Identification

Name
Vildagliptin
Accession Number
DB04876
Type
Small Molecule
Groups
Approved, Investigational
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.

Structure
Thumb
Synonyms
  • EQUA
  • Galvus
  • Jalra
  • LAF237
  • NVP-LAF-237
  • NVP-LAF237
  • Vildagliptin
  • Xiliarx
External IDs
LAF 237 / LAF-237 / NVP-LAF 237
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
GalvusTablet50 mgOralNovartis Europharm Limited2007-09-26Not applicableEu
GalvusTablet50 mgOralNovartis Europharm Limited2007-09-26Not applicableEu
GalvusTablet50 mgOralNovartis Europharm Limited2007-09-26Not applicableEu
GalvusTablet50 mgOralNovartis Europharm Limited2007-09-26Not applicableEu
GalvusTablet50 mgOralNovartis Europharm Limited2007-09-26Not applicableEu
GalvusTablet50 mgOralNovartis Europharm Limited2007-09-26Not applicableEu
GalvusTablet50 mgOralNovartis Europharm Limited2007-09-26Not applicableEu
GalvusTablet50 mgOralNovartis Europharm Limited2007-09-26Not applicableEu
GalvusTablet50 mgOralNovartis Europharm Limited2007-09-26Not applicableEu
GalvusTablet50 mgOralNovartis Europharm Limited2007-09-26Not applicableEu
International/Other Brands
Galvus
Categories
UNII
I6B4B2U96P
CAS number
274901-16-5
Weight
Average: 303.3993
Monoisotopic: 303.194677059
Chemical Formula
C17H25N3O2
InChI Key
SYOKIDBDQMKNDQ-XWTIBIIYSA-N
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
IUPAC Name
(2S)-1-{2-[(3-hydroxyadamantan-1-yl)amino]acetyl}pyrrolidine-2-carbonitrile
SMILES
OC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[[email protected]]1C#N

Pharmacology

Indication

Used to reduce hyperglycemia in type 2 diabetes mellitus.

Structured Indications
Pharmacodynamics

Vildagliptin belongs to a class of orally active antidiabetic drugs (DPP-IV inhibitors) that appear to have multiple functional benefits beyond simple blood-glucose control. One of these is a potential protective effect on pancreatic beta cells, which deteriorate in diabetes. Vildagliptin appears to be safe, very well tolerated, and efficacious. Following a meal, gut incretin hormones are released. The most important incretin hormones are GLP-1 and glucose-dependent insulinotropic polypeptide (GIP). These hormones, secreted in the human small intestine, are responsible for insulin release due to increased glucose levels. In contrast to agents that promote insulin secretion via glucose-independent mechanisms, GLP-1's dependence on glucose concentration is considered beneficial due to a lower risk of hypoglycemia. GLP-1 also inhibits glucagon secretion and increases beta cell mass by stimulating proliferation and neogenesis. However, the clinical utility of GLP-1 is limited by its short half-life (2 minutes). GLP-1 is rapidly degraded by the proteolytic enzyme DPP-IV. To enhance GLP-1 activity, inhibition of the DPP-IV enzyme is emerging as a novel therapeutic approach in the treatment of diabetes. Administration of vildagliptin enhances GLP-1's ability to produce insulin in response to elevated concentrations of blood glucose, inhibit the release of glucagon following meals, slow the rate of nutrient absorption into the bloodstream, slow the rate of gastric emptying, and reduce food intake.

Mechanism of action

Vildagliptin inhibits dipeptidyl peptidase-4 (DPP-4). This in turn inhibits the inactivation of GLP-1 by DPP-4, allowing GLP-1 to potentiate the secretion of insulin in the beta cells. Dipeptidyl peptidase-4's role in blood glucose regulation is thought to be through degradation of GIP and the degradation of GLP-1.

TargetActionsOrganism
ADipeptidyl peptidase 4
inhibitor
Human
Absorption

Rapidly absorbed following oral administration with an oral bioavailability of greater than 90%.

Volume of distribution
Not Available
Protein binding

9.3%

Metabolism
Not Available
Route of elimination
Not Available
Half life

The elimination half-life is approximately 90 minutes.

