Rubitecan | Camptogen | Orathecin | CAS# 91421-42-0 | topoisomerase I

MedKoo Cat#: 202540 | Name: Rubitecan

Featured

Description:

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

Rubitecan is a semisynthetic agent related to camptothecin with potent antitumor and antiviral properties. Rubitecan binds to and inhibits the enzyme topoisomerase I and induces protein-linked DNA single-strand breaks, thereby blocking DNA and RNA synthesis in dividing cells; this agent also prevents repair of reversible single-strand DNA breaks.

Chemical Structure

Rubitecan

CAS#91421-42-0

Theoretical Analysis

MedKoo Cat#: 202540

Name: Rubitecan

CAS#: 91421-42-0

Chemical Formula: C20H15N3O6

Exact Mass: 393.0961

Molecular Weight: 393.35

Elemental Analysis: C, 61.07; H, 3.84; N, 10.68; O, 24.40

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 250.00
50mg	USD 500.00
100mg	USD 850.00

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

RFS 2000; RFS-2000; RFS2000; Abbreviation: 9NC. 9-nitro-camptothecin; 9-nitro-CPT; nitrocamptothecin. US brand names: Camptogen; Orathecin.

IUPAC/Chemical Name

(S)-4-ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

InChi Key

VHXNKPBCCMUMSW-FQEVSTJZSA-N

InChi Code

InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1

SMILES Code

O=C1[C@](O)(CC)C2=C(CO1)C(N3CC4=CC5=C([N+]([O-])=O)C=CC=C5N=C4C3=C2)=O

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, not soluble in water.

Shelf Life

>5 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

According to BioSpace, EuroGen Pharmaceuticals Ltd. has withdrawn its Marketing Authorisation Application for OrathecinÂ™ (rubitecan), following discussions with the EMEA. Orathecin is a topoisomerase I inhibitor under development for the treatment of pancreatic cancer in patients who have failed at least one prior chemotherapy regimen. According to a press release from the EMEA, the Committee for Medicinal Products for Human Use (CHMP) reviewed Phase III data submitted as part of the application and did not consider it to be sufficient to demonstrate a clinical benefit for patients receiving Orathecin. The Company could not address the issues raised at this stage and therefore withdrew the application. Orathecin has orphan drug status in both the US and the EU. An ongoing US Phase II trial is looking at a combination of Orathecin and gemcitabine as a first-line combination therapy for advanced pancreatic cancer patients who are chemotherapy naive. See: http://www.nelm.nhs.uk/en/NeLM-Area/News/486153/486361/486372/ .

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 393.35 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

