U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22F3N5O2S
Molecular Weight 441.47
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALPELISIB

SMILES

CC1=C(SC(NC(=O)N2CCC[C@H]2C(N)=O)=N1)C3=CC(=NC=C3)C(C)(C)C(F)(F)F

InChI

InChIKey=STUWGJZDJHPWGZ-LBPRGKRZSA-N
InChI=1S/C19H22F3N5O2S/c1-10-14(11-6-7-24-13(9-11)18(2,3)19(20,21)22)30-16(25-10)26-17(29)27-8-4-5-12(27)15(23)28/h6-7,9,12H,4-5,8H2,1-3H3,(H2,23,28)(H,25,26,29)/t12-/m0/s1

HIDE SMILES / InChI

Description

Alpelisib (BYL719) is a PI3Kα-selective inhibitor. PI3K-AKT-mTOR pathway is frequently activated in cancer, therefore investigational PI3K inhibitor alpelisib is considered to be effective as an anticancer agent and has been in clinical development by Novartis. Alpelisib have demonstrated activity in preclinical models of solid tumors and had favorable tolerability profiles, with the most common adverse events consistent with “on-target” inhibition of PI3K in early clinical studies. There are ongoing clinical trials of alpelisib in a range of cancer types, including breast cancer, head and neck squamous cell carcinoma, non-small cell lung carcinoma, lymphoma, and glioblastoma multiforme. Combination therapy with other chemo therapeutics may be preferable.

Originator

Approval Year

TargetsConditions
PubMed

PubMed

TitleDatePubMed
Discovery of NVP-BYL719 a potent and selective phosphatidylinositol-3 kinase alpha inhibitor selected for clinical evaluation.
2013 Jul 1
Absorption, distribution, metabolism, and excretion of [(14)C]BYL719 (alpelisib) in healthy male volunteers.
2015 Oct
PI3K inhibitors as new cancer therapeutics: implications for clinical trial design.
2016
Activation of the PI3K/mTOR Pathway following PARP Inhibition in Small Cell Lung Cancer.
2016
[Current Progress and Feasibility of Using Molecular-Targeted Agent Combinations for Metastatic Colorectal Cancer].
2016 Apr
Treatment strategies for advanced hormone receptor-positive and human epidermal growth factor 2-negative breast cancer: the role of treatment order.
2016 Jan
PI3Kα inhibition reduces obesity in mice.
2016 Nov 4
A Phase Ib Study of Alpelisib (BYL719), a PI3Kα-Specific Inhibitor, with Letrozole in ER+/HER2- Metastatic Breast Cancer.
2017 Jan 1
Patents

Sample Use Guides

In Vivo Use Guide
Alpelisib (300 mg once daily) in combination with fulvestrant (500 mg; intramuscular injection on day 1 and day 15 of cycle 1, and then day 1 of each subsequent 28-day cycle) for men and postmenopausal women with hormone receptor positive, HER2-negative advanced breast cancer which progressed on or after aromatase inhibitor treatment.
Route of Administration: Oral
In Vitro Use Guide
Overexpression of FGFR1 in ER+/PIK3CA mutant breast cancer cells attenuated the response to alpelisib in vitro .
Name Type Language
ALPELISIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
(2S)-N1-(4-METHYL-5-(1-(1,1,1-TRIFLUORO-2-METHYLPROPAN-2-YL)PYRIDIN-4-YL)-1,3-THIAZOL-2-YL)PYRROLIDINE-1,2-DICARBOXAMIDE
Systematic Name English
NVP-BYL719
Code English
BYL719
Common Name English
ALPELISIB [INN]
Common Name English
1,2-PYRROLIDINEDICARBOXAMIDE, N1-(4-METHYL-5-(2-(2,2,2-TRIFLUORO-1,1-DIMETHYLETHYL)-4-PYRIDINYL)-2-THIAZOLYL)-, (2S)-
Systematic Name English
ALPELISIB [WHO-DD]
Common Name English
ALPELISIB [USAN]
Common Name English
BYL-719
Common Name English
(S)-PYRROLIDINE-1,2-DICARBOXYLIC ACID 2-AMIDE 1-(4-METHYL-5-(2-(2,2,2-TRIFLUORO-1,1-DIMETHYLETHYL)-PYRIDIN-4-YL)THIAZOL-2-YL)AMIDE
Common Name English
Code System Code Type Description
PUBCHEM
56649450
Created by admin on Tue Mar 06 10:59:35 UTC 2018 , Edited by admin on Tue Mar 06 10:59:35 UTC 2018
PRIMARY
EPA CompTox
1217486-61-7
Created by admin on Tue Mar 06 10:59:35 UTC 2018 , Edited by admin on Tue Mar 06 10:59:35 UTC 2018
PRIMARY
INN
9833
Created by admin on Tue Mar 06 10:59:35 UTC 2018 , Edited by admin on Tue Mar 06 10:59:35 UTC 2018
PRIMARY
EVMPD
SUB180707
Created by admin on Tue Mar 06 10:59:35 UTC 2018 , Edited by admin on Tue Mar 06 10:59:35 UTC 2018
PRIMARY
ChEMBL
CHEMBL2396661
Created by admin on Tue Mar 06 10:59:35 UTC 2018 , Edited by admin on Tue Mar 06 10:59:35 UTC 2018
PRIMARY
CAS
1217486-61-7
Created by admin on Tue Mar 06 10:59:35 UTC 2018 , Edited by admin on Tue Mar 06 10:59:35 UTC 2018
PRIMARY