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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 No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Sat Dec 16 06:49:18 UTC 2023
Edited
by admin
on Sat Dec 16 06:49:18 UTC 2023
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
VIJOICE
Brand Name English
NVP-BYL719
Code English
ALPELISIB [ORANGE BOOK]
Common Name English
ALPELISIB [MI]
Common Name English
BYL719
Code English
ALPELISIB [JAN]
Common Name English
Alpelisib [WHO-DD]
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
PIQRAY
Brand 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
Classification Tree Code System Code
FDA ORPHAN DRUG 930022
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
FDA ORPHAN DRUG 710819
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
NCI_THESAURUS C2152
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
NCI_THESAURUS C129825
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
Code System Code Type Description
USAN
EF-18
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
RXCUI
2169285
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
DRUG BANK
DB12015
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
SMS_ID
100000166553
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
WIKIPEDIA
Alpelisib
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
PUBCHEM
56649450
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
DRUG CENTRAL
5328
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID70153355
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
MERCK INDEX
m12147
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
NCI_THESAURUS
C94214
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
INN
9833
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
EVMPD
SUB180707
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
DAILYMED
08W5N2C97Q
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
ChEMBL
CHEMBL2396661
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
CAS
1217486-61-7
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
FDA UNII
08W5N2C97Q
Created by admin on Sat Dec 16 06:49:19 UTC 2023 , Edited by admin on Sat Dec 16 06:49:19 UTC 2023
PRIMARY
Related Record Type Details
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
The in vitro study result indicated that alpelisib is a weak P-gp inhibitor with a Ki of 98.6 μM (R0900459).
Ki
PHOSPHATIDYLINOSITOL 4,5-BISPHOSPHATE 3-KINASE CATALYTIC SUBUNIT ALPHA ISOFORM
TARGET -> INHIBITOR
IC50
PHOSPHATIDYLINOSITOL 4,5-BISPHOSPHATE 3-KINASE CATALYTIC SUBUNIT DELTA ISOFORM
TARGET -> INHIBITOR
IC50
PHOSPHATIDYLINOSITOL 4,5-BISPHOSPHATE 3-KINASE CATALYTIC SUBUNIT GAMMA ISOFORM
TARGET -> INHIBITOR
IC50
ADENOSINE RECEPTOR A3
OFF-TARGET->INHIBITOR
IC50
PHOSPHATIDYLINOSITOL 4,5-BISPHOSPHATE 3-KINASE CATALYTIC SUBUNIT BETA ISOFORM
TARGET -> INHIBITOR
IC50
ADENOSINE RECEPTOR A1
OFF-TARGET->INHIBITOR
IC50
Structure of ALPELISIB
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
In vitro, protein binding of alpelisib is 89% and is independent of concentration.
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Structure of ALPELISIB
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
In vitro, alpelisib is a strong time-dependent inhibitor of CYP3A4.
TIME-DEPENDENT INHIBITION
Ki
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INDUCER
STRONG
Related Record Type Details
Structure of ALPELISIB ACID
METABOLITE -> PARENT
MAJOR
FECAL; PLASMA; URINE
Related Record Type Details
Structure of ALPELISIB
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
blood-to-plasma ratio PHARMACOKINETIC
NIH
NCATS
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