Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0074)
Drug Name
Alpelisib
Synonyms
Alpelisib (BYL719); NVP-BYL719; alpelisib; (2S)-N1-[4-Methyl-5-[2-(2,2,2-trifluoro-1,1-dimethylethyl)-4-pyridinyl]-2-thiazolyl]-1,2-pyrrolidinedicarboxamide; (S)-N1-(4-Methyl-5-(2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4-yl)thiazol-2-yl)pyrrolidine-1,2-dicarboxamide; 08W5N2C97Q; 1,2-Pyrrolidinedicarboxamide, N1-(4-methyl-5-(2-(2,2,2-trifluoro-1,1-dimethylethyl)-4-pyridinyl)-2-thiazolyl)-, (2S)-; 1217486-61-7; BYL 719; BYL-719; BYL719; C19H22F3N5O2S; CHEMBL2396661; UNII-08W5N2C97Q
Indication Breast cancer [ICD11: 2C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 441.5 Topological Polar Surface Area 129
Heavy Atom Count 30 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
56649450
PubChem SID
134426754 ; 140722288 ; 152159632 ; 152255399 ; 152258655 ; 160647491 ; 162012035 ; 163643246 ; 164041693 ; 172918746 ; 174486688 ; 174861534 ; 175448776 ; 176251621 ; 185965275 ; 198967672 ; 215785718 ; 223382725 ; 223626250 ; 225848216 ; 228076739 ; 244202215 ; 249565638 ; 252214078 ; 252451646 ; 252470926
ChEBI ID
CHEBI:93752
CAS Number
1217486-61-7
TTD Drug ID
D0W7HE
Formula
C19H22F3N5O2S
Canonical SMILES
CC1=C(SC(=N1)NC(=O)N2CCCC2C(=O)N)C3=CC(=NC=C3)C(C)(C)C(F)(F)F
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
InChIKey
STUWGJZDJHPWGZ-LBPRGKRZSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Alpelisib Metabolite M1 DM018026 N. A. Multi-steps Reaction - Glucuronidation; oxidation 1 [3]
Alpelisib Metabolite M12 DM018027 N. A. Conjugation - N-Glucuronidation 1 [3]
Alpelisib Metabolite M2 DM018028 N. A. Oxidation - Oxidation 1 [3]
Alpelisib Metabolite M3 DM018023 N. A. Oxidation - Oxidation 1 [3]
Alpelisib Metabolite M4 DM016847
156861546
Unclear - Unclear 1 [3]
Alpelisib Metabolite M9 DM018029 N. A. Oxidation - Oxidation 1 [3]
Alpelisib Metabolite M19 DM018025 N. A. Unclear - Unclear 2 [3]
Alpelisib Metabolite M8 DM018024 N. A. Oxidation - Oxidation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009835 Alpelisib Alpelisib Metabolite M3 Oxidation - Oxidation CYP3A4 [3]
MR009837 Alpelisib Alpelisib Metabolite M4 Unclear - Unclear Unclear [3]
MR009840 Alpelisib Alpelisib Metabolite M1 Multi-steps Reaction - Glucuronidation; oxidation Unclear [3]
MR009841 Alpelisib Alpelisib Metabolite M12 Conjugation - N-Glucuronidation UGT1A9 [3]
MR009842 Alpelisib Alpelisib Metabolite M2 Oxidation - Oxidation Unclear [3]
MR009843 Alpelisib Alpelisib Metabolite M9 Oxidation - Oxidation Unclear [3]
MR009836 Alpelisib Metabolite M3 Alpelisib Metabolite M8 Oxidation - Oxidation Unclear [3]
MR009838 Alpelisib Metabolite M4 Alpelisib Metabolite M8 Oxidation - Oxidation Unclear [3]
MR009839 Alpelisib Metabolite M4 Alpelisib Metabolite M19 Unclear - Unclear Unclear [3]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
References
1 Alpelisib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Comparison of 19F NMR and 14C measurements for the assessment of ADME of BYL719 (Alpelisib) in humans. Drug Metab Dispos. 2017 Aug;45(8):900-907.
3 Absorption, distribution, metabolism, and excretion of [(14)C]BYL719 (alpelisib) in healthy male volunteers. Cancer Chemother Pharmacol. 2015 Oct;76(4):751-60.

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