CAS 274901-16-5|Vildagliptin (LAF-237)

Introduction：Basic information about CAS 274901-16-5|Vildagliptin (LAF-237), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Vildagliptin (LAF-237) BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Customs
6. Synonyms

Common Name	Vildagliptin (LAF-237)
CAS Number	274901-16-5	Molecular Weight	303.39900
Density	1.27 g/cm3	Boiling Point	531.3ºC at 760 mmHg
Molecular Formula	C₁₇H₂₅N₃O₂	Melting Point	153-155?C
MSDS	/	Flash Point	275.1ºC

Names

Name	Vildagliptin
Synonym	More Synonyms

Vildagliptin (LAF-237) BiologicalActivity

Description	Vildagliptin (LAF-237; NVP-LAF 237) inhibits DPP-4 with IC50 of 2.3 nM.IC50 Value: 2.3 nM[1]Target: DPP-4in vitro: Vildagliptin is an N-substituted glycyl-2-cyanopyrrolidine (figure 2). It is a potent competitive and reversible inhibitor of human and rodent DPP-4 in vitro, with a median inhibitory concentration (IC50) ~2-3 nmol/L. Importantly, vildagliptin inhibits DPP-4 with high specificity relative to other similar peptidases where its IC50 exceeds 200 mol/L [1].in vivo: Compared to age-, gender-, BMI-matched subjects with normal renal function, the mean AUC of vildagliptin after 14 days in patients with mild, moderate, and severe RI increased by 40%, 71%, and 100%, respectively [2]. The treatment was effective in modulating stress in pancreatic tissue, both by reducing levels of stress markers as well as by increasing activity of SOD and catalase. After analyzing the pancreatic histology, we found that vildagliptin was also able to preserve islets and pancreatic β-cells, especially at the concentration of 5 mg/kg [3].Clinical trial: FDA approved drug.
Related Catalog	Signaling Pathways >>Metabolic Enzyme/Protease >>Dipeptidyl PeptidaseResearch Areas >>Metabolic Disease
References	[1]. Villhauer EB, Brinkman JA, Naderi GB et al. 1-[[(3-hydroxy-1-adamantyl) amino]acetyl]-2-cyano-(S)-pyrrolidine: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties. J Med Chem 2003;46:2774-89. [2]. He YL, Kulmatycki K, Zhang Y, Pharmacokinetics of vildagliptin in patients with varying degrees of renal impairment. Int J Clin Pharmacol Ther. 2013 Jun 19. [3]. Avila Dde L, Araújo GR, Silva M, Vildagliptin ameliorates oxidative stress and pancreatic beta cell destruction in type 1 diabetic rats. Arch Med Res. 2013 Apr;44(3):194-202. [4]. Qin CJ, et al. Inhibition of dipeptidyl peptidase IV prevents high fat diet-induced liver cancer angiogenesis by downregulating chemokine ligand 2. Cancer Lett. 2018 Jan 31;420:26-37.

Description

Vildagliptin (LAF-237; NVP-LAF 237) inhibits DPP-4 with IC50 of 2.3 nM.IC50 Value: 2.3 nM[1]Target: DPP-4in vitro: Vildagliptin is an N-substituted glycyl-2-cyanopyrrolidine (figure 2). It is a potent competitive and reversible inhibitor of human and rodent DPP-4 in vitro, with a median inhibitory concentration (IC50) ~2-3 nmol/L. Importantly, vildagliptin inhibits DPP-4 with high specificity relative to other similar peptidases where its IC50 exceeds 200 mol/L [1].in vivo: Compared to age-, gender-, BMI-matched subjects with normal renal function, the mean AUC of vildagliptin after 14 days in patients with mild, moderate, and severe RI increased by 40%, 71%, and 100%, respectively [2]. The treatment was effective in modulating stress in pancreatic tissue, both by reducing levels of stress markers as well as by increasing activity of SOD and catalase. After analyzing the pancreatic histology, we found that vildagliptin was also able to preserve islets and pancreatic β-cells, especially at the concentration of 5 mg/kg [3].Clinical trial: FDA approved drug.

Related Catalog

Signaling Pathways >>Metabolic Enzyme/Protease >>Dipeptidyl PeptidaseResearch Areas >>Metabolic Disease

References

[1]. Villhauer EB, Brinkman JA, Naderi GB et al. 1-[[(3-hydroxy-1-adamantyl) amino]acetyl]-2-cyano-(S)-pyrrolidine: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties. J Med Chem 2003;46:2774-89.

[2]. He YL, Kulmatycki K, Zhang Y, Pharmacokinetics of vildagliptin in patients with varying degrees of renal impairment. Int J Clin Pharmacol Ther. 2013 Jun 19.

[3]. Avila Dde L, Araújo GR, Silva M, Vildagliptin ameliorates oxidative stress and pancreatic beta cell destruction in type 1 diabetic rats. Arch Med Res. 2013 Apr;44(3):194-202.

[4]. Qin CJ, et al. Inhibition of dipeptidyl peptidase IV prevents high fat diet-induced liver cancer angiogenesis by downregulating chemokine ligand 2. Cancer Lett. 2018 Jan 31;420:26-37.

Chemical & Physical Properties

Density	1.27 g/cm3
Boiling Point	531.3ºC at 760 mmHg
Melting Point	153-155?C
Molecular Formula	C₁₇H₂₅N₃O₂
Molecular Weight	303.39900
Flash Point	275.1ºC
Exact Mass	303.19500
PSA	76.36000
LogP	1.50308
InChIKey	SYOKIDBDQMKNDQ-XWTIBIIYSA-N
SMILES	N#CC1CCCN1C(=O)CNC12CC3CC(CC(O)(C3)C1)C2
Storage condition	-20°C Freezer

Safety Information

Hazard Codes	Xi
HS Code	2933990090

Customs

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Synonyms

2-Pyrrolidinecarbonitrile, 1-[2-[(3-hydroxytricyclo[3.3.1.1]dec-1-yl)amino]acetyl]-, (2S)-

Galvus

(-)-(2S)-1-[[(3-Hydroxytricyclo[3.3.1.1[3,7]]dec-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile

Vildagliptin

Laf 237

(2S)-1-[N-(3-Hydroxyadamantan-1-yl)glycyl]pyrrolidine-2-carbonitrile

(2S)-1-[N-(3-hydroxytricyclo[3.3.1.1]dec-1-yl)glycyl]pyrrolidine-2-carbonitrile

Unii-I6B4B2U96p

(2S)-1-[N-(3-Hydroxyadamantan-1-yl)glycyl]-2-pyrrolidinecarbonitrile

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