General Information of Drug (ID: DR1188)
Drug Name
Olaparib
Synonyms
Olaparib; Olaparib (AZD2281, Ku-0059436); WOH1JD9AR8; KU-0059436; KU-59436; Lynparza; 1-(Cyclopropylcarbonyl)-4-[5-[(3,4-dihydro-4-oxo-1-phthalazinyl)methyl]-2-fluorobenzoyl]piperazine; 4-(3-(4-(Cyclopropanecarbonyl)piperazine-1-carbonyl)-4-fluorobenzyl)phthalazin-1(2H)-one; 4-[3-(4-Cyclopropanecarbonyl-piperazine-1-carbonyl)-4-fluoro-benzyl]-2H-phthalazin-1-one; 763113-22-0; AZD 2281; AZD-2281; AZD2281; AZD2281(olaparib); CHEBI:83766; MFCD13185161; UNII-WOH1JD9AR8
Indication Ovarian cancer [ICD11: 2C73] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 434.5 Topological Polar Surface Area 82.1
Heavy Atom Count 32 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
23725625
PubChem SID
47209066 ; 56053773 ; 57299275 ; 85197660 ; 93581006 ; 99436961 ; 103605183 ; 109692964 ; 117670453 ; 118049496 ; 121277945 ; 123051082 ; 124490470 ; 124756970 ; 124947876 ; 125163775 ; 125312522 ; 125415525 ; 126582065 ; 126626885 ; 126644879 ; 126664211 ; 126666996 ; 126738835 ; 131407195 ; 131465127 ; 134213960 ; 134222742 ; 134338825 ; 134339140 ; 134346179 ; 134964396 ; 135261055 ; 135697767 ; 135708109 ; 135723596 ; 135727477 ; 136368068 ; 136377786 ; 136895641 ; 136920280 ; 137005640 ; 137255348 ; 141853509 ; 143499369 ; 144115666 ; 152237700 ; 152258100 ; 152344243 ; 160646939
ChEBI ID
CHEBI:83766
CAS Number
763113-22-0
TTD Drug ID
D0J9HW
Formula
C24H23FN4O3
Canonical SMILES
C1CC1C(=O)N2CCN(CC2)C(=O)C3=C(C=CC(=C3)CC4=NNC(=O)C5=CC=CC=C54)F
InChI
1S/C24H23FN4O3/c25-20-8-5-15(14-21-17-3-1-2-4-18(17)22(30)27-26-21)13-19(20)24(32)29-11-9-28(10-12-29)23(31)16-6-7-16/h1-5,8,13,16H,6-7,9-12,14H2,(H,27,30)
InChIKey
FDLYAMZZIXQODN-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
Olaparib metabolite M1 DM002291 N. A. Hydrolysis - Amide Hydrolysis 1 [3]
Olaparib metabolite M10 DM002288 N. A. Oxidation - Hydroxylation 1 [3]
Olaparib metabolite M2,M5,M6,M7 DM002283 N. A. Oxidation - Hydroxylation 1 [3]
Olaparib metabolite M11 DM002287
78673863
Other reaction - Dehydration 2 [3]
Olaparib metabolite M12 DM002290 N. A. Oxidation - Alcohol Oxidation 2 [3]
Olaparib metabolite M3 DM002286 N. A. Oxidation - Alcohol Oxidation 2 [3]
Olaparib metabolite M4 DM002289 N. A. Oxidation - Dehydrogenation 2 [3]
Olaparib metabolite M8 DM002284 N. A. Oxidation - Hydroxylation 2 [3]
Olaparib metabolite M9 DM002285 N. A. Oxidation - N-Dealkylation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001813 Olaparib Olaparib metabolite M2,M5,M6,M7 Oxidation - Hydroxylation Unclear [3]
MR001814 Olaparib Olaparib metabolite M10 Oxidation - Hydroxylation Unclear [3]
MR001815 Olaparib Olaparib metabolite M1 Hydrolysis - Amide Hydrolysis Unclear [3]
MR001811 Olaparib metabolite M10 Olaparib metabolite M4 Oxidation - Dehydrogenation Unclear [3]
MR001812 Olaparib metabolite M10 Olaparib metabolite M12 Oxidation - Alcohol Oxidation CYP3A4 ... [3]
MR001807 Olaparib metabolite M2,M5,M6,M7 Olaparib metabolite M8 Oxidation - Hydroxylation Unclear [3]
MR001808 Olaparib metabolite M2,M5,M6,M7 Olaparib metabolite M3 Oxidation - Alcohol Oxidation Unclear [3]
MR001809 Olaparib metabolite M2,M5,M6,M7 Olaparib metabolite M11 Other reaction - Dehydration Unclear [3]
MR001810 Olaparib metabolite M8 Olaparib metabolite M9 Oxidation - N-Dealkylation 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]
References
1 Olaparib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Extent of radiosensitization by the PARP inhibitor olaparib depends on its dose, the radiation dose and the integrity of the homologous recombination pathway of tumor cells. Radiother Oncol. 2015 Sep;116(3):358-65.
3 In vitro metabolism of olaparib in liver microsomes by liquid chromatography/electrospray ionization high-resolution mass spectrometry Rapid Commun Mass Spectrom. 2020 Feb 15;34(3):e8575. doi: 10.1002/rcm.8575.

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