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MedKoo product information:

 

Berubicin

 

Description of berubicin: berubicin hydrochloride is the hydrochloride salt of the anthracycline derivative berubicin with potential antineoplastic activity. Berubicin intercalates into DNA and interrupts topoisomerase II activity, resulting in the inhibition of DNA replication and repair, and RNA and protein synthesis. Unlike other anthracycline derivatives, this agent crosses the blood-brain barrier (BBB). Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

 

Current developer:    Reata Pharmaceuticals Inc.

  

MedKoo Code#:  200490

Name:  Berubicin

CAS#:  677017-23-1(Berubicin ), 293736-67-1 (Berubicin hydrochloride)

  

Synonym:   RTA 744. Code name: RTA 744.  WP 769.

  

IUPAC/Chemical name: 

(8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride

  

Chemical structure Theoretical analysis

 

 

 

Berubicin

Chemical Formula: C34H35NO11

Exact Mass: 633.22101

Molecular Weight: 633.64

Elemental Analysis: C, 64.45; H, 5.57; N, 2.21; O, 27.77

 

Berubicin hydrochloride

Chemical Formula: C34H36ClNO11

Molecular Weight: 670.10

Elemental Analysis: C, 60.94; H, 5.41; Cl, 5.29; N, 2.09; O, 26.26

  

  

Availability and price:

 

This agent is not in stock, which may be available through custom synthesis.

 

To inquire quotation and lead time or to ask questions, please send email to sales@medkoo.com to describe your needs. A representative will respond your email shortly. We offer big discount for orders of bulk quantities.

 

Quality control data:

Product will be shipped with supporting analytical data.

 

 

Information about this agent

Berubicin belongs to a novel class of anthracycline derivatives that cross the blood-brain barrier and show significant potential for the treatment of primary and secondary brain cancers. While other drugs in this class (for example, doxorubicin) are some of the most broadly used and effective cancer therapies, they do not cross the blood-brain barrier and are not effective in treating brain tumors. These compounds are potent inhibitors of topoisomerase II, a DNA repair enzyme. Overexpression of topo II has been identified as an indicator of aggressive cell proliferation and a negative prognostic indicator in patients with primary brain cancers. Topo II inhibition is likely to be effective in combination with temozolomide, the current standard therapy in glioblastoma.  see http://www.reatapharma.com/pip_rta744.asp.

 

References

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2. Wang, Yaolin; Wang, Yan; Lu, Brian Der-Hua; Liu, Ming; Seidel-Dugan, Cynthia; Yao, Siu-Long. Sequential administration of chemotherapeutic agents and anti-(insulin-like growth factor 1 receptor) for treatment of cancer. PCT Int. Appl. (2009), 104 pp. CODEN: PIXXD2 WO 2009137378 A2 20091112 CAN 151:521177 AN 2009:1395230

3. Zabudkin, Alexander; Matvienko, Victor; Matveev, Alexey; Itkin, Aleksandr. Process of aralkylation of the 4'-hydroxyl group in anthracyclins. PCT Int. Appl. (2009), 14pp.; Chemical Indexing Equivalent to 151:124315 (US). CODEN: PIXXD2 WO 2009088618 A1 20090716 CAN 151:148572 AN 2009:859254

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5. Wang, Yan; Wang, Yaolin; Levitan, Diane; Seidel-Dugan, Cynthia; Liu, Ming; Ding, Wei. Gene expression biomarkers for detecting IGF1R inhibitor-resistant or -sensitive cancers and uses in anti-IGF1R antibody combination chemotherapy. PCT Int. Appl. (2009), 165pp. CODEN: PIXXD2 WO 2009079587 A2 20090625 CAN 151:116583 AN 2009:769153

6. Ramachandra, Sumant; Bishop, Robert Walter; Masat, Linda; Huang, Chao Bai; Takeuchi, Toshihiko; Kantak, Seema. Human anti-VEGF antibodies and conjugates for treatment of angiogenesis conditions. PCT Int. Appl. (2009), 195pp. CODEN: PIXXD2 WO 2009055343 A2 20090430 CAN 150:492909 AN 2009:519479

7. Wang, Yan; Pachter, Jonathan A.; Hailey, Judith Anne; Brams, Peter; Williams, Denise; Srinivasan, Mohan; Feingersh, Mary Diane. Anti-insulin-like growth factor 1 receptor therapy. PCT Int. Appl. (2009), 129pp. CODEN: PIXXD2 WO 2009005673 A1 20090108 CAN 150:119716 AN 2009:25215

8. Wang, Yan; Zong, Chen; Seidel-Dugan, Cynthia; Wang, Yaolin; Yao, Siu-Long; Lu, Brian Der-Hua; Ladha, Mohamed H. Methods of treating cancer using IGF1R inhibitors. PCT Int. Appl. (2008), 103pp. CODEN: PIXXD2 WO 2008076278 A2 20080626 CAN 149:102715 AN 2008:771165

9. Szeja, Wieslaw. Method of producing anthracycline glycoside derivatives via regioselective alkylation reaction as prodrug antibacterial and antitumor agents. PCT Int. Appl. (2008), 35pp. CODEN: PIXXD2 WO 2008029294 A2 20080313 CAN 148:331949 AN 2008:322136

