NAV

Pilaralisib

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Pilaralisib
DrugBank Accession Number
DB11772
Background

Pilaralisib is an orally available small molecule that selectively inhibits the activity of phosphoinositide-3 kinase (PI3K). Pilaralisib has been used in trials studying the treatment of Cancer, Lymphoma, Solid Tumors, Glioblastoma, and Breast Cancer, among others.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 541.02
Monoisotopic: 540.1346522
Chemical Formula
C25H25ClN6O4S
Synonyms
  • Pilaralisib
External IDs
  • SAR-245408
  • SAR245408
  • XL-147
  • XL147
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

In preclinical studies, Pilaralisib slowed tumor growth or caused tumor shrinkage in multiple preclinical cancer models, including breast, lung, ovarian, and prostate cancers, and gliomas. Pilaralisib has also been shown to enhance the anti- tumor effects of several chemotherapeutic agents and an inhibitor of epidermal growth factor receptor (EGFR) in preclinical cancer models.

Mechanism of action

Pilaralisib is an orally available small molecule that selectively inhibits the activity of phosphoinositide-3 kinase (PI3K). Activation of PI3K is a frequent event in human tumors, promoting tumor cell growth, survival, and resistance to chemotherapy and radiotherapy. Inactivation of PI3K has been shown to inhibit growth and induce apoptosis (programmed cell death) in tumor cells.

TargetActionsOrganism
UPhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoformNot AvailableHumans
Absorption

Orally 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

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.
Not Available
Food Interactions
Not Available

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
Benzenesulfonamides / Quinoxalines / Benzenesulfonyl compounds / Anilides / Methoxyanilines / Phenoxy compounds / Anisoles / Methoxybenzenes / N-arylamides / Alkyl aryl ethers
show 14 more
Substituents
Alkyl aryl ether / Alpha-amino acid amide / Amine / Aminopyrazine / Aminosulfonyl compound / Anilide / Aniline or substituted anilines / Anisole / Aromatic heteropolycyclic compound / Aryl chloride
show 37 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
60ES45KTMK
CAS number
934526-89-3
InChI Key
QINPEPAQOBZPOF-UHFFFAOYSA-N
InChI
InChI=1S/C25H25ClN6O4S/c1-25(2,27)24(33)28-15-7-6-8-17(13-15)37(34,35)32-23-22(29-19-9-4-5-10-20(19)30-23)31-21-14-16(36-3)11-12-18(21)26/h4-14H,27H2,1-3H3,(H,28,33)(H,29,31)(H,30,32)
IUPAC Name
2-amino-N-[3-({3-[(2-chloro-5-methoxyphenyl)amino]quinoxalin-2-yl}sulfamoyl)phenyl]-2-methylpropanamide
SMILES
COC1=CC=C(Cl)C(NC2=C(NS(=O)(=O)C3=CC(NC(=O)C(C)(C)N)=CC=C3)N=C3C=CC=CC3=N2)=C1

References

General References
Not Available
PubChem Compound
56599306
PubChem Substance
347828124
ChemSpider
29340997
BindingDB
50197062
ChEMBL
CHEMBL3360203
ZINC
ZINC000100472223

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentEndometrial Cancer / Neoplasms, Endometrial1
1CompletedNot AvailableSolid Tumors1
1CompletedTreatmentAstrocytoma, Grade IV / High Grade Glioma: Glioblastoma (GBM)1
1CompletedTreatmentCancer (Solid Tumors)1
1CompletedTreatmentCancer / Endometrial Carcinoma / Non-Small Cell Lung Cancer (NSCLC) / Ovarian Carcinoma1

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 Solubility0.0048 mg/mLALOGPS
logP3.98ALOGPS
logP3.27Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)5.99Chemaxon
pKa (Strongest Basic)8.48Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area148.33 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity142.09 m3·mol-1Chemaxon
Polarizability52.89 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-0000090000-d0fcc4398ae9e3863623
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-0090000000-562536a44064815e91e1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1140290000-370d067a156fb27145d1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000420000-9aaa4abfb00ba77c98ef
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6x-4621940000-0c6aa3b5ca3e29643654
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9120510000-765cd464ec7f75fca0c0
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-215.71997
predicted
DeepCCS 1.0 (2019)
[M+H]+218.11555
predicted
DeepCCS 1.0 (2019)
[M+Na]+224.02808
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Phosphoinositide-3-kinase (PI3K) that phosphorylates PtdIns (Phosphatidylinositol), PtdIns4P (Phosphatidylinositol 4-phosphate) and PtdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate...
Gene Name
PIK3CA
Uniprot ID
P42336
Uniprot Name
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
Molecular Weight
124283.025 Da

Drug created at October 20, 2016 20:46 / Updated at February 21, 2021 18:53