Bendamustine HCl

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

Description:Bendamustine hydrochloride is the hydrochloride salt of bendamustine, a bifunctional mechlorethamine derivative with alkylator and antimetabolite activities. Bendamustine possesses three active moieties: an alkylating group; a benzimidazole ring, which may act as a purine analogue; and a butyric acid side chain. Although its exact mechanism of action is unknown, this agent appears to act primarily as an alkylator. Bendamustine metabolites alkylate and crosslink macromolecules, resulting in DNA, RNA and protein synthesis inhibition, and, subsequently, apoptosis.In October 2008, the FDA granted further approval to market Treanda for the treatment of indolent B-cell non-Hodgkin's lymphoma (NHL) that has progressed during or within six months of treatment with rituximab or a rituximab-containing regimen.

Price and Availability

Bendamustine HCl, purity > 98%, is in stock. The same day shipping out after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 200470Name: Bendamustine HClCAS#: 3543-75-7 (HCl)Chemical Formula: C16H22Cl3N3O2Exact Mass: Molecular Weight: 394.72Elemental Analysis:C, 48.68; H, 5.62; Cl, 26.95; N, 10.65; O, 8.11

Related CAS #:3543-75-7 (HCl)16506-27-7 (free base)

Synonym:SDX105; SDX 105; SDX-105; DD6304600; Bendamustine HCl; Bendamustine hydrochloride;Brand name: Treanda.

IUPAC/Chemical Name:4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid hydrochloride

InChi Key:ZHSKUOZOLHMKEA-UHFFFAOYSA-N

InChi Code:InChI=1S/C16H21Cl2N3O2.ClH/c1-20-14-6-5-12(21(9-7-17)10-8-18)11-13(14)19-15(20)3-2-4-16(22)23;/h5-6,11H,2-4,7-10H2,1H3,(H,22,23);1H

SMILES Code:O=C(O)CCCC1=NC2=CC(N(CCCl)CCCl)=CC=C2N1C.[H]Cl

Technical Data

Additional Information

According to http://en.wikipedia.org/wiki/Bendamustine, bendamustine was first synthesized in 1963 by Ozegowski and Krebs in East Germany (the former German Democratic Republic). It is a white, water soluble microcrystalline powder with amphoteric properties. Until 1990 it was available only in East Germany. East German investigators found that it was useful for treating chronic lymphocytic leukemia, HodgkinÂ’s disease, non-HodgkinÂ’s lymphoma, multiple myeloma and lung cancer. Bendamustine received its first marketing approval in Germany, which is marketed under the tradename Ribomustin, by Astellas Pharma GmbH"s licensee, Mundipharma International Corporation Limited, which it is indicated as a single-agent or in combination with other anti-cancer agents for indolent NHL, multiple myeloma, and CLL. SymBio Pharmaceuticals Ltd holds exclusive rights to develop and market bendamustine HCl in Japan and selected Asia Pacific Rim countries. In March 2008, Cephalon received approval from the United States Food and Drug Administration to market bendamustine in the US, where it is sold under the tradename Treanda, for treatment of CLL.  In October 2008, the FDA granted further approval to market Treanda for the treatment of indolent B-cell non-Hodgkin"s lymphoma (NHL) that has progressed during or within six months of treatment with rituximab or a rituximab-containing regimen.

References

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2: Gafter-Gvili A, Polliack A. Bendamustine associated immune suppression and infections during therapy of hematological malignancies. Leuk Lymphoma. 2016;57(3):512-9. doi: 10.3109/10428194.2015.1110748. Epub 2015 Dec 23. Review. PubMed PMID: 26696321.

3: Cheson BD, Brugger W, Damaj G, Dreyling M, Kahl B, Kimby E, Ogura M, WeidmannE, Wendtner CM, Zinzani PL. Optimal use of bendamustine in hematologic disorders: Treatment recommendations from an international consensus panel - an update. Leuk Lymphoma. 2016;57(4):766-82. doi: 10.3109/10428194.2015.1099647. Epub 2015 Nov 23. Review. PubMed PMID: 26592922; PubMed Central PMCID: PMC4840280.

4: Gentile M, Vigna E, Recchia AG, Morabito L, Mendicino F, Giagnuolo G, Morabito F. Bendamustine in multiple myeloma. Eur J Haematol. 2015 Nov;95(5):377-88. doi:10.1111/ejh.12609. Epub 2015 Jul 14. Review. PubMed PMID: 26085055.

5: Darwish M, Bond M, Hellriegel E, Robertson P Jr, Chovan JP. Pharmacokinetic and pharmacodynamic profile of bendamustine and its metabolites. Cancer Chemother Pharmacol. 2015 Jun;75(6):1143-54. doi: 10.1007/s00280-015-2727-6. Epub 2015 Apr1. Review. PubMed PMID: 25829094; PubMed Central PMCID: PMC4441746.

6: Kuno M, Inoue A, Aimoto M, Nakao T, Kameda K, Yoshida M, Kanashima H, Hirai M, Yamane T. [Alleviated anemia by bendamustine in cold agglutinin disease associated with small lymphocytic lymphoma]. Rinsho Ketsueki. 2015 Feb;56(2):204-9. doi: 10.11406/rinketsu.56.204. Review. Japanese. PubMed PMID: 25765801.