10. Wang, Yan. Blood levels of insulin-like growth factor-binding protein 2 as a marker for monitoring the effectiveness of inhibitors of insulin-like growth factor I receptors in cancer therapy. PCT Int. Appl. (2008), 133pp. CODEN: PIXXD2 WO 2008005469 A2 20080110 CAN 148:135980 AN 2008:43490

11. Meyer, Colin. Combination of chemotherapeutic compounds for treating cancer. PCT Int. Appl. (2007), 56pp. CODEN: PIXXD2 WO 2007139556 A1 20071206 CAN 148:24399 AN 2007:1391264

12. Brooks, Tracy A.; O'Loughlin, Kieran L.; Minderman, Hans; Bundy, Brian N.; Ford, Laurie A.; Vredenburg, Michael R.; Bernacki, Ralph J.; Priebe, Waldemar; Baer, Maria R. The 4'-O-benzylated doxorubicin analog WP744 overcomes resistance mediated by P-glycoprotein, multidrug resistance protein and breast cancer resistance protein in cell lines and acute myeloid leukemia cells. Investigational New Drugs (2007), 25(2), 115-122. CODEN: INNDDK ISSN:0167-6997. CAN 146:265997 AN 2006:1347370

13. Chlopkiewicz, Bozena; Ejchart, Anna; Marczewska, Jadwiga; Anuszewska, Elzbieta; Priebe, Waldemar. Evaluation of mutagenic and genotoxic activities of new derivatives of anthracyclines. Acta Poloniae Pharmaceutica (2005), 62(2), 99-104. CODEN: APPHAX ISSN:0001-6837. CAN 144:266685 AN 2005:1019481

14. Wu, Jianqiang; Harris, Nathaniel L.; Inge, Thomas H. Nuclear factor-kappa B and apoptosis inducing factor activation by doxorubicin analog WP744 in SH-SY5Y neuroblastoma cells. Journal of Surgical Research (2004), 122(2), 231-239. CODEN: JSGRA2 ISSN:0022-4804. CAN 142:273535 AN 2004:1004383

15. Trevino, Alex V.; Woynarowska, Barbara A.; Herman, Terence S.; Priebe, Waldemar; Woynarowski, Jan M. Enhanced topoisomerase II targeting by annamycin and related 4-demethoxy anthracycline analogues. Molecular Cancer Therapeutics (2004), 3(11), 1403-1410. CODEN: MCTOCF ISSN:1535-7163. CAN 142:232590 AN 2004:974751

16. Inge, Thomas H.; Harris, Nathaniel L.; Wu, Jianqiang; Azizkhan, Richard G.; Priebe, Waldemar. WP744 is a novel anthracycline with enhanced activity against neuroblastoma. Journal of Surgical Research (2004), 121(2), 187-196. CODEN: JSGRA2 ISSN:0022-4804. CAN 142:232319 AN 2004:888897

17. Ashikawa, Kazuhiro; Shishodia, Shishir; Fokt, Izabel; Priebe, Waldemar; Aggarwal, Bharat B. Evidence that activation of nuclear factor- B is essential for the cytotoxic effects of doxorubicin and its analogues. Biochemical Pharmacology (2004), 67(2), 353-364. CODEN: BCPCA6 ISSN:0006-2952. CAN 140:210149 AN 2003:999931

18. Salerno, Milena; Przewloka, Teresa; Fokt, Izabela; Priebe, Waldemar; Garnier-Suillerot, Arlette. Preferential efflux by P-glycoprotein, but not MRP1, of compounds containing a free electron donor amine. Biochemical Pharmacology (2002), 63(8), 1471-1479. CODEN: BCPCA6 ISSN:0006-2952. CAN 138:117233 AN 2002:340722

19. Faderl, Stefan; Estrov, Zeev; Kantarjian, Hagop M.; Harris, David; Van, Quin; Fokt, Izabela; Przewloka, Teresa; Godlewski, Christopher; Woynarowski, Jan M.; Priebe, Waldemar. WP744, a novel anthracycline with enhanced proapoptotic and antileukemic activity. Anticancer Research (2001), 21(6A), 3777-3784. CODEN: ANTRD4 ISSN:0250-7005. CAN 137:272864 AN 2002:262828

20. Priebe, Waldemar; Fokt, Izabela; Przewloka, Teresa; Krawczyk, Marta; Skibicki, Piotr; Grynkiewicz, Gregorz; Perez-Soler, Roman. Methods and compositions for the manufacture of C-3' and C-4' anthracycline glycoside antibiotics. PCT Int. Appl. (2000), 119 pp. CODEN: PIXXD2 WO 2000056267 A2 20000928 CAN 133:238250 AN 2000:688030

21. Rudnicki, Witold R.; Kurzepa, Malgorzata; Szczepanik, Teresa; Priebe, Waldemar; Lesyng, Bogdan. A simple model for predicting the free energy of binding between anthracycline antibiotics and DNA. Acta Biochimica Polonica (2000), 47(1), 1-9. CODEN: ABPLAF ISSN:0001-527X. CAN 134:39118 AN 2000:407815

 

 

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