Gosogliptin

Identification

Name
Gosogliptin
Accession Number
DB08382  (DB12502)
Type
Small Molecule
Groups
Investigational
Description

Gosogliptin has been used in trials studying the treatment of Renal Insufficiency, Chronic.

Structure
Thumb
Synonyms
  • 2-(4-{(3S,5S)-5-[(3,3-difluoropyrrolidin-1-yl)carbonyl]pyrrolidin-3-yl}piperazin-1-yl)pyrimidine
External IDs
PF-00734200 / PF-734,200 / PF-734200
Categories
UNII
GI718UO477
CAS number
869490-23-3
Weight
Average: 366.4089
Monoisotopic: 366.19796583
Chemical Formula
C17H24F2N6O
InChI Key
QWEWGXUTRTXFRF-KBPBESRZSA-N
InChI
InChI=1S/C17H24F2N6O/c18-17(19)2-5-25(12-17)15(26)14-10-13(11-22-14)23-6-8-24(9-7-23)16-20-3-1-4-21-16/h1,3-4,13-14,22H,2,5-12H2/t13-,14-/m0/s1
IUPAC Name
2-{4-[(3S,5S)-5-(3,3-difluoropyrrolidine-1-carbonyl)pyrrolidin-3-yl]piperazin-1-yl}pyrimidine
SMILES
[H][C@]1(CN[C@@]([H])(C1)C(=O)N1CCC(F)(F)C1)N1CCN(CC1)C1=NC=CC=N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ADipeptidyl peptidase 4Not AvailableHuman
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
AcetazolamideThe therapeutic efficacy of Gosogliptin can be increased when used in combination with Acetazolamide.
Acetylsalicylic acidAcetylsalicylic acid may increase the hypoglycemic activities of Gosogliptin.
AmcinonideThe therapeutic efficacy of Gosogliptin can be decreased when used in combination with Amcinonide.
Aminosalicylic AcidAminosalicylic Acid may increase the hypoglycemic activities of Gosogliptin.
AmitriptylineAmitriptyline may decrease the hypoglycemic activities of Gosogliptin.
AmoxapineAmoxapine may decrease the hypoglycemic activities of Gosogliptin.
ArticaineThe therapeutic efficacy of Gosogliptin can be decreased when used in combination with Articaine.
BenazeprilThe risk or severity of angioedema can be increased when Gosogliptin is combined with Benazepril.
BendroflumethiazideThe therapeutic efficacy of Gosogliptin can be decreased when used in combination with Bendroflumethiazide.
BetamethasoneThe therapeutic efficacy of Gosogliptin can be decreased when used in combination with Betamethasone.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
11516136
PubChem Substance
99444853
ChemSpider
9690926
BindingDB
50249479
ChEMBL
CHEMBL515387
HET
PF2
Wikipedia
Gosogliptin
PDB Entries
3f8s

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentRenal Insufficiency,Chronic1
3CompletedTreatmentType 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 Solubility1.33 mg/mLALOGPS
logP0.17ALOGPS
logP0.4ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)9.38ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity93.03 m3·mol-1ChemAxon
Polarizability36.61 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8873
Caco-2 permeable-0.6669
P-glycoprotein substrateSubstrate0.648
P-glycoprotein inhibitor IInhibitor0.6514
P-glycoprotein inhibitor IINon-inhibitor0.6933
Renal organic cation transporterInhibitor0.5225
CYP450 2C9 substrateNon-substrate0.8559
CYP450 2D6 substrateNon-substrate0.6078
CYP450 3A4 substrateSubstrate0.5847
CYP450 1A2 substrateInhibitor0.6332
CYP450 2C9 inhibitorInhibitor0.5428
CYP450 2D6 inhibitorNon-inhibitor0.7807
CYP450 2C19 inhibitorNon-inhibitor0.5508
CYP450 3A4 inhibitorNon-inhibitor0.6445
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5971
Ames testNon AMES toxic0.6791
CarcinogenicityNon-carcinogens0.9048
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.6944 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8928
hERG inhibition (predictor II)Inhibitor0.9126
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 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

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-arylpiperazines / Pyrrolidinecarboxamides / Dialkylarylamines / N-acylpyrrolidines / Aminopyrimidines and derivatives / N-alkylpiperazines / Tertiary carboxylic acid amides / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds
show 7 more
Substituents
Alpha-amino acid amide / N-arylpiperazine / N-acylpyrrolidine / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Dialkylarylamine / Aminopyrimidine / N-alkylpiperazine / 1,4-diazinane / Piperazine
show 25 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Dipeptidyl peptidase 4
Kind
Protein
Organism
Human
Pharmacological action
Yes
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. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
  2. Dai H, Johnson SL, Terra SG, Marbury TC, Smith WB, Alcorn H, Boyd RA, Wang R, Nguyen TT: The pharmacokinetics of PF-734200, a DPP-IV inhibitor, in subjects with renal insufficiency. Br J Clin Pharmacol. 2011 Jul;72(1):85-91. doi: 10.1111/j.1365-2125.2011.03954.x. [PubMed:21366665]

Drug created on September 15, 2010 15:31 / Updated on October 01, 2018 14:36