Rucaparib Camsylate
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MedKoo CAT#: 564307

CAS#: 1859053-21-6 (camsylate)

Description: Rucaparib camsylate is a potent, orally available inhibitor of poly ADP-ribose polymerase (PARP) 1 and 2.


Chemical Structure

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Rucaparib Camsylate
CAS# 1859053-21-6 (camsylate)

Theoretical Analysis

MedKoo Cat#: 564307
Name: Rucaparib Camsylate
CAS#: 1859053-21-6 (camsylate)
Chemical Formula: C29H34FN3O5S
Exact Mass:
Molecular Weight: 555.67
Elemental Analysis:

Price and Availability

Size Price Availability Quantity
25.0mg USD 90.0 Ready to ship
50.0mg USD 150.0 Ready to ship
100.0mg USD 250.0 Ready to ship
200.0mg USD 450.0 Ready to ship
500.0mg USD 950.0 Ready to ship
1.0g USD 1650.0 Ready to ship
2.0g USD 2950.0 Ready to ship
5.0g USD 5850.0 Ready to ship
10.0g USD 8950.0 Ready to ship
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Related CAS #: 283173-50-2 (free base)   459868-92-9 (phosphate)   1859053-21-6 (camsylate)  

Synonym: AG14699 (as phosphate salt); AG 14699; AG-14699; AG014447 (as free base); AG-014447; AG 014447; PF01367338; PF-01367338; PF 01367338; Rucaparib camsylate; Rubraca;

IUPAC/Chemical Name: Bicyclo(2.2.1)heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S,4R)-, compd. with 8-fluoro-1,3,4,5-tetrahydro-2-(4-((methylamino)methyl)phenyl)-6H-pyrrolo(4,3,2-ef)(2)benzazepin-6-one (1:1)

InChi Key: InChI=1S/C19H18FN3O.C10H16O4S/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;1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h2-5,8-9,21,23H,6-7,10H2,1H3,(H,22,24);7H,3-6H2,1-2H3,(H,12,13,14)/t;7-,10-/m.1/s1

InChi Code: INBJJAFXHQQSRW-STOWLHSFSA-N

SMILES Code: O=S(C[C@@]1(C2(C)C)C(C[C@@]2([H])CC1)=O)(O)=O.O=C(NCC3)C4=CC(F)=CC5=C4C3=C(C6=CC=C(CNC)C=C6)N5

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Rucaparib (Rubraca, AG014699, PF01367338) Camsylate is 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.
In vitro activity: The ability of p65 to bind with its consensus sequence following either IR or TNF-α in p65+/+ or p65−/− MEFs was investigated. SiRNA targeting p65 or a combination of p65 siRNA and AG-014699 reduced DNA binding > 85% following IR in p65+/+ cells (p=0.008 and p=0.009, compared to IR alone, respectively). PARP-1 siRNA inhibited DNA binding by approximately 60% (p= 0.03, compared to IR). Significantly, AG-014699 also reduced IR-induced DNA binding to levels comparable with untreated controls (p=0.05, compared to IR). p65 siRNA or a combination of p65 siRNA and AG-014699 reduced DNA binding to levels relative to Mock treated controls, following TNF-α (p= 0.009 and p=0.007, compared to TNF-α alone, respectively). Importantly, PARP-1 siRNA also reduced DNA binding 25% after TNF-α treatment (p=0.02, compared to TNF-α). Reference: Oncogene. 2012 Jan 12;31(2):251-64. https://pubmed.ncbi.nlm.nih.gov/21706052/
In vivo activity: Vessel mismatch was markedly reduced in the AG14361 (10 mg/kg) pre-treated SW620 xenografts compared to control (18 versus 51%). Vessel mismatch was also reduced following AG014699 (1 mg/kg; 28%) and nicotinamide (1 g/kg; 19%) pre-treatment. Thus, AG014699 has a similar effect to a 10x higher concentration of AG14361 and a 1,000x higher concentration of nicotinamide. For AG014699 the amount of vessel closure was further reduced compared with AG14361 and nicotinamide to only 5% in mice treated with AG014699. Furthermore the proportion of vessels open at the time of carbocyanine injection was greater in AG014699 treated mice (21%) compared with AG14361 and nicotinamide (7% for both) and was comparable to controls. Furthermore the proportion of vessels open at the time of carbocyanine injection was greater in AG014699 treated mice (21%) compared with AG14361 and nicotinamide (7% for both), indicating that a substantial amount of the vessel mismatch was a consequence of vessel opening. Reference: Clin Cancer Res. 2009 Oct 1;15(19):6106-12. https://pubmed.ncbi.nlm.nih.gov/19789326/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 79.63 143.31

