

2-Pyrrolidinecarbonitrile, 1-[2-[(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-, hydrochloride (1:1), (2S)-

Systematic Name

English

(2S)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile hydrochloride

Systematic Name

English

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Code System

Code

Type

Description

PUBCHEM

16070539

PRIMARY

CAS

924914-75-0

PRIMARY

FDA UNII

9KND64V2AA

PRIMARY

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Related Record

Type

Details


					I6B4B2U96P

Vildagliptin

PARENT -> SALT/SOLVATE

Amount:

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound