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Details

Stereochemistry ACHIRAL
Molecular Formula C25H25ClN6O4S
Molecular Weight 541.022
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PILARALISIB

SMILES

COC1=CC=C(Cl)C(NC2=C(NS(=O)(=O)C3=CC=CC(NC(=O)C(C)(C)N)=C3)N=C4C=CC=CC4=N2)=C1

InChI

InChIKey=QINPEPAQOBZPOF-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C25H25ClN6O4S
Molecular Weight 541.022
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Pilaralisib (XL147, SAR245408) is a potent and highly selective inhibitor of class I phosphatidylinositol 3-kinase (PI3K) (α, β, γ, and δ). In cellular assays, XL147 inhibits the formation of PIP3 in the membrane, and inhibits phosphorylation of AKT, p70S6K, and S6 in multiple tumor cell lines with diverse genetic alterations affecting the PI3K pathway. In a panel of tumor cell lines, XL147 inhibits proliferation with a wide range of potencies, with evidence of an impact of genotype on sensitivity. Repeat-dose administration of XL147 results in significant tumor growth inhibition in multiple human xenograft models in nude mice. Pilaralisib, was being developed by Exelixis and its licensee, Sanofi (formerly sanofi-aventis), for the treatment of solid tumours. However, the product was not listed on Sanofi's early stage pipeline as of end of July 2015 and there have been no recent reports on development identified.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
The Selective PI3K Inhibitor XL147 (SAR245408) Inhibits Tumor Growth and Survival and Potentiates the Activity of Chemotherapeutic Agents in Preclinical Tumor Models.
2015 Apr
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Interim data from a phase I study showed that eight of 23 evaluable patients with non-small cell lung cancer, basal cell carcinoma, chondrosarcoma, or prostate cancer receiving pilaralisib treatment achieved a stable disease for >3 months and six of whom subsequently progressed. In this trial, patients were treated with one of seven dose levels of Pilaralisib (XL147, SAR245408), ranging from 30mg to 900mg daily, on 28-day cycles with a 21 days on and seven days off schedule
Route of Administration: Oral
In Vitro Use Guide
Pilaralisib (XL147, SAR245408) inhibits B16 melanoma cell migration (370-3333 nM), PC-3 cell migration (13-3333 nM), and VEGF-induced HMVEC tubule formation (370-1000 nM)
Substance Class Chemical
Created
by admin
on Tue Oct 22 01:38:11 UTC 2019
Edited
by admin
on Tue Oct 22 01:38:11 UTC 2019
Record UNII
60ES45KTMK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PILARALISIB
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
PILARALISIB [INN]
Common Name English
SAR245408
Code English
SAR-245408
Code English
XL147
Code English
PILARALISIB [WHO-DD]
Common Name English
2-AMINO-N-(3-(N-(3-((2-CHLORO-5-METHOXYPHENYL)AMINO)QUINOXALIN-2-YL)SULFAMOYL)PHENYL)-2-METHYLPROPANAMIDE
Systematic Name English
PILARALISIB [USAN]
Common Name English
2-AMINO-N-(3-((3-(2-CHLORO-5-METHOXYANILINO)QUINOXALIN-2-YL)SULFAMOYL(PHENYL)-2-METHYLPROPANAMIDE
Common Name English
XL-147
Code English
Classification Tree Code System Code
NCI_THESAURUS C129825
Created by admin on Tue Oct 22 01:38:11 UTC 2019 , Edited by admin on Tue Oct 22 01:38:11 UTC 2019
NCI_THESAURUS C2152
Created by admin on Tue Oct 22 01:38:11 UTC 2019 , Edited by admin on Tue Oct 22 01:38:11 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL3360203
Created by admin on Tue Oct 22 01:38:11 UTC 2019 , Edited by admin on Tue Oct 22 01:38:11 UTC 2019
PRIMARY
EVMPD
SUB32908
Created by admin on Tue Oct 22 01:38:11 UTC 2019 , Edited by admin on Tue Oct 22 01:38:11 UTC 2019
PRIMARY
CAS
934526-89-3
Created by admin on Tue Oct 22 01:38:11 UTC 2019 , Edited by admin on Tue Oct 22 01:38:11 UTC 2019
PRIMARY
NCI_THESAURUS
C71705
Created by admin on Tue Oct 22 01:38:11 UTC 2019 , Edited by admin on Tue Oct 22 01:38:11 UTC 2019
PRIMARY
PUBCHEM
56599306
Created by admin on Tue Oct 22 01:38:11 UTC 2019 , Edited by admin on Tue Oct 22 01:38:11 UTC 2019
PRIMARY
INN
9708
Created by admin on Tue Oct 22 01:38:11 UTC 2019 , Edited by admin on Tue Oct 22 01:38:11 UTC 2019
PRIMARY
CAS
1033110-57-4
Created by admin on Tue Oct 22 01:38:11 UTC 2019 , Edited by admin on Tue Oct 22 01:38:11 UTC 2019
SUPERSEDED
Related Record Type Details
ACTIVE MOIETY