Bendamustine Hydrochloride Monohydrate Chemical Properties

InChI

InChI=1S/C16H21Cl2N3O2.ClH.H2O/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;1H2

InChIKey

TWBJYCLUHINEDN-UHFFFAOYSA-N

SMILES

CN1C(=NC2=CC(N(CCCl)CCCl)=CC=C12)CCCC(=O)O.Cl.O

Bendamustine Hydrochloride Monohydrate Usage And Synthesis

Structure

Commercial bendamustine hydrochloride monohydrate crystallizes in the monoclinic space group P21/c (14), with a = 4.71348(4) Å, b = 47.5325(3) Å, c = 8.97458 (5) Å, β = 96.6515(8)°, V = 1997.161(23) Å3, and Z = 4[1].

Uses

Bendamustine hydrochloride monohydrate (marketed as Treanda?) is a nitrogen mustard purine analog alkylator used to treat chronic lymphocytic leukemia (CLL) and non-Hodgkin lymphomas. Bendamustine is a nitrogen mustard drug used to treat chronic lymphocytic leukemia (CLL) and indolent B-cell non-Hodgkin lymphoma (NHL). Bendamustine is a bifunctional mechlorethamine derivative capable of forming electrophilic alkyl groups that covalently bond to other molecules. Through this function as an alkylating agent, bendamustine causes intra- and inter-strand crosslinks between DNA bases, resulting in cell death. It is active against both active and quiescent cells, although the exact mechanism of action is unknown.

References

[1] J. Kaduk. “Powder X-ray diffraction of bendamustine hydrochloride monohydrate, C16H22Cl2N3O2Cl·H2O.” Powder Diffraction 34 1 (2018): 74–75.