Preparing Stock Solutions

The following data is based on the product molecular weight 555.67 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Hunter JE, Willmore E, Irving JA, Hostomsky Z, Veuger SJ, Durkacz BW. NF-κB mediates radio-sensitization by the PARP-1 inhibitor, AG-014699. Oncogene. 2012 Jan 12;31(2):251-64. doi: 10.1038/onc.2011.229. Epub 2011 Jun 27. PMID: 21706052; PMCID: PMC3191117. 2. Murray J, Thomas H, Berry P, Kyle S, Patterson M, Jones C, Los G, Hostomsky Z, Plummer ER, Boddy AV, Curtin NJ. Tumour cell retention of rucaparib, sustained PARP inhibition and efficacy of weekly as well as daily schedules. Br J Cancer. 2014 Apr 15;110(8):1977-84. doi: 10.1038/bjc.2014.91. Epub 2014 Feb 20. PMID: 24556618; PMCID: PMC3992512. 3. Daniel RA, Rozanska AL, Thomas HD, Mulligan EA, Drew Y, Castelbuono DJ, Hostomsky Z, Plummer ER, Boddy AV, Tweddle DA, Curtin NJ, Clifford SC. Inhibition of poly(ADP-ribose) polymerase-1 enhances temozolomide and topotecan activity against childhood neuroblastoma. Clin Cancer Res. 2009 Feb 15;15(4):1241-9. doi: 10.1158/1078-0432.CCR-08-1095. Epub 2009 Jan 27. PMID: 19174487. 4. Ali M, Telfer BA, McCrudden C, O'Rourke M, Thomas HD, Kamjoo M, Kyle S, Robson T, Shaw C, Hirst DG, Curtin NJ, Williams KJ. Vasoactivity of AG014699, a clinically active small molecule inhibitor of poly(ADP-ribose) polymerase: a contributory factor to chemopotentiation in vivo? Clin Cancer Res. 2009 Oct 1;15(19):6106-12. doi: 10.1158/1078-0432.CCR-09-0398. Epub 2009 Sep 29. PMID: 19789326; PMCID: PMC2756456.
In vitro protocol: 1. Hunter JE, Willmore E, Irving JA, Hostomsky Z, Veuger SJ, Durkacz BW. NF-κB mediates radio-sensitization by the PARP-1 inhibitor, AG-014699. Oncogene. 2012 Jan 12;31(2):251-64. doi: 10.1038/onc.2011.229. Epub 2011 Jun 27. PMID: 21706052; PMCID: PMC3191117. 2. Murray J, Thomas H, Berry P, Kyle S, Patterson M, Jones C, Los G, Hostomsky Z, Plummer ER, Boddy AV, Curtin NJ. Tumour cell retention of rucaparib, sustained PARP inhibition and efficacy of weekly as well as daily schedules. Br J Cancer. 2014 Apr 15;110(8):1977-84. doi: 10.1038/bjc.2014.91. Epub 2014 Feb 20. PMID: 24556618; PMCID: PMC3992512.
In vivo protocol: 1. Daniel RA, Rozanska AL, Thomas HD, Mulligan EA, Drew Y, Castelbuono DJ, Hostomsky Z, Plummer ER, Boddy AV, Tweddle DA, Curtin NJ, Clifford SC. Inhibition of poly(ADP-ribose) polymerase-1 enhances temozolomide and topotecan activity against childhood neuroblastoma. Clin Cancer Res. 2009 Feb 15;15(4):1241-9. doi: 10.1158/1078-0432.CCR-08-1095. Epub 2009 Jan 27. PMID: 19174487. 2. Ali M, Telfer BA, McCrudden C, O'Rourke M, Thomas HD, Kamjoo M, Kyle S, Robson T, Shaw C, Hirst DG, Curtin NJ, Williams KJ. Vasoactivity of AG014699, a clinically active small molecule inhibitor of poly(ADP-ribose) polymerase: a contributory factor to chemopotentiation in vivo? Clin Cancer Res. 2009 Oct 1;15(19):6106-12. doi: 10.1158/1078-0432.CCR-09-0398. Epub 2009 Sep 29. PMID: 19789326; PMCID: PMC2756456.