1: Zhou H, Zhang Y, Tian Y, Sun Y, Chen Y, Zhang Y, Zhu Q, Pan J, Qing C. 9-Nitro-20(S)-carbonate-camptothecin (NCP4), a novel prodrug of 9-nitrocamptothecin (9-NC), exhibits potent chemotherapeutic efficacy and improved safety against hepatocarcinoma. Eur J Pharmacol. 2022 May 15;923:174898. doi: 10.1016/j.ejphar.2022.174898. Epub 2022 Mar 17. PMID: 35305999. 2: Partridge FA, Poulton BC, Lake MAI, Lees RA, Mann HJ, Lycett GJ, Sattelle DB. Actions of Camptothecin Derivatives on Larvae and Adults of the Arboviral Vector Aedes aegypti. Molecules. 2021 Oct 15;26(20):6226. doi: 10.3390/molecules26206226. PMID: 34684807; PMCID: PMC8540655. 3: Tsikarishvili S, Karapetian M, Kulikova N, Zaalishvili G. PARP inhibition suppresses topoisomerase 1 poisoning induced Caspase-3 dependent cell death in zebrafish embryos. Biochem Biophys Res Commun. 2021 Apr 23;550:166-170. doi: 10.1016/j.bbrc.2021.03.005. Epub 2021 Mar 8. PMID: 33706100. 4: Elmezayen AD, Al-Obaidi A, Şahin AT, Yelekçi K. Drug repurposing for coronavirus (COVID-19): in silico screening of known drugs against coronavirus 3CL hydrolase and protease enzymes. J Biomol Struct Dyn. 2021 May;39(8):2980-2992. doi: 10.1080/07391102.2020.1758791. Epub 2020 Apr 26. PMID: 32306862; PMCID: PMC7189413. 5: Wang Z, Shao C, Hu Z, Zheng J, Zhang Q, Kou X, Wang Z, Yu T, Cao Z, Wang Y. The development and validation of an LC-MS/MS method for the quantification of CZ112, a prodrug of 9-Nitrocamptothecin in rat plasma. J Pharm Biomed Anal. 2020 Feb 5;179:112963. doi: 10.1016/j.jpba.2019.112963. Epub 2019 Nov 10. PMID: 31848079. 6: Ru G, Han L, Qing J, Sheng J, Li R, Qiu M, Wang J. Effects of borneol on the pharmacokinetics of 9-nitrocamptothecin encapsulated in PLGA nanoparticles with different size via oral administration. Drug Deliv. 2016 Nov;23(9):3417-3423. doi: 10.1080/10717544.2016.1189466. Epub 2016 Jun 1. PMID: 27174642. 7: Huang Y, Wang H, Liu G, Jiang Y. New polymorphs of 9-nitro-camptothecin prepared using a supercritical anti-solvent process. Int J Pharm. 2015 Dec 30;496(2):551-60. doi: 10.1016/j.ijpharm.2015.10.079. Epub 2015 Nov 2. PMID: 26541305. 8: Chen J, Lu S, Gu W, Peng P, Dong J, Xu F, Yang X, Xiong Z, Yang X. Characterization of 9-nitrocamptothecin-in-cyclodextrin-in-liposomes modified with transferrin for the treating of tumor. Int J Pharm. 2015 Jul 25;490(1-2):219-28. doi: 10.1016/j.ijpharm.2015.05.047. Epub 2015 May 21. PMID: 26004006. 9: Lian X, Dong J, Zhang J, Teng Y, Lin Q, Fu Y, Gong T. Soluplus(®) based 9-nitrocamptothecin solid dispersion for peroral administration: preparation, characterization, in vitro and in vivo evaluation. Int J Pharm. 2014 Dec 30;477(1-2):399-407. doi: 10.1016/j.ijpharm.2014.10.055. Epub 2014 Oct 29. PMID: 25445521. 10: Hamilton G, Klameth L, Rath B, Thalhammer T. Synergism of cyclin-dependent kinase inhibitors with camptothecin derivatives in small cell lung cancer cell lines. Molecules. 2014 Feb 17;19(2):2077-88. doi: 10.3390/molecules19022077. PMID: 24549232; PMCID: PMC6271949. 11: Shukla RK. Recent advances in oral anticancer agents for colon cancer. Future Oncol. 2013 Dec;9(12):1893-908. doi: 10.2217/fon.13.137. PMID: 24295419. 12: Li D, Liang Y, Lai Y, Wang G, He B, Gu Z. Polymeric micelles with small lipophilic moieties for drug delivery. Colloids Surf B Biointerfaces. 2014 Apr 1;116:627-32. doi: 10.1016/j.colsurfb.2013.10.032. Epub 2013 Oct 30. PMID: 24268560. 13: Chen J, Hu RR, Yang XX, Gu W, Tian R, Gong F, Luo L, Fang F, Chen ZP, Cai BC. Antitumor efficacy, toxicity and pharmacokinetics of 9-nitrocamptothecin: role of lactone ratio. Cancer Chemother Pharmacol. 2013 Oct;72(4):925-9. doi: 10.1007/s00280-013-2259-x. Epub 2013 Aug 11. PMID: 23934323. 14: Saha SC, Patel D, Rahman S, Savva M. Physicochemical characterization, solubilization, and stabilization of 9-nitrocamptothecin using pluronic block copolymers. J Pharm Sci. 2013 Oct;102(10):3653-65. doi: 10.1002/jps.23671. Epub 2013 Jul 19. PMID: 23873658. 15: Xia M, Huang R, Sakamuru S, Alcorta D, Cho MH, Lee DH, Park DM, Kelley MJ, Sommer J, Austin CP. Identification of repurposed small molecule drugs for chordoma therapy. Cancer Biol Ther. 2013 Jul;14(7):638-47. doi: 10.4161/cbt.24596. Epub 2013 May 10. PMID: 23792643; PMCID: PMC3742493. 16: Cao Z, Mendoza J, Kozielski A, Liu X, Dejesus A, Wang Y, Zhan CG, Vardeman D, Giovanella B. Anticancer activity of new haloalkyl camptothecin esters against human cancer cell lines and human tumor xenografts grown in nude mice. Anticancer Agents Med Chem. 2012 Sep;12(7):818-28. doi: 10.2174/187152012802650219. PMID: 22583427. 17: Zheng S, Chang S, Lu J, Chen Z, Xie L, Nie Y, He B, Zou S, Gu Z. Characterization of 9-nitrocamptothecin liposomes: anticancer properties and mechanisms on hepatocellular carcinoma in vitro and in vivo. PLoS One. 2011;6(6):e21064. doi: 10.1371/journal.pone.0021064. Epub 2011 Jun 9. PMID: 21695227; PMCID: PMC3111480. 18: Jiang Y, Jiang X, Law K, Chen Y, Gu J, Zhang W, Xin H, Sha X, Fang X. Enhanced anti-tumor effect of 9-nitro-camptothecin complexed by hydroxypropyl-β- cyclodextrin and safety evaluation. Int J Pharm. 2011 Aug 30;415(1-2):252-8. doi: 10.1016/j.ijpharm.2011.05.056. Epub 2011 May 27. PMID: 21645594. 19: Ravivarapu H, Redkar S. Expect the unexpected-screen your screens. J Pharm Sci. 2011 May;100(5):1996. doi: 10.1002/jps.22424. Epub 2010 Dec 9. PMID: 21374629. 20: Yan Z, Zhu Z, Li K, Chen P, Wang L, Huang C, Xue J, Liu M. A phase I pharmacokinetics study of 9-nitrocamptothecin in patients with advanced solid tumors. Cancer Chemother Pharmacol. 2011 Apr;67(4):955-61. doi: 10.1007/s00280-010-1546-z. Epub 2010 Dec 30. PMID: 21191594.