Vildagliptin

Bezeichnung:Vildagliptin

CAS-Nr274901-16-5

Englisch Name:Vildagliptin

CBNumberCB71449010

SummenformelC17H25N3O2

Molgewicht303.4

MOL-Datei274901-16-5.mol

Vildagliptin physikalisch-chemischer Eigenschaften

Schmelzpunkt	153-155?C
alpha	-78.3° (c = 9.73 in methanol)
Siedepunkt	531.3±50.0 °C(Predicted)
Dichte	1.27
Flammpunkt	275.1℃
storage temp.	Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
Löslichkeit	Soluble in DMSO (up to 45 mg/ml), in DMF (up to 20 mg/ml), or in Ethanol (up to 20 mg/ml).
Aggregatzustand	solid
pka	15.05±0.40(Predicted)
Farbe	White
Stabilität	Stable for 2 years from date of purchase as supplied. Solutions in DMSO, DMF, or ethanol may be stored at -20°C for up to 3 months
InChI	InChI=1S/C17H25N3O2/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/t12?,13?,14-,16?,17?/m0/s1
InChIKey	SYOKIDBDQMKNDQ-XWTIBIIYSA-N
SMILES	N1(C(CNC23CC4CC(CC(O)(C4)C2)C3)=O)CCC[C@H]1C#N
CAS Datenbank	274901-16-5(CAS DataBase Reference)

Sicherheit

R-Sätze:	28-38-41-48
S-Sätze:	24/25-26-28-36/37/39
RIDADR	3077
HS Code	29339900

Gefahreninformationscode (GHS)

Vildagliptin Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Vildagliptin, a DPP-4 inhibitor, was launched for the oral treatment of type 2 diabetes. Vildagliptin is the second DPP-4 inhibitor to reach the market behind sitagliptin, which was introduced in 2006. DPP-4 inhibitors act by slowing the inactivation of incretins, which are endogenous peptides involved in the physiologic regulation of glucose homeostasis. When blood glucose concentrations are normal or elevated, GLP-1 and GIP increase the synthesis and release of insulin from pancreatic βcells via intracellular signaling pathways involving cAMP. GLP-1 also lowers glucagon secretion from pancreatic α cells, which leads to reduced hepatic glucose production. However, although GLP-1 and GIP effectively lower blood glucose, they are short-lived as a result of rapid inactivation by the ubiquitous serine protease DPP-4. By inhibiting DPP-4, vildagliptin increases the concentration and duration of active incretin levels, which in turn results in increased insulin release and decreased glucagon levels in a glucose-dependent manner. Both vildagliptin and sitagliptin are potent, competitive, reversible inhibitors of DPP- 4 (IC₅₀=3.5 and 18 nM, respectively), and they both show slow, tight-binding inhibition kinetics.
Chemische Eigenschaften
White Solid
Originator
Novartis (US)
Verwenden
The major metabolite of Vildagliptin
Verwenden
A metabolite of Vildagliptin
Verwenden
Vildagliptin (LAF-237) inhibits DPP?4 with IC50 of 2.3 nM
Verwenden
Labelled Vildagliptin. It is a new oral anti-hyperglycemic agent of a new dipeptidyl peptidase-IV (DPP-IV) inhibitor class of drugs. Antidiabetic.
Definition
ChEBI: Vildagliptin is an amino acid amide.
Trademarks
Galvus
Clinical Use
Dipeptidyl peptidase 4 inhibitor:
Treatment of type 2 diabetes mellitus in combination with other antidiabetic drugs
Nebenwirkungen
The most common adverse events reported in patients receiving vildagliptin included headache, nasopharyngitis, cough, constipation, dizziness, and increased sweating. Vildagliptin is not recommended for patients with liver impairment.
Synthese
Vildagliptin is chemically derived in three steps starting from L-prolinamide via acylation with chloroacetyl chloride to produce 1-(chloroacetyl)-L-prolinamide, subsequent dehydration of the carboxamide group to the nitrile with trifluoroacetic anhydride, and condensation of the 1-(chloroacetyl)-L-prolinenitrile intermediate with 3-hydroxyadamantan-1-amine.
target
DDP-4
Stoffwechsel
About 69
% of a dose of vildagliptin is metabolised, mainly by hydrolysis in the kidney to inactive metabolites. About 85
% of a dose is excreted in the urine (23
% as unchanged drug), and 15
% in the faeces.
Einzelnachweise
1) Balas?et al.?(2007),?The dipeptidyl peptidase IV inhibitor vildagliptin suppresses endogenous glucose production and enhances islet function after single-dose administration in type 2 diabetic patients;? J. Clin. Endocrinol. Metab.,?92?1249 2) Ahren?et al. (2004),?Inhibition of dipeptidyl peptidase-4 reduces glycemia, sustains insulin levels and reduces glucagon levels in type 2 diabetes;? J. Clin. Endocrinol. Metab., 89?2078 3) Kosaraju?et al. (2013),?Vildagliptin: an anti-diabetes agent ameliorates cognitive deficits and pathology observed in streptozotocin-induced Alzheimer’s disease;? J. Pharm. Pharmacol.,?65?1773 4) Shimizu?et al. (2012),?DPP4 inhibitor vildagliptin preserves? β-cell mass through amelioration of endoplasmic reticulum stress in C/EBPB transgenic mice;? J. Mol. Endocrinol.,?49?125

Vildagliptin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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