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4: Dal Molin GZ, Westin SN, Coleman RL. Rucaparib in ovarian cancer: extending the use of PARP inhibitors in the recurrent disease. Future Oncol. 2018 Dec;14(30):3101-3110. doi: 10.2217/fon-2018-0215. Epub 2018 Aug 14. Review. PubMed PMID: 30105925; PubMed Central PMCID: PMC6331693.

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7: Colombo I, Lheureux S, Oza AM. Rucaparib: a novel PARP inhibitor for BRCA advanced ovarian cancer. Drug Des Devel Ther. 2018 Mar 21;12:605-617. doi: 10.2147/DDDT.S130809. eCollection 2018. Review. PubMed PMID: 29606854; PubMed Central PMCID: PMC5868608.

8: Musella A, Bardhi E, Marchetti C, Vertechy L, Santangelo G, Sassu C, Tomao F, Rech F, D'Amelio R, Monti M, Palaia I, Muzii L, Benedetti Panici P. Rucaparib: An emerging parp inhibitor for treatment of recurrent ovarian cancer. Cancer Treat Rev. 2018 May;66:7-14. doi: 10.1016/j.ctrv.2018.03.004. Epub 2018 Mar 23. Review. PubMed PMID: 29605737.

9: Mariappan L, Jiang XY, Jackson J, Drew Y. Emerging treatment options for ovarian cancer: focus on rucaparib. Int J Womens Health. 2017 Dec 15;9:913-924. doi: 10.2147/IJWH.S151194. eCollection 2017. Review. PubMed PMID: 29290694; PubMed Central PMCID: PMC5735986.

10: Moore DC, Ringley JT, Patel J. Rucaparib: A Poly(ADP-Ribose) Polymerase Inhibitor for BRCA-Mutated Relapsed Ovarian Cancer. J Pharm Pract. 2019 Apr;32(2):219-224. doi: 10.1177/0897190017743131. Epub 2017 Nov 22. Review. PubMed PMID: 29166829.

11: Dockery LE, Gunderson CC, Moore KN. Rucaparib: the past, present, and future of a newly approved PARP inhibitor for ovarian cancer. Onco Targets Ther. 2017 Jun 19;10:3029-3037. doi: 10.2147/OTT.S114714. eCollection 2017. Review. PubMed PMID: 28790837; PubMed Central PMCID: PMC5488752.

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13: Jenner ZB, Sood AK, Coleman RL. Evaluation of rucaparib and companion diagnostics in the PARP inhibitor landscape for recurrent ovarian cancer therapy. Future Oncol. 2016 Jun;12(12):1439-56. doi: 10.2217/fon-2016-0002. Epub 2016 Apr 18. Review. PubMed PMID: 27087632; PubMed Central PMCID: PMC4976841.