Vildagliptin 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 insliin 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. Structure
Structure for HMDB15596 (Vildagliptin)
Synonyms
Value Source NVP-LAF237ChEMBL EQUAHMDB GalvusHMDB JalraHMDB LAF 237HMDB LAF237HMDB NVP-LAF-237HMDB XiliarxHMDB (2S)-(((3-Hydroxyadamantan-1-yl)amino)acetyl)pyrrolidine-2-carbonitrileMeSH
Chemical Formlia
C17H25N3O2 Average Molecliar Weight
303.3993 Monoisotopic Molecliar Weight
303.194677059 IUPAC Name
(2S)-1-{2-[(3-hydroxyadamantan-1-yl)amino]acetyl}pyrrolidine-2-carbonitrile Traditional Name
EQUA CAS Registry Number
274901-16-5 SMILES
InChI Identifier
InChI Key
SYOKIDBDQMKNDQ-XWTIBIIYSA-N Chemical Taxonomy Description
This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. Kingdom
Organic compounds Super Class
Organic acids and derivatives Class
Carboxylic acids and derivatives Sub Class
Amino acids, peptides, and analogues Direct Parent
Alpha amino acid amides Alternative Parents
Substituents
Molecliar Framework
Aliphatic heteropolycyclic compounds External Descriptors
Not Available Ontology Status
Expected but not Quantified Origin
Biofunction
Application
Cellliar locations
Physical Properties State
Solid Experimental Properties
Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.75e+00 g/LNot Available LogPNot AvailableNot Available
Predicted Properties
Property Value Source Water Solubility1.75 mg/mLALOGPS logP1.12ALOGPS logP-0.22ChemAxon logS-2.2ALOGPS pKa (Strongest Acidic)14.71ChemAxon pKa (Strongest Basic)9.03ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area76.36 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity82 m3·mol-1ChemAxon Polarizability33.17 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon
Spectra Spectra
Spectrum Type Description Splash Key LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0udi-0109000000-f6f13525e0841cb9a0ceView in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0udi-0902000000-39449b9fce86086b9f42View in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0udi-0900000000-e42a57f8c41f08f0fe2bView in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0udi-0900000000-bdf96b3bb5758ccb2ee2View in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0ue9-0900000000-813cd0c1f6616a3aac1aView in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0udi-0309000000-4cc7261ec4a8a5eb3c50View in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0udi-0901000000-2828160e08a306467998View in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0udi-5900000000-797e5126c08d2be98d02View in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0f6t-9600000000-55a58d88d2018c5adff8View in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0002-9200000000-b511fd9b2243cdaf69ccView in MoNA LC-MS/MS
LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0005-9100000000-5c5cb1119f70d6852572View in MoNA LC-MS/MS
LC-MS/MS Spectrum – , positivesplash10-0udi-1709000000-d62dc38a0bb019fd4bedView in MoNA Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
Biological Properties Cellliar Locations
Biofluid Locations
Tissue Location
Not Available Pathways
Not Available Normal Concentrations
Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04876details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04876
details
Abnormal Concentrations
Not Available Associated Disorders and Diseases Disease References
None Associated OMIM IDs
None External Links DrugBank ID
DB04876 DrugBank Metabolite ID
Not Available Phenol Explorer Compound ID
Not Available Phenol Explorer Metabolite ID
Not Available FoodDB ID
Not Available KNApSAcK ID
Not Available Chemspider ID
5293734 KEGG Compound ID
Not Available BioCyc ID
Not Available BiGG ID
Not Available Wikipedia Link
Vildagliptin NuGOwiki Link
HMDB15596 Metagene Link
HMDB15596 METLIN ID
Not Available PubChem Compound
6918537 PDB ID
Not Available ChEBI ID
334541
References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References- Balas B, Baig MR, Watson C, Dunning BE, Ligueros-Saylan M, Wang Y, He YL, Darland C, Holst JJ, Deacon CF, Cusi K, Mari A, Foley JE, DeFronzo RA: 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. 2007 Apr;92(4):1249-55. Epub 2007 Jan 23. [PubMed:17244786 ]
Enzymes
- General function:
- Involved in serine-type endopeptidase activity
- Specific function:
- Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation. Acts as a positive regulator of T-cell coactivation, by binding at least ADA, CAV1, IGF2R, and PTPRC. Its binding to CAV1 and CARD11 induces T-cell proliferation and NF- kappa-B activation in a T-cell receptor/CD3-dependent manner. Its interaction with ADA also regulates lymphocyte-epithelial cell adhesion. In association with FAP is involved in the pericellular proteolysis of the extracellular matrix (ECM), the migration and invasion of endothelial cells into the ECM. May be involved in the promotion of lymphatic endothelial cells adhesion, migration and tube formation. When overexpressed, enhanced cell proliferation, a process inhibited by GPC3. Acts also as a serine exopeptidase with a dipeptidyl peptidase activity that regulates various physiological processes by cleaving peptides in the circulation, including many chemokines, mitogenic growth factors, neuropeptides and peptide hormones. Removes N-terminal dipeptides sequentially from polypeptides having unsubstituted N-termini provided that the penultimate residue is proline
- Gene Name:
- DPP4
- Uniprot ID:
- P27487
- Molecular weight:
- 88277.9
References
- Ahren B, Gomis R, Standl E, Mills D, Schweizer A: Twelve- and 52-week efficacy of the dipeptidyl peptidase IV inhibitor LAF237 in metformin-treated patients with type 2 diabetes. Diabetes Care. 2004 Dec;27(12):2874-80. [PubMed:15562200 ]
- Mentlein R, Gallwitz B, Schmidt WE: Dipeptidyl-peptidase IV hydrolyses gastric inhibitory polypeptide, glucagon-like peptide-1(7-36)amide, peptide histidine methionine and is responsible for their degradation in human serum. Eur J Biochem. 1993 Jun 15;214(3):829-35. [PubMed:8100523 ]
- Gupta R, Walunj SS, Tokala RK, Parsa KV, Singh SK, Pal M: Emerging drug candidates of dipeptidyl peptidase IV (DPP IV) inhibitor class for the treatment of Type 2 Diabetes. Curr Drug Targets. 2009 Jan;10(1):71-87. [PubMed:19149538 ]