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Vildagliptin.Approved, Investigational
AcetohexamideVildagliptin may increase the hypoglycemic activities of Acetohexamide.Investigational, Withdrawn
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Vildagliptin.Approved, Investigational
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Vildagliptin.Approved, Illicit, Investigational
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be decreased when it is combined with Vildagliptin.Experimental, Investigational
AmineptineThe serum concentration of Amineptine can be increased when it is combined with Vildagliptin.Illicit, Withdrawn
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Vildagliptin.Approved
AmoxapineThe serum concentration of Amoxapine can be increased when it is combined with Vildagliptin.Approved
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Vildagliptin.Approved
BenazeprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Benazepril.Approved, Investigational
BendroflumethiazideThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Bendroflumethiazide.Approved
BoceprevirThe serum concentration of Vildagliptin can be decreased when it is combined with Boceprevir.Approved, Withdrawn
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Vildagliptin.Approved, Investigational
CabergolineThe serum concentration of Cabergoline can be increased when it is combined with Vildagliptin.Approved
CandoxatrilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Candoxatril.Experimental
CaptoprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Captopril.Approved
CarbamazepineThe metabolism of Vildagliptin can be increased when combined with Carbamazepine.Approved, Investigational
CarbutamideVildagliptin may increase the hypoglycemic activities of Carbutamide.Experimental
ChlorothiazideThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Chlorothiazide.Approved, Vet Approved
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Vildagliptin.Investigational, Withdrawn
ChlorpropamideVildagliptin may increase the hypoglycemic activities of Chlorpropamide.Approved
ChlorthalidoneThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Chlorthalidone.Approved
CilazaprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Cilazapril.Approved
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Vildagliptin.Approved
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with Vildagliptin.Approved, Vet Approved
Conjugated estrogensThe serum concentration of Conjugated estrogens can be decreased when it is combined with Vildagliptin.Approved
CyclobenzaprineThe serum concentration of Cyclobenzaprine can be increased when it is combined with Vildagliptin.Approved
CyclopenthiazideThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Cyclopenthiazide.Experimental
CyclophosphamideThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Vildagliptin.Approved, Investigational, Vet Approved
DelaprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Delapril.Experimental
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Vildagliptin.Approved
DesipramineThe serum concentration of Desipramine can be increased when it is combined with Vildagliptin.Approved
DibenzepinThe serum concentration of Dibenzepin can be increased when it is combined with Vildagliptin.Experimental
DienestrolThe serum concentration of Dienestrol can be decreased when it is combined with Vildagliptin.Approved, Investigational
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Vildagliptin.Approved, Investigational
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Vildagliptin.Approved
DiltiazemThe metabolism of Diltiazem can be decreased when combined with Vildagliptin.Approved
DosulepinThe serum concentration of Dosulepin can be increased when it is combined with Vildagliptin.Approved
DoxepinThe serum concentration of Doxepin can be increased when it is combined with Vildagliptin.Approved
EnalaprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Enalaprilat.Approved
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Vildagliptin.Approved, Investigational
EsmirtazapineThe serum concentration of Esmirtazapine can be increased when it is combined with Vildagliptin.Investigational
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Vildagliptin.Approved, Investigational, Vet Approved
EstramustineThe serum concentration of Estramustine can be decreased when it is combined with Vildagliptin.Approved
Estrogens, esterifiedThe serum concentration of Estrogens, esterified can be decreased when it is combined with Vildagliptin.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be decreased when it is combined with Vildagliptin.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Vildagliptin.Approved
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Vildagliptin.Approved
FosinoprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Fosinopril.Approved
GarlicThe serum concentration of Vildagliptin can be decreased when it is combined with Garlic.Approved
GlibornurideVildagliptin may increase the hypoglycemic activities of Glibornuride.Investigational, Withdrawn
GliclazideVildagliptin may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideVildagliptin may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideVildagliptin may increase the hypoglycemic activities of Glipizide.Approved
GliquidoneVildagliptin may increase the hypoglycemic activities of Gliquidone.Approved, Investigational
GlisoxepideVildagliptin may increase the hypoglycemic activities of Glisoxepide.Approved, Investigational
GlyburideVildagliptin may increase the hypoglycemic activities of Glyburide.Approved
HexestrolThe serum concentration of Hexestrol can be decreased when it is combined with Vildagliptin.Withdrawn
HydrochlorothiazideThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Hydroflumethiazide.Approved, Investigational
ImidaprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Imidapril.Investigational
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Vildagliptin.Approved
IndapamideThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Indapamide.Approved
Insulin HumanVildagliptin may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin PorkVildagliptin may increase the hypoglycemic activities of Insulin Pork.Approved
IprindoleThe serum concentration of Iprindole can be increased when it is combined with Vildagliptin.Experimental
Lipoic AcidLipoic Acid may increase the hypoglycemic activities of Vildagliptin.Approved, Nutraceutical
LisinoprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Lisinopril.Approved, Investigational
LofepramineThe serum concentration of Lofepramine can be increased when it is combined with Vildagliptin.Experimental
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Vildagliptin.Approved, Investigational
MedrogestoneThe serum concentration of Vildagliptin can be decreased when it is combined with Medrogestone.Approved
MestranolThe serum concentration of Mestranol can be decreased when it is combined with Vildagliptin.Approved
MetahexamideVildagliptin may increase the hypoglycemic activities of Metahexamide.Experimental
MethallenestrilThe serum concentration of Methallenestril can be decreased when it is combined with Vildagliptin.Experimental
MethyclothiazideThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Methyclothiazide.Approved
MethylergometrineThe serum concentration of Methylergometrine can be increased when it is combined with Vildagliptin.Approved
MetolazoneThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Metolazone.Approved
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Vildagliptin.Approved, Illicit
MirtazapineThe serum concentration of Mirtazapine can be increased when it is combined with Vildagliptin.Approved
MoexiprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Moexipril.Approved
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Vildagliptin.Approved, Withdrawn
NortriptylineThe serum concentration of Nortriptyline can be increased when it is combined with Vildagliptin.Approved
OmapatrilatThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Omapatrilat.Investigational
OpipramolThe serum concentration of Opipramol can be increased when it is combined with Vildagliptin.Investigational
PerindoprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Perindopril.Approved
PethidineThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Pethidine.Approved
PolythiazideThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Polythiazide.Approved
PregabalinThe risk or severity of heart failure can be increased when Pregabalin is combined with Vildagliptin.Approved, Illicit, Investigational
ProtriptylineThe serum concentration of Protriptyline can be increased when it is combined with Vildagliptin.Approved
QuinaprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Quinapril.Approved, Investigational
QuinethazoneThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Quinethazone.Approved
RamiprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Ramipril.Approved
RescinnamineThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Rescinnamine.Approved
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Vildagliptin.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Vildagliptin.Approved
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Vildagliptin.Approved, Investigational
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Vildagliptin.Approved
SpiraprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Spirapril.Approved
St. John's WortThe metabolism of Vildagliptin can be increased when combined with St. John's Wort.Investigational, Nutraceutical
Synthetic Conjugated Estrogens, AThe serum concentration of Synthetic Conjugated Estrogens, A can be decreased when it is combined with Vildagliptin.Approved
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Vildagliptin.Approved, Investigational
TemocaprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Temocapril.Experimental, Investigational
TemsirolimusThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Temsirolimus.Approved
TianeptineThe serum concentration of Tianeptine can be increased when it is combined with Vildagliptin.Approved, Investigational
TipranavirThe serum concentration of Vildagliptin can be decreased when it is combined with Tipranavir.Approved, Investigational
TolazamideVildagliptin may increase the hypoglycemic activities of Tolazamide.Approved
TolbutamideVildagliptin may increase the hypoglycemic activities of Tolbutamide.Approved
TrandolaprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Trandolapril.Approved
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Vildagliptin.Approved
TrichlormethiazideThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Trichlormethiazide.Approved, Vet Approved
TrimipramineThe serum concentration of Trimipramine can be increased when it is combined with Vildagliptin.Approved
UbidecarenoneThe therapeutic efficacy of Vildagliptin can be increased when used in combination with Ubidecarenone.Approved, Investigational, Nutraceutical
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Vildagliptin.Approved, Investigational
VerapamilThe metabolism of Verapamil can be decreased when combined with Vildagliptin.Approved
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Vildagliptin.Approved
ZofenoprilThe risk or severity of adverse effects can be increased when Vildagliptin is combined with Zofenopril.Experimental
Food Interactions
Not Available

