Rucaparib free base
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MedKoo CAT#: 100947

CAS#: 283173-50-2 (free base)

Description: Rucaparib is a tricyclic indole poly(ADP-Ribose) polymerase (PARP1) inhibitor with potential chemosensitizing, radiosensitizing, and antineoplastic activities. Rucaparib selectively binds to PARP1 and inhibits PARP1-mediated DNA repair, thereby enhancing the accumulation of DNA strand breaks and promoting genomic instability and apoptosis.


Chemical Structure

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Rucaparib free base
CAS# 283173-50-2 (free base)

Theoretical Analysis

MedKoo Cat#: 100947
Name: Rucaparib free base
CAS#: 283173-50-2 (free base)
Chemical Formula: C19H18FN3O
Exact Mass: 323.1434
Molecular Weight: 323.3714
Elemental Analysis: C, 70.57; H, 5.61; F, 5.88; N, 12.99; O, 4.95

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 2 Weeks
2.0g USD 2950.0 2 Weeks
5.0g USD 5850.0 2 Weeks
10.0g USD 8950.0 2 Weeks
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Related CAS #: 283173-50-2 (free base)   459868-92-9 (phosphate)   1859053-21-6 (camsylate)  

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

IUPAC/Chemical Name: 8-Fluoro-2-(4-((methylamino)methyl)phenyl)-1,3,4,5-tetrahydro-6H-azepino(5,4,3-cd)indol-6-one

InChi Key: HMABYWSNWIZPAG-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C1NCCC2=C(C3=CC=C(CNC)C=C3)NC4=C2C1=CC(F)=C4

Appearance: Yellow 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 (up to 20mg/mL)

Shelf Life: >2 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 (AG014699) is an inhibitor of PARP with Ki of 1.4 nM for PARP1 in a cell-free assay.
In vitro activity: The absorption, distribution, metabolism, elimination, and drug-drug interaction (DDI) potential of the poly(ADP-ribose) polymerase (PARP) inhibitor rucaparib was characterised in vitro. Rucaparib showed moderate cellular permeability, moderate human plasma protein binding (70.2%), and slow metabolism in human liver microsomes (HLMs). In HLMs, cytochrome P450 (CYP) 1A2 and CYP3A contributed to the metabolism of rucaparib to its major metabolite M324 with estimated fractions of metabolism catalysed by CYP (fm,CYP) of 0.27 and 0.64, respectively. Rucaparib reversibly inhibited CYP1A2, CYP2C9, CYP2C19, CYP2D6, and CYP3As (IC50, 3.55, 12.9, 5.42, 41.6, and 17.2-22.9 µM [2 substrates], respectively), but not CYP2B6 or CYP2C8 (>190 µM). Reference: Xenobiotica. 2020 Sep;50(9):1032-1042. https://www.tandfonline.com/doi/abs/10.1080/00498254.2020.1737759?journalCode=ixen20
In vivo activity: The effects of rucaparib on the proliferation of cervical cancer cells and sensitivity to radiotherapy were investigated. Animal experiments were performed to evaluate tumor size after treatment with rucaparib. Immunohistochemistry was performed to analyze the expression of Ki-67. Rucaparib suppressed proliferation, induced G2/M phase arrest, and reduced the expression of cyclin D1 and CDK4 in cervical cancer cells. When rucaparib was combined with radiotherapy in cervical cancer cells, clone formation decreased significantly and G2/M phase arrest was accentuated. The expression of the DNA-damage marker ץ-H2AX was increased significantly, and rucaparib suppressed tumor growth in vivo. Rucaparib exerts significant anti-proliferative effects and can serve as an effective radiosensitizer in cervical cancer. Reference: Invest New Drugs. 2019 Feb;37(1):65-75. https://link.springer.com/article/10.1007%2Fs10637-018-0616-7

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 46.67 144.32
Ethanol 16.5 51.03
DMF 30.0 92.77
DMF:PBS(pH 7.2)(1:1) 0.5 1.55

Preparing Stock Solutions

The following data is based on the product molecular weight 323.3714 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. Liao M, Jaw-Tsai S, Beltman J, Simmons AD, Harding TC, Xiao JJ. Evaluation of in vitro absorption, distribution, metabolism, and excretion and assessment of drug-drug interaction of rucaparib, an orally potent poly(ADP-ribose) polymerase inhibitor. Xenobiotica. 2020 Sep;50(9):1032-1042. doi: 10.1080/00498254.2020.1737759. Epub 2020 Mar 18. PMID: 32129697. 2. Tang M, Liu Q, Zhou L, Chen L, Yang X, Yu J, Wang Y, Qiu H. The poly (ADP-ribose) polymerase inhibitor rucaparib suppresses proliferation and serves as an effective radiosensitizer in cervical cancer. Invest New Drugs. 2019 Feb;37(1):65-75. doi: 10.1007/s10637-018-0616-7. Epub 2018 Jun 6. PMID: 29872938.
In vitro protocol: 1. Liao M, Jaw-Tsai S, Beltman J, Simmons AD, Harding TC, Xiao JJ. Evaluation of in vitro absorption, distribution, metabolism, and excretion and assessment of drug-drug interaction of rucaparib, an orally potent poly(ADP-ribose) polymerase inhibitor. Xenobiotica. 2020 Sep;50(9):1032-1042. doi: 10.1080/00498254.2020.1737759. Epub 2020 Mar 18. PMID: 32129697.
In vivo protocol: 1. Tang M, Liu Q, Zhou L, Chen L, Yang X, Yu J, Wang Y, Qiu H. The poly (ADP-ribose) polymerase inhibitor rucaparib suppresses proliferation and serves as an effective radiosensitizer in cervical cancer. Invest New Drugs. 2019 Feb;37(1):65-75. doi: 10.1007/s10637-018-0616-7. Epub 2018 Jun 6. PMID: 29872938.

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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.

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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.