7: Palumbo A, Offidani M, Patriarca F, Petrucci MT, Cavo M. Bendamustine for thetreatment of multiple myeloma in first-line and relapsed-refractory settings: a review of clinical trial data. Leuk Lymphoma. 2015 Mar;56(3):559-67. doi: 10.3109/10428194.2014.915545. Epub 2014 Jun 27. Review. PubMed PMID: 24884319.

8: Haddad H, Mohammad F, Dai Q. Bendamustine-induced immune hemolytic anemia in a chronic lymphocytic leukemia patient: A case report and review of the literature. Hematol Oncol Stem Cell Ther. 2014 Dec;7(4):162-4. doi: 10.1016/j.hemonc.2014.04.001. Epub 2014 Apr 29. Review. PubMed PMID: 24785506.

9: Gil L, Kazmierczak M, Kroll-Balcerzak R, Komarnicki M. Bendamustine-based therapy as first-line treatment for non-Hodgkin lymphoma. Med Oncol. 2014 May;31(5):944. doi: 10.1007/s12032-014-0944-1. Epub 2014 Apr 22. Review. PubMed PMID: 24752517; PubMed Central PMCID: PMC4006123.

10: Ohmachi K, Maruyama D, Nisikori M, Suzuki T, Izutsu K. [Recommendation for the optimal use of bendamustine in Japan]. Rinsho Ketsueki. 2014 Mar;55(3):311-20. Review. PubMed PMID: 24681934.

11: Mitsumori T, Sueki Y, Kawashima I, Yamamoto T, Nozaki Y, Nakajima K, Kirito K. [Development of cytomegalovirus antigenemia in 3 patients with B cell lymphoma treated with bendamustine monotherapy]. Rinsho Ketsueki. 2014 Feb;55(2):239-43. Review. Japanese. PubMed PMID: 24598192.

12: Derenzini E, Zinzani PL, Cheson BD. Bendamustine: role and evidence in lymphoma therapy, an overview. Leuk Lymphoma. 2014 Jul;55(7):1471-8. doi: 10.3109/10428194.2013.842986. Epub 2014 Feb 4. Review. PubMed PMID: 24180334.

13: van der Jagt R. Bendamustine for indolent non-Hodgkin lymphoma in the front-line or relapsed setting: a review of pharmacokinetics and clinical trial outcomes. Expert Rev Hematol. 2013 Oct;6(5):525-37. doi: 10.1586/17474086.2013.841538. Review. PubMed PMID: 24125522.

14: Parker SM, Hyder MA, Fesler MJ. Bendamustine and rituximab for indolent B-cell non-hodgkin lymphoma in patients with compensated hepatitis C cirrhosis: a case series. Clin Lymphoma Myeloma Leuk. 2013 Dec;13(6):e15-7. doi: 10.1016/j.clml.2013.07.002. Epub 2013 Sep 20. Review. PubMed PMID: 24060287.

15: Gentile M, Recchia AG, Mazzone C, Vigna E, Martino M, Morabito L, Lucia E, Bossio S, De Stefano L, Granata T, Palummo A, Morabito F. An old drug with a newfuture: bendamustine in multiple myeloma. Expert Opin Pharmacother. 2013 Nov;14(16):2263-80. doi: 10.1517/14656566.2013.837885. Epub 2013 Sep 21. Review.PubMed PMID: 24053161.

16: Brugger W, Ghielmini M. Bendamustine in indolent non-Hodgkin"s lymphoma: a practice guide for patient management. Oncologist. 2013;18(8):954-64. doi: 10.1634/theoncologist.2013-0079. Epub 2013 Jul 30. Review. PubMed PMID: 23900001; PubMed Central PMCID: PMC3755934.

17: Ogura M. Rituximab plus bendamustine for the treatment of aggressive non-hodgkin lymphoma patients with severe liver impairment. Clin Adv Hematol Oncol. 2013 Mar;11(3):188-9. Review. PubMed PMID: 23598989.

18: Vidal L, Gafter-Gvili A, Gurion R, Raanani P, Dreyling M, Shpilberg O. Bendamustine for patients with indolent B cell lymphoid malignancies including chronic lymphocytic leukaemia. Cochrane Database Syst Rev. 2012 Sep 12;(9):CD009045. doi: 10.1002/14651858.CD009045.pub2. Review. PubMed PMID: 22972131.

19: Hoy SM. Bendamustine: a review of its use in the management of chronic lymphocytic leukaemia, rituximab-refractory indolent non-Hodgkin"s lymphoma and multiple myeloma. Drugs. 2012 Oct 1;72(14):1929-50. doi: 10.2165/11209510-000000000-00000. Review. PubMed PMID: 22950536.

20: Chang JE, Kahl BS. Bendamustine for treatment of chronic lymphocytic leukemia. Expert Opin Pharmacother. 2012 Jul;13(10):1495-505. doi: 10.1517/14656566.2012.693163. Epub 2012 Jun 5. Review. PubMed PMID: 22663160; PubMed Central PMCID: PMC3467097.