Bisegliptin

Identification

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Name
Bisegliptin
Accession Number
DB06127
Type
Small Molecule
Groups
Investigational
Description

Bisegliptin is a compound for the treatment of type 2 diabetes. It is an orally active, dipeptidyl peptidase-IV (DPPIV) inhibitor which lowers blood glucose levels by blocking the degradation of the hormone GLP-1 thereby stimulating glucose-dependent insulin secretion and lowering blood glucose levels without hypoglycemic effects.

Structure
Thumb
Synonyms
Not Available
External IDs
KRP-104
Categories
UNII
9U5KQ79OK6
CAS number
862501-61-9
Weight
Average: 351.422
Monoisotopic: 351.195819872
Chemical Formula
C18H26FN3O3
InChI Key
AKFNKZFJBFQFAA-DIOPXHOYSA-N
InChI
InChI=1S/C18H26FN3O3/c1-2-25-16(24)17-3-6-18(7-4-17,8-5-17)21-11-15(23)22-12-13(19)9-14(22)10-20/h13-14,21H,2-9,11-12H2,1H3/t13-,14-,17?,18?/m0/s1
IUPAC Name
ethyl 4-({2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl}amino)bicyclo[2.2.2]octane-1-carboxylate
SMILES
[H][C@@]1(F)CN(C(=O)CNC23CCC(CC2)(CC3)C(=O)OCC)[C@@]([H])(C1)C#N

Pharmacology

Indication

Investigated for use/treatment in diabetes mellitus type 2.

Pharmacodynamics
Not Available
Mechanism of action

Bisegliptin is an orally active, dipeptidyl peptidase-IV (DPPIV) inhibitor which lowers blood glucose levels by blocking the degradation of the hormone GLP-1 thereby stimulating glucose-dependent insulin secretion and lowering blood glucose levels without hypoglycemic effects.

TargetActionsOrganism
UDipeptidyl peptidase 4Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Bisegliptin is combined with 2,4-thiazolidinedione.
5-(2-methylpiperazine-1-sulfonyl)isoquinolineThe therapeutic efficacy of Bisegliptin can be increased when used in combination with 5-(2-methylpiperazine-1-sulfonyl)isoquinoline.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypoglycemic activities of Bisegliptin.
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Bisegliptin.
AcetazolamideThe therapeutic efficacy of Bisegliptin can be increased when used in combination with Acetazolamide.
AcetohexamideBisegliptin may increase the hypoglycemic activities of Acetohexamide.
Acetyl sulfisoxazoleThe therapeutic efficacy of Bisegliptin can be increased when used in combination with Acetyl sulfisoxazole.
Acetylsalicylic acidAcetylsalicylic acid may increase the hypoglycemic activities of Bisegliptin.
AgmatineThe risk or severity of hypoglycemia can be increased when Agmatine is combined with Bisegliptin.
AICA ribonucleotideThe risk or severity of hypoglycemia can be increased when AICA ribonucleotide is combined with Bisegliptin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Link [Link]
External Links
PubChem Substance
347910337
ChemSpider
9863621

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentType 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.294 mg/mLALOGPS
logP0.82ALOGPS
logP0.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.43 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity88.4 m3·mol-1ChemAxon
Polarizability37.17 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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

Drug created on November 18, 2007 11:30 / Updated on June 04, 2019 06:21