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Rucaparib phosphate

CAT: 0013-GTR19161952-09Size: 200 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19161952-09Size:200 mg
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Description
An inhibitor of PARP with Ki of 1.4 nM for PARP1 in a cell-free assay, also showing binding affinity to eight other PARP domains; inhibits PARP-1 activity by 97.1% at a concentration of 1 μM in permeabilised D283Med cells; enhances the antitumor activity of temozolomide and indicates complete and sustained tumor regression in NB1691 and SHSY5Y xenografts.Ovarian Cancer Approved (In Vitro) :Rucaparib (AG014699) phosphate is a possible N-demethylation metabolite of AG14644.Rucaparib (0.1, 1, 10, 100 μM; 24 hours) phosphate is cytotoxic and has the LC50 being 5 μM in Capan-1 (BRCA2 mutant) cells and only 100 nM in MX-1 (BRCA1 mutant) cells.The radio-sensitization by Rucaparib phosphate is due to downstream inhibition of activation of NF-κB, and is independent of SSB repair inhibition. Rucaparib phosphate can target NF-κB activated by DNA damage and overcome toxicity observed with classical NF-κB inhibitors without compromising other vital inflammatory functions.Rucaparib phosphate inhibits PARP-1 activity by 97.1% at a concentration of 1 μM in permeabilised D283Med cells. (In Vivo) :Rucaparib (AG014699) phosphate and AG14584 significantly increase Temozolomide toxicity. Rucaparib (1 mg/kg) phosphate significantly increases Temozolomide-induced body weight loss. Rucaparib (0.1 mg/kg) phosphate results in a 50% increase in the temozolomide-induced tumor growth delay.Rucaparib (10 mg/kg for i.p. or 50, 150 mg/kg for p.o.; daily for 5 days per week for 6 weeks) phosphate significantly inhibits the growth of the tumor, and there is one complete tumor regression and two persistent partial regressions.Rucaparib (150 mg/kg; p.o.; once per week for 6 weeks or three times per week for 6 weeks) phosphate has greatest antitumor effect with three complete regressions.Rucaparib phosphate enhances the antitumor activity of temozolomide and indicates complete and sustained tumor regression in NB1691 and SHSY5Y xenografts.
CAS Number
459868-92-9
Product Name Alternative
AG014699 phosphate | PF01367338 phosphate | AG 014699 phosphate
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
DMSO: ≥ 33 mg/mL
Smiles
OP (O) (O) =O.CNCC1=CC=C (C=C1) C1=C2CCNC (=O) C3=CC (F) =CC (N1) =C23 |c:9,11,14,24, t:7,21,28|
Molecular Formula
C19H21FN3O5P
Molecular Weight
421.3593
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
6H-Pyrrolo[4,3,2-ef][2]benzazepin-6-one, 8-fluoro-1,3,4,5-tetrahydro-2-[4-[ (methylamino) methyl]phenyl]-, phosphate (1:1)

Chemical Information

Rucaparib Phosphate

Rucaparib Phosphate is the phosphate salt form of rucaparib, an orally bioavailable tricyclic indole and inhibitor of poly(ADP-ribose) polymerases (PARPs) 1 (PARP1), 2 (PARP2) and 3 (PARP3), with potential chemo/radiosensitizing and antineoplastic activities. Upon administration, rucaparib selectively binds to PARP1, 2 and 3 and inhibits PARP-mediated DNA repair. This enhances the accumulation of DNA strand breaks, promotes genomic instability and induces cell cycle arrest and apoptosis. This may enhance the cytotoxicity of DNA-damaging agents and reverse tumor cell resistance to chemotherapy and radiation therapy. PARPs are enzymes activated by single-strand DNA breaks that catalyze the post-translational ADP-ribosylation of nuclear proteins, which induces signaling and the recruitment of other proteins to repair damaged DNA. The PARP-mediated repair pathway plays a key role in DNA repair and is dysregulated in a variety of cancer cell types.

CAS Number459868-92-9
PubChem CID9931953
IUPAC Name6-fluoro-2-[4-(methylaminomethyl)phenyl]-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one;phosphoric acid
Molecular FormulaC19H21FN3O5P
Molecular Weight421.4
Topological Polar Surface Area135
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Heavy Atom Count29
Formal Charge0
Complexity515
SMILES
CNCC1=CC=C(C=C1)C2=C3CCNC(=O)C4=C3C(=CC(=C4)F)N2.OP(=O)(O)O
InChI
InChI=1S/C19H18FN3O.H3O4P/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;1-5(2,3)4/h2-5,8-9,21,23H,6-7,10H2,1H3,(H,22,24);(H3,1,2,3,4)
InChIKey
FCCGJTKEKXUBFZ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Rucaparib Phosphate
CAS: 459868-92-9
CID: 9931953
Formula: C19H21FN3O5P
MW: 421.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight421.4
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Exact Mass421.12028594
Monoisotopic Mass421.12028594
Topological Polar Surface Area135 Ų
Heavy Atom Count29
Formal Charge0
Complexity515
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes