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

General Information of Drug (ID: DR1449)
Drug Name
Rucaparib
Synonyms
Rubraca; Rucaparib (free base); 283173-50-2; 6H-Pyrrolo[4,3,2-ef][2]benzazepin-6-one,8-fluoro-1,3,4,5-tetrahydro-2-[4-[(methylamino)methyl]phenyl]-; RUCAPARIB; 8-FLUORO-2-(4-((METHYLAMINO)METHYL)PHENYL)-4,5-DIHYDRO-1H-AZEPINO[5,4,3-CD]INDOL-6(3H)-ONE; 8-Fluoro-1,3,4,5-tetrahydro-2-[4-[(methylamino)methyl]phenyl]-6H-pyrrolo[4,3,2-ef][2]benzazepin-6-one; 8-fluoro-2-(4-methylaminomethyl-phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one; 8237F3U7EH; AG-14447; AK317822; UNII-8237F3U7EH
Indication Ovarian cancer [ICD11: 2C73] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 323.4 Topological Polar Surface Area 56.9
Heavy Atom Count 24 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
9931954
PubChem SID
16463842 ; 24207084 ; 76934109 ; 103769588 ; 103905261 ; 121278129 ; 128080164 ; 135626799 ; 137263927 ; 137276017 ; 142270192 ; 152037846 ; 162108736 ; 162829534 ; 164208495 ; 170474818 ; 172918029 ; 174006354 ; 177748908 ; 185992962 ; 194944026 ; 198980201 ; 210274713 ; 210280347 ; 223366069 ; 223471430 ; 223804825 ; 227116711 ; 249625884
ChEBI ID
CHEBI:94311
CAS Number
283173-50-2
TTD Drug ID
D01SHZ
Formula
C19H18FN3O
Canonical SMILES
CNCC1=CC=C(C=C1)C2=C3CCNC(=O)C4=C3C(=CC(=C4)F)N2
InChI
1S/C19H18FN3O/c1-21-10-11-2-4-12(5-3-11)18-14-6-7-22-19(24)15-8-13(20)9-16(23-18)17(14)15/h2-5,8-9,21,23H,6-7,10H2,1H3,(H,22,24)
InChIKey
HMABYWSNWIZPAG-UHFFFAOYSA-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
Rucaparib M309 metabolite DM001263
146620586
Oxidation - N-Demethylation 1 [3]
Rucaparib M323 metabolite DM001258 N. A. Oxidation - Oxidation 1 [3]
Rucaparib M324 metabolite DM001261
154409547
Oxidation - Oxidation 1 [3] , [4]
Rucaparib M337b metabolite DM001264 N. A. Oxidation - Oxidation 1 [3]
Rucaparib M337a metabolite DM001259 N. A. Conjugation - N-Methylation 2 [3]
Rucaparib M500 metabolite DM001262 N. A. Conjugation - Glucuronidation 2 [3] , [4]
Rucaparib metabolite M337C DM001260
156596515
Conjugation - N-Methylation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002210 Rucaparib Rucaparib M323 metabolite Oxidation - Oxidation CYP2D6 ... [3]
MR002211 Rucaparib Rucaparib M324 metabolite Oxidation - Oxidation CYP2D6 ... [3], [4]
MR002212 Rucaparib Rucaparib M309 metabolite Oxidation - N-Demethylation CYP2D6 ... [3]
MR002213 Rucaparib Rucaparib M337b metabolite Oxidation - Oxidation CYP2D6 ... [3]
MR002207 Rucaparib M323 metabolite Rucaparib M337a metabolite Conjugation - N-Methylation Unclear [3]
MR002208 Rucaparib M323 metabolite Rucaparib metabolite M337C Conjugation - N-Methylation Unclear [3]
MR002209 Rucaparib M324 metabolite Rucaparib M500 metabolite Conjugation - Glucuronidation UGT1A1 [3], [4]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
References
1 Rucaparib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Rucaparib: the past, present, and future of a newly approved PARP inhibitor for ovarian cancer. Onco Targets Ther. 2017 Jun 19;10:3029-3037.
3 Evaluation of absorption, distribution, metabolism, and excretion of [(14)C]-rucaparib, a poly(ADP-ribose) polymerase inhibitor, in patients with advanced solid tumors Invest New Drugs. 2020 Jun;38(3):765-775. doi: 10.1007/s10637-019-00815-2.
4 Pharmacokinetics and safety of rucaparib in patients with advanced solid tumors and hepatic impairment. Cancer Chemother Pharmacol. 2021 Aug;88(2):259-270. doi: 10.1007/s00280-021-04278-2.

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