References

Synthesis Reference

Stephen Winter, Jordi Bosch, Jordi Puig Serrano, Jose Javier Soto, "PROCESS FOR PREPARING VILDAGLIPTIN." U.S. Patent US20080167479, issued July 10, 2008.

US20080167479
General References
  1. 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]
External Links
Human Metabolome Database
HMDB15596
PubChem Compound
6918537
PubChem Substance
99443227
ChemSpider
5293734
BindingDB
11695
ChEBI
135285
ChEMBL
CHEMBL142703
PharmGKB
PA165958346
Wikipedia
Vildagliptin
ATC Codes
A10BH02 — VildagliptinA10BD08 — Metformin and vildagliptin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
1CompletedDiagnosticType 2 Diabetes Mellitus1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentType 2 Diabetes Mellitus4
1, 2CompletedTreatmentDiabetes Mellitus (DM) / Impaired Renal Function1
1, 2TerminatedBasic ScienceType 2 Diabetes Mellitus1
2CompletedBasic ScienceDiabetes Mellitus (DM)1
2CompletedTreatmentDiabetes Mellitus (DM)1
2CompletedTreatmentImpaired Glucose Tolerance (IGT) / Transplantation, Kidney1
2CompletedTreatmentType 2 Diabetes Mellitus2
2RecruitingTreatmentDiabetes, Diabetes Mellitus Type 11
2Unknown StatusTreatmentInsulin-dependent Gestational Diabetes1
2, 3CompletedTreatmentType 2 Diabetes Mellitus2
2, 3Unknown StatusBasic ScienceSDF-1 is an Important Cytokine for Neovascularization. Cleavage of SDF-1 is Reduced by DPPIV Inhibitors1
3CompletedPreventionEndothelial Dysfunction / Type 2 Diabetes Mellitus1
3CompletedPreventionInsulin Resistance / Microvascular Disease1
3CompletedTreatmentHealthy Volunteers / Type 2 Diabetes Mellitus1
3CompletedTreatmentImpaired Renal Function / Type 2 Diabetes Mellitus2
3CompletedTreatmentPre-Diabetic1
3CompletedTreatmentPrediabetic State1
3CompletedTreatmentType 2 Diabetes Mellitus61
3Not Yet RecruitingPreventionDiabetes Mellitus (DM) / Disorder Related to Renal Transplantation1
3RecruitingTreatmentDiabetes, Autoimmune / Diabetes, Diabetes Mellitus Type 1 / Insulin Dependent Diabetes / Juvenile Onset Diabetes Mellitus1
4Active Not RecruitingTreatmentType 2 Diabetes Mellitus2
4CompletedBasic ScienceDiabetes Mellitus (DM)1
4CompletedBasic ScienceDiabetes Mellitus (DM) / Hypoglycemia1
4CompletedBasic ScienceType 2 Diabetes Mellitus3
4CompletedTreatment1- Microvascular Function / 2-oxidative Stress / 3-inflammation1
4CompletedTreatmentChronic Foot Ulcers1
4CompletedTreatmentCongestive Heart Failure (CHF) / Type 2 Diabetes Mellitus1
4CompletedTreatmentDiabetes Mellitus (DM)1
4CompletedTreatmentDiabetes Mellitus, Non-Insulin-Dependent1
4CompletedTreatmentElderly / Type 2 Diabetes Mellitus1
4CompletedTreatmentEndothelial Dysfunction / High Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4CompletedTreatmentHaemodialyzed, Type 2 Diabetes1
4CompletedTreatmentHypoglycemia / Type 2 Diabetes Mellitus1
4CompletedTreatmentIschaemic Heart Diseases / Type 2 Diabetes Mellitus1
4CompletedTreatmentBone destruction / Menopause / Osteopenia / Type 2 Diabetes Mellitus1
4CompletedTreatmentReducing the Elevated Blood Pressure for Diabetic Hypertensive Patients1
4CompletedTreatmentType 2 Diabetes Mellitus18
4RecruitingTreatmentBMI >30 kg/m2 / Type 2 Diabetes Mellitus1
4RecruitingTreatmentIschaemic Heart Diseases / Type 2 Diabetes Mellitus1
4RecruitingTreatmentType 2 Diabetes Mellitus1
4TerminatedTreatmentType 2 Diabetes Mellitus1
4Unknown StatusTreatmentDiabetes Mellitus (DM) / Oxidative Stress1
4Unknown StatusTreatmentDiabetic Blood Glucose Monitoring / Exercise / Hypoglycemic Agents / Type 2 Diabetes Mellitus1
