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Details

Stereochemistry ACHIRAL
Molecular Formula C19H18FN3O
Molecular Weight 323.3641
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RUCAPARIB

SMILES

CNCC1=CC=C(C=C1)C2=C3CCNC(=O)C4=CC(F)=CC(N2)=C34

InChI

InChIKey=HMABYWSNWIZPAG-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C19H18FN3O
Molecular Weight 323.3641
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Rucaparib is a poly (ADP-ribose) polymerase (PARP) inhibitor indicated for the treatment of advanced mutant BRCA ovarian cancer. Rucaparib is being investigated in clinical trials against prostate cancer, breast cancer and other neoplasms.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.804 nM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Potentiation of temozolomide and topotecan growth inhibition and cytotoxicity by novel poly(adenosine diphosphoribose) polymerase inhibitors in a panel of human tumor cell lines.
2000 Jul
Anticancer chemosensitization and radiosensitization by the novel poly(ADP-ribose) polymerase-1 inhibitor AG14361.
2004 Jan 7
Preclinical selection of a novel poly(ADP-ribose) polymerase inhibitor for clinical trial.
2007 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Recommended dose is 600 mg orally twice daily with or without food.
Route of Administration: Oral
In Vitro Use Guide
Exponentially proliferating cells were plated into six-well plates and incubated for 48 hours to allow cells to reach their optimum proliferation rate. AG014699 at 0, 0.1, 1.0, 10.0, 30.0, 50.0, or 100 μM in 1% dimethyl sulfoxide was added to the wells and incubated for 24 hours. Control cells received no AG014699 but were treated with medium containing 1% dimethyl sulfoxide for 24 hours. Cells were harvested and cultured in drug-free medium in 90-mm Petri dishes for up to 21 days, depending on the proliferation rate of the individual cell line. Colonies were fixed in methanol and acetic acid (3:1 vol/vol), stained with methyl violet 10B, and counted with an automated colony counter (Oxford Optronix, Oxford, UK). Data are expressed as the percentage of colonies in AG014699-treated cultures compared with that in control cultures. AG014699 (≤10 μM) was cytotoxic to cells with mutated BRCA1/2 or XRCC3 and to UACC3199 cells with epigenetically silenced BRCA1 but not to cells without BRCA1/2 or XRCC3 mutations or that were heterozygous for BRCA2 mutation
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:44:13 UTC 2019
Edited
by admin
on Mon Oct 21 20:44:13 UTC 2019
Record UNII
8237F3U7EH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RUCAPARIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
6H-AZEPINO(5,4,3-CD)INDOL-6-ONE, 8-FLUORO-1,3,4,5-TETRAHYDRO-2-(4-((METHYLAMINO)METHYL)PHENYL)-
Systematic Name English
RUCAPARIB [USAN]
Common Name English
RUCAPARIB [INN]
Common Name English
6H-PYRROLO(4,3,2-EF)(2)BENZAZEPIN-6-ONE, 8-FLUORO-1,3,4,5-TETRAHYDRO-2-(4-((METHYLAMINO)METHYL)PHENYL)-
Systematic Name English
RUCAPARIB [WHO-DD]
Common Name English
AG-14447
Code English
8-FLUORO-2-(4-((METHYLAMINO)METHYL)PHENYL)-1,3,4,5-TETRAHYDRO-6H-AZEPINO(5,4,3-CD)INDOL-6-ONE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C62554
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
WHO-ATC L01XX55
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
NDF-RT N0000191623
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
FDA ORPHAN DRUG 374712
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
EU-Orphan Drug EU/3/12/1049
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
Code System Code Type Description
EVMPD
SUB74859
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
PRIMARY
PUBCHEM
9931954
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
PRIMARY
ChEMBL
CHEMBL1173055
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
PRIMARY
RXCUI
1862579
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
PRIMARY
CAS
283173-50-2
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
PRIMARY
INN
9471
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
PRIMARY
NCI_THESAURUS
C137800
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
PRIMARY
EPA CompTox
283173-50-2
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
PRIMARY
WIKIPEDIA
RUCAPARIB
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
PRIMARY
NDF-RT
N0000191622
Created by admin on Mon Oct 21 20:44:13 UTC 2019 , Edited by admin on Mon Oct 21 20:44:13 UTC 2019
PRIMARY Poly(ADP-Ribose) Polymerase Inhibitors [MoA]
Related Record Type Details
TRANSPORTER -> SUBSTRATE
TARGET -> INHIBITOR
IC50
TRANSPORTER -> INHIBITOR
MODERATE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INHIBITOR
REVERSIBLE
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
In vitro, rucaparib was metabolized primarily by CYP2D6 and to a lesser extent by CYP1A2 and CYP3A4.
METABOLIC ENZYME -> INHIBITOR
REVERSIBLE
METABOLIC ENZYME -> INHIBITOR
TARGET -> INHIBITOR
IC50
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> INHIBITOR
REVERSIBLE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
In vitro, rucaparib was metabolized primarily by CYP2D6 and to a lesser extent by CYP1A2 and CYP3A4.
METABOLIC ENZYME -> INHIBITOR
REVERSIBLE
METABOLIC ENZYME -> INDUCER
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
blood-to-plasma ratio PHARMACOKINETIC