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Dutogliptin

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Identification

Generic Name
Dutogliptin
DrugBank Accession Number
DB11723
Background

Dutogliptin has been investigated for the treatment of Diabetes Mellitus, Type II.

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 241.1
Monoisotopic: 241.159772
Chemical Formula
C10H20BN3O3
Synonyms
  • Dutogliptin
External IDs
  • PHX1149
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Dutogliptin is a potent and selective inhibitor of DPP4, a serine protease that has emerged as an important target for the treatment of type 2 diabetes. Inhibiting DPP4 increases the physiological levels of regulatory peptides, such as GLP-1, an important modulator of insulin response and digestion.

TargetActionsOrganism
ADipeptidyl peptidase 4
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

10-13 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Dutogliptin.
AcebutololThe therapeutic efficacy of Dutogliptin can be increased when used in combination with Acebutolol.
AcetazolamideThe therapeutic efficacy of Dutogliptin can be increased when used in combination with Acetazolamide.
AcetohexamideDutogliptin may increase the hypoglycemic activities of Acetohexamide.
Acetyl sulfisoxazoleThe therapeutic efficacy of Dutogliptin can be increased when used in combination with Acetyl sulfisoxazole.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dutogliptin Tartrate79QH89EV9M890402-81-0SVWHNLVZPGXBNS-MHDNXTQBSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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 / Boronic acids / Organic metalloid salts / Dialkylamines / Azacyclic compounds / Organic oxides / Monoalkylboranes / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic heteromonocyclic compound / Alkylborane / Alpha-amino acid amide / Amine / Azacycle / Boronic acid / Boronic acid derivative / Carbonyl group / Carboxamide group / Hydrocarbon derivative
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
38EAO245ZX
CAS number
852329-66-9
InChI Key
DVJAMEIQRSHVKC-BDAKNGLRSA-N
InChI
InChI=1S/C10H20BN3O3/c15-10(7-13-8-3-4-12-6-8)14-5-1-2-9(14)11(16)17/h8-9,12-13,16-17H,1-7H2/t8-,9+/m1/s1
IUPAC Name
[(2R)-1-(2-{[(3R)-pyrrolidin-3-yl]amino}acetyl)pyrrolidin-2-yl]boronic acid
SMILES
OB(O)[C@@H]1CCCN1C(=O)CN[C@@H]1CCNC1

References

General References
  1. O'Farrell AM, van Vliet A, Abou Farha K, Cherrington JM, Campbell DA, Li X, Hanway D, Li J, Guler HP: Pharmacokinetic and pharmacodynamic assessments of the dipeptidyl peptidase-4 inhibitor PHX1149: double-blind, placebo-controlled, single- and multiple-dose studies in healthy subjects. Clin Ther. 2007 Aug;29(8):1692-705. [Article]
PubChem Compound
11253490
PubChem Substance
347828085
ChemSpider
9428517
ZINC
ZINC000169746730

Clinical Trials

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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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3CompletedTreatmentType 2 Diabetes Mellitus1somestatusstop reasonjust information to hide
3Not Yet RecruitingTreatmentST Segment Elevation Myocardial Infarction (STEMI)1somestatusstop reasonjust information to hide
3TerminatedTreatmentImpaired Renal Function / Type 2 Diabetes Mellitus1somestatusstop reasonjust information to hide
3TerminatedTreatmentType 2 Diabetes Mellitus6somestatusstop reasonjust information to hide
2CompletedTreatmentAcute Myocardial Infarction (AMI) / Acute Myocardial Ischemia / ST Segment Elevation Myocardial Infarction (STEMI)1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.93 mg/mLALOGPS
logP-1.1ALOGPS
logP-2.4Chemaxon
logS-1.5ALOGPS
pKa (Strongest Acidic)8.63Chemaxon
pKa (Strongest Basic)10.1Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area84.83 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity58.91 m3·mol-1Chemaxon
Polarizability25.94 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002b-9300000000-f403b56c70744a57b83a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fr-0390000000-3ec71231be40da46de85
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fkc-0090000000-9f37260d6894fa2dbb9f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-4900000000-f519110e2077e5b9ff1c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9380000000-b509b2899a83b980acee
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-5930000000-989f600f81516222d88f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9720000000-2802555da8fcf3d479ae
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. Dipeptidyl peptidase 4
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation (PubMed:10900005, PubMed:10951221, PubMed:11772392, PubMed:17287217). Acts as a positive regulator of T-cell coactivation, by binding at least ADA, CAV1, IGF2R, and PTPRC (PubMed:10900005, PubMed:10951221, PubMed:11772392, PubMed:14691230). Its binding to CAV1 and CARD11 induces T-cell proliferation and NF-kappa-B activation in a T-cell receptor/CD3-dependent manner (PubMed:17287217). Its interaction with ADA also regulates lymphocyte-epithelial cell adhesion (PubMed:11772392). 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 (PubMed:10593948, PubMed:16651416). May be involved in the promotion of lymphatic endothelial cells adhesion, migration and tube formation (PubMed:18708048). When overexpressed, enhanced cell proliferation, a process inhibited by GPC3 (PubMed:17549790). 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 such as brain natriuretic peptide 32 (PubMed:10570924, PubMed:16254193). Removes N-terminal dipeptides sequentially from polypeptides having unsubstituted N-termini provided that the penultimate residue is proline (PubMed:10593948)
Specific Function
aminopeptidase activity
Gene Name
DPP4
Uniprot ID
P27487
Uniprot Name
Dipeptidyl peptidase 4
Molecular Weight
88277.935 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at October 20, 2016 20:42 / Updated at August 26, 2024 19:23