RPB

Rucaparib

Created:	2013-04-18
Last modified:	2014-09-05

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5 entries where RPB is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	42
Chiral Atom Count	0
Bond Count	45
Aromatic Bond Count	16

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Chemical Component Summary
Name	Rucaparib
Systematic Name (OpenEye OEToolkits)	n/a
Formula	C₁₉ H₁₈ F N₃ O
Molecular Weight	323.364
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	Fc4cc2c1c(nc(c1CCNC2=O)c3ccc(cc3)CNC)c4
SMILES	CACTVS	3.385	CNCc1ccc(cc1)c2[nH]c3cc(F)cc4C(=O)NCCc2c34
SMILES	OpenEye OEToolkits	1.9.2	CNCc1ccc(cc1)c2c3c4c(cc(cc4[nH]2)F)C(=O)NCC3
Canonical SMILES	CACTVS	3.385	CNCc1ccc(cc1)c2[nH]c3cc(F)cc4C(=O)NCCc2c34
Canonical SMILES	OpenEye OEToolkits	1.9.2	CNCc1ccc(cc1)c2c3c4c(cc(cc4[nH]2)F)C(=O)NCC3
InChI	InChI	1.03	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	InChI	1.03	HMABYWSNWIZPAG-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB12332
Name	Rucaparib
Groups	approved investigational
Description	Rucaparib is an anticancer drug and poly (ADP-ribose) polymerase (PARP) inhibitor. PARP is an enzyme that plays an essential role in DNA repair.[A18745] Rucaparib is proposed to work in several PARP-dependent and PARP-independent mechanisms of action; however, it causes a unique effect of synthetic lethality. By targeting the genetically-mutated cancer cells that lack a DNA repair mechanism, rucaparib causes cancer cell death and reduces tumour growth.[A18745,A31354] Rucaparib was granted FDA Breakthrough Therapy designation in April 2015 [A18745] and accelerated approval in December 2016.[A249240] The drug was later approved by the European Commission in May 2018.[L42185] It is currently used to treat recurrent ovarian and prostate cancer in adults.[L42155,L42185]
Synonyms	Rucaparib camsylate Rucaparib Rucaparib phosphate
Brand Names	Rubraca
Indication	Rucaparib is indicated for the maintenance treatment of adult patients with a deleterious BRCA mutation (germline and/or somatic)- associated recurrent epithelial ovarian, fallopian tube, or primary peritoneal cancer who are in a complete or partial response to platinum-based chemotherapy.[L44572] Under accelerated approval by the FDA, rucaparib is also indicated for the treatment of adult patients with a deleterious BRCA mutation (germline and/or somatic)-associated metastatic castration-resistant prostate cancer (mCRPC) who have been treated with androgen receptor-directed therapy and a taxane-based chemotherapy.[L44572]
Categories	Antineoplastic Agents Antineoplastic and Immunomodulating Agents BCRP/ABCG2 Inhibitors BCRP/ABCG2 Substrates Cytochrome P-450 CYP1A2 Inducers Cytochrome P-450 CYP1A2 Inducers (moderate) Cytochrome P-450 CYP1A2 Inhibitors Cytochrome P-450 CYP1A2 Inhibitors (weak) Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 Inhibitors (weak) Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (weak) Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (moderate) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (weak) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A5 Inhibitors Cytochrome P-450 CYP3A5 Inhibitors (strength unknown) Cytochrome P-450 CYP3A7 Inhibitors Cytochrome P-450 CYP3A7 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Enzyme Inhibitors Heterocyclic Compounds, Fused-Ring MATE 1 Inhibitors MATE 2 Inhibitors MATE inhibitors Narrow Therapeutic Index Drugs OAT1/SLC22A6 inhibitors OAT3/SLC22A8 Inhibitors OATP1B1/SLCO1B1 Inhibitors OATP1B3 inhibitors OCT1 inhibitors P-glycoprotein inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Poly (ADP-ribose) polymerase (PARP) inhibitors Poly(ADP-ribose) Polymerase Inhibitors UGT1A1 Inhibitors
ATC-Code	L01XK03
CAS number	283173-50-2

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Poly [ADP-ribose] polymerase 1	MAESSDKLYRVEYAKSGRASCKKCSESIPKDSLRMAIMVQSPMFDGKVPH...	unknown	inhibitor
Poly [ADP-ribose] polymerase 2	MAARRRRSTGGGRARALNESKRVNNGNTAPEDSSPAKKTRRCQRQESKKM...	unknown	inhibitor
Poly [ADP-ribose] polymerase 3	MAPKPKPWVQTEGPEKKKGRQAGREEDPFRSTAEALKAIPAEKRIIRVDP...	unknown	inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate,inhibitor
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate,inhibitor,inducer
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	inhibitor
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	inhibitor
Cytochrome P450 3A43	MDLIPNFAMETWVLVATSLVLLYIYGTHSHKLFKKLGIPGPTPLPFLGTI...	unknown	inhibitor
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	inhibitor
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	inhibitor
UDP-glucuronosyltransferase 1-1	MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...	unknown	inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate,inhibitor
Multidrug and toxin extrusion protein 1	MEAPEEPAPVRGGPEATLEVRGSRCLRLSAFREELRALLVLAGPAFLVQL...	unknown	inhibitor
Multidrug and toxin extrusion protein 2	MDSLQDTVALDHGGCCPALSRLVPRGFGTEMWTLFALSGPLFLFQVLTFM...	unknown	inhibitor
Solute carrier family 22 member 1	MPTVDDILEQVGESGWFQKQAFLILCLLSAAFAPICVGIVFLGFTPDHHC...	unknown	inhibitor
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	inhibitor
Solute carrier organic anion transporter family member 1B3	MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...	unknown	inhibitor
Solute carrier family 22 member 6	MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...	unknown	inhibitor
Solute carrier family 22 member 8	MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...	unknown	inhibitor
Multidrug resistance-associated protein 4	MLPVYQEVKPNPLQDANLCSRVFFWWLNPLFKIGHKRRLEEDDMYSVLPE...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682