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B5437

Sigma-Aldrich

Bendamustine hydrochloride hydrate

≥98% (HPLC)

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Synonym(s):
1H-Benzimidazole-2-butanoic acid, 5-[bis(2-chloroethyl)amino]-1-methyl monohydrochloride, Treanda
Empirical Formula (Hill Notation):
C16H21Cl2N3O2·HCl · xH2O
CAS Number:
1374784-02-7
Molecular Weight:
394.72 (anhydrous basis)
MDL number:
MFCD16879055
UNSPSC Code:
12352200
PubChem Substance ID:
329773260
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

off-white

solubility

H2O: >30 mg/mL

originator

Teva

storage temp.

room temp

SMILES string

O.Cl.Cn1c(CCCC(O)=O)nc2cc(ccc12)N(CCCl)CCCl

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

InChI key

TWBJYCLUHINEDN-UHFFFAOYSA-N

Related Categories

General description

Bendamustine comprises 2-chloroethylamine alkylating group, a butyric acid side chain and a benzimidazole ring in its structure and is a nitrogen mustard. It is catabolized in the liver by the enzyme cytochrome P450 1A2 into γ hydroxyl-bendamustine and N-desmethyl-bendamustine.

Application

Bendamustine hydrochloride hydrate has been used as:
  • a chemotherapy agent for chronic lymphocytic leukemia (CLL) samples to monitor spliced and unspliced gene expression
  • an inhibitor to E3 ubiquitin-protein ligase RNF3 (HOIP) in matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF) assay
  • a cytotoxic chemotherapeutic drug in high-throughput screening to test interaction with BAY87-2243

Biochem/physiol Actions

Bendamustine is a therapeutic agent employed in treating lymphomas and chronic lymphocytic leukemia. It may be useful in central nervous system (CNS) malignancies treatment regimen due to its penetration capacity into brain tissue. Bendamustine is a promising candidate for non-Hodgkin lymphoma and Hodgkin lymphoma therapies.
Bendamustine hydrochloride is a DNA-alkylator with a distinct pattern of activity. Bendamustine activates DNA-damage stress response and apoptosis; inhibits mitotic checkpoints; and induces mitotic catastrophe.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Teva. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H341,H351,H361fd

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2 - Muta. 2 - Repr. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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Sheridan M Hoy
Drugs, 72(14), 1929-1950 (2012-09-07)
Bendamustine (Levact®) is an alkylating agent consisting of three structural elements: a 2-chloroethylamine alkylating group; a butyric acid side chain; and a benzimidazole ring. Although its precise mechanism of action is as yet unknown, it appears to exert its antineoplastic
Therasa Kim et al.
BMC cancer, 18(1), 729-729 (2018-07-11)
A relatively high proportion of patients diagnosed with primary CNS lymphoma will experience recurrent disease, yet therapy options are limited in salvage therapy. This is the first study to evaluate a bendamustine-based combination regimen for the treatment of relapsed/refractory PCNSL
Elinor A Chapman et al.
Oncotarget, 8(61), 102948-102964 (2017-12-22)
The functional significance of AKT in chronic lymphocytic leukemia (CLL) remains unclear. Given the importance of non-malignant T cells in regulating clonal expansion in CLL, we investigated the role of AKT in T cell-mediated cytoprotection and proliferation using an established
Manoj K Kashyap et al.
Haematologica, 100(7), 945-954 (2015-04-12)
RNA splicing plays a fundamental role in human biology. Its relevance in cancer is rapidