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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

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

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
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 .
Substance Class Chemical
Created
by admin
on Tue Mar 06 10:59:35 UTC 2018
Edited
by admin
on Tue Mar 06 10:59:35 UTC 2018
Record UNII
08W5N2C97Q
Record Status Validated (UNII)
Record Version
  • Download
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
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METABOLITE -> PARENT
MAJOR
FECAL; PLASMA; URINE
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