Rucaparib Camsylate | CAS# 1859053-21-6 | PARP 1/2 Inhibitor

Rucaparib Camsylate
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WARNING: This product is for research use only, not for human or veterinary use.

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

Rucaparib Camsylate

CAS# 1859053-21-6 (camsylate)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 564307
Name: Rucaparib Camsylate
CAS#: 1859053-21-6 (camsylate)
Chemical Formula: C29H34FN3O5S
Exact Mass: 0.00
Molecular Weight: 555.670
Elemental Analysis:

Price and Availability

Size	Price	Availability
25mg	USD 90	Ready to ship
50mg	USD 150	Ready to ship
100mg	USD 250	Ready to ship
200mg	USD 450	Ready to ship
500mg	USD 950	Ready to ship
1g	USD 1650	Ready to ship
2g	USD 2950	Ready to ship
5g	USD 5850	Ready to ship
10g	USD 8950	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

More Info:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#A22T04K13

QC Data:

View QC data: current batch, Lot#A22T04K13

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

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	79.6	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.

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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1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548767/ PubMed PMID: 31644076.

2: Pearre DC, Tewari KS. Targeted treatment of advanced ovarian cancer: spotlight on rucaparib. Ther Clin Risk Manag. 2018 Nov 2;14:2189-2201. doi: 10.2147/TCRM.S149248. eCollection 2018. Review. PubMed PMID: 30464492; PubMed Central PMCID: PMC6223341.

3: Cosgrove CM, O'Malley DM. How safe is rucaparib in ovarian cancer? Expert Opin Drug Saf. 2018 Dec;17(12):1249-1255. doi: 10.1080/14740338.2018.1550067. Epub 2018 Dec 11. Review. PubMed PMID: 30449210.

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.

5: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK500908/ PubMed PMID: 29999967.

6: Dal Molin GZ, Omatsu K, Sood AK, Coleman RL. Rucaparib in ovarian cancer: an update on safety, efficacy and place in therapy. Ther Adv Med Oncol. 2018 Jun 22;10:1758835918778483. doi: 10.1177/1758835918778483. eCollection 2018. Review. PubMed PMID: 29977351; PubMed Central PMCID: PMC6024342.

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.

12: Syed YY. Rucaparib: First Global Approval. Drugs. 2017 Apr;77(5):585-592. doi: 10.1007/s40265-017-0716-2. Review. PubMed PMID: 28247266.

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.

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