Vildagliptin

HCID 6918537CAS 274901-16-5

Grundinformationen

Standard-SMILES
N#C[C@@H]1CCCN1C(=O)CNC12CC3CC(CC(O)(C3)C1)C2
InChIKey
SYOKIDBDQMKNDQ-XWTIBIIYSA-N
Summenformel
C17H25N3O2
Durchschnittliche Molmasse
303,4 g/mol

Überblick

Vildagliptin is an amino acid amide.

Namen und Bezeichner

Bevorzugter Name
Vildagliptin
IUPAC
(2S)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile

Namen und Synonyme

VildagliptinGalvus274901-16-5NVP-LAF237EquaLAF237LAF-237VitagliptinNVP-LAF 237(2S)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrilevildagliptineVildagliptina
Weitere Namen anzeigen
I6B4B2U96P(2S)-(((3-hydroxyadamantan-1-yl)amino)acetyl)pyrrolidine-2-carbonitrileDTXSID80881091vildagliptinumNVP LAF237(2S)-1-(2-((3-hydroxy-1-adamantyl)amino)acetyl)pyrrolidine-2-carbonitrileRefChem:6349(2S)-{((3-Hydroxyadamantan-1-yl)amino)acetyl}pyrrolidine-2-carbonitrile

Datenbank-Bezeichner

CAS
274901-16-5
PubChem CID
6918537
ChEMBL
CHEMBL142703
ChEBI
CHEBI:135285
UNII
I6B4B2U96P
EC Number
630-410-0

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,9
Polarare Oberfläche (TPSA)
76,4 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
3
Schwere Atome
22

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Used in Switzerland
Solubility1.75e+00 g/L
Human Drugs · 3 Einträge

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

Physical DescriptionSolid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

This chemical does not meet GHS hazard criteria for 1.4% (1 of 71) of reports.

H413 (90.1%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 71 reports by companies from 10 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesAquatic Chronic 4 (90.1%)

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

A10BH02

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Protein BindingThe plasma protein binding of vildagliptin is 9.3%. Vildagliptin distributes equally between plasma and red blood cells.
Pharmacodynamics · 1 Eintrag

Vildagliptin works to improve glycemic control in type II diabetes mellitus by enhancing the glucose sensitivity of beta-cells (β-cells) in pancreatic islets and promoting glucose-dependent insulin secretion. Increased GLP-1 levels leads to enhanced sensitivity of alpha cells to glucose, promoting glucagon secretion. Vildagliptin causes an increase in the insulin to glucagon ratio by increasing incretin hormone levels: this results in a decrease in fasting and postprandial hepatic glucose production. Vildagliptin does not affect gastric emptying. It also has no effects on insulin secretion or blood glucose levels in individuals with normal glycemic control. In clinical trials, treatment with vildagliptin 50-100 mg daily in patients with type 2 diabetes significantly improved markers of beta-cells, proinsulin to insulin ratio, and measures of beta-cell responsiveness from the frequently-sampled meal tolerance test. Vildagliptin has improves glycated hemoglobin (HbA1c) and fasting plasma glucose (FPG) levels.

Mechanism of Action · 1 Eintrag

Glucagon-like peptide-1 (GLP-1) and glucose-dependent insulinotropic peptide (GIP) are incretin hormones that regulate blood glucose levels and maintain glucose homeostasis. It is estimated that the activity of GLP-1 and GIP contribute more than 70% to the insulin response to an oral glucose challenge. They stimulate insulin secretion in a glucose-dependent manner via G-protein-coupled GIP and GLP-1 receptor signalling. In addition to their effects on insulin secretion, GLP-1 is also involved in promoting islet neogenesis and differentiation, as well as attenuating pancreatic beta-cell apoptosis. Incretin hormones also exert extra-pancreatic effects, such as lipogenesis and myocardial function. In type II diabetes mellitus, GLP-1 secretion is impaired, and the insulinotropic effect of GIP is significantly diminished. Vildagliptin exerts its blood glucose-lowering effects by selectively inhibiting dipeptidyl peptidase-4 (DPP-4), an enzyme that rapidly truncates and inactivates GLP-1 and GIP upon their release from the intestinal cells. DPP-4 cleaves oligopeptides after the second amino acid from the N-terminal end. Inhibition of DPP-4 substantially prolongs the half-life of GLP-1 and GIP, increasing the levels of active circulating incretin hormones. The duration of DPP-4 inhibition by vildagliptin is dose-dependent. Vildagliptin reduces fasting and prandial glucose and HbA1c. It enhances the glucose sensitivity of alpha- and beta-cells and augments glucose-dependent insulin secretion. Fasting and postprandial glucose levels are decreased, and postprandial lipid and lipoprotein metabolism are also improved.

Biological Half-LifeThe mean elimination half-life following intravenous administration is approximately two hours. The elimination half-life after oral administration is approximately three hours.
Metabolism/Metabolites · 1 Eintrag

About 69% of orally administered vildagpliptin is eliminated via metabolism not mediated by cytochrome P450 enzymes. Based on the findings of a rat study, DPP-4 contributes partially to the hydrolysis of vildagliptin. Vildagliptin is metabolized to pharmacologically inactive cyano (57%) and amide (4%) hydrolysis products in the kidney. LAY 151 (M20.7) is a major inactive metabolite and a carboxylic acid that is formed via hydrolysis of the cyano moiety: it accounts for 57% of the dose. Other circulating metabolites reported are an N-glucuronide (M20.2), an N-amide hydrolysis product (M15.3), two oxidation products, M21.6 and M20.9.

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >750

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