4Unknown StatusTreatmentType 2 Diabetes Mellitus2
Not AvailableCompletedNot AvailableType 2 Diabetes Mellitus3
Not AvailableNot Yet RecruitingNot AvailableType 2 Diabetes Mellitus1
Not AvailableRecruitingPreventionIncretinomimetics / Pancreas / Type 2 Diabetes Mellitus1
Not AvailableRecruitingTreatmentType 2 Diabetes Mellitus1
Not AvailableUnknown StatusNot AvailableType 2 Diabetes Mellitus1
Not AvailableUnknown StatusBasic ScienceTransplantation, Liver1
Not AvailableUnknown StatusBasic ScienceVagotomy, Truncal1
Not AvailableUnknown StatusTreatmentNon-Alcoholic Fatty Liver Disease (NAFLD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral50 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9313
Blood Brain Barrier+0.7886
Caco-2 permeable-0.6768
P-glycoprotein substrateSubstrate0.6301
P-glycoprotein inhibitor IInhibitor0.5624
P-glycoprotein inhibitor IIInhibitor0.9723
Renal organic cation transporterNon-inhibitor0.6373
CYP450 2C9 substrateNon-substrate0.7472
CYP450 2D6 substrateNon-substrate0.6984
CYP450 3A4 substrateSubstrate0.5965
CYP450 1A2 substrateNon-inhibitor0.8627
CYP450 2C9 inhibitorNon-inhibitor0.6428
CYP450 2D6 inhibitorNon-inhibitor0.7168
CYP450 2C19 inhibitorNon-inhibitor0.6922
CYP450 3A4 inhibitorNon-inhibitor0.866
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.7053
CarcinogenicityNon-carcinogens0.8895
BiodegradationNot ready biodegradable0.9959
Rat acute toxicity2.4274 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.853
hERG inhibition (predictor II)Inhibitor0.6939
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0109000000-f6f13525e0841cb9a0ce
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0902000000-39449b9fce86086b9f42
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-e42a57f8c41f08f0fe2b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-bdf96b3bb5758ccb2ee2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ue9-0900000000-813cd0c1f6616a3aac1a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0309000000-4cc7261ec4a8a5eb3c50
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0901000000-2828160e08a306467998
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-5900000000-797e5126c08d2be98d02
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f6t-9600000000-55a58d88d2018c5adff8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-9200000000-b511fd9b2243cdaf69cc
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0005-9100000000-5c5cb1119f70d6852572
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-1709000000-d62dc38a0bb019fd4bed

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
N-acylpyrrolidines / Tertiary carboxylic acid amides / Tertiary alcohols / Cyclic alcohols and derivatives / Nitriles / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Alpha-amino acid amide / N-acylpyrrolidine / Cyclic alcohol / Pyrrolidine / Tertiary alcohol / Tertiary carboxylic acid amide / Carboxamide group / Secondary aliphatic amine / Carbonitrile / Nitrile
show 14 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Dipeptidyl peptidase 4
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Virus receptor 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 bindi...
Gene Name
DPP4
Uniprot ID
P27487
Uniprot Name
Dipeptidyl peptidase 4
Molecular Weight
88277.935 Da
References
  1. 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]
  2. 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]
  3. 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]

Drug created on October 20, 2007 05:50 / Updated on November 09, 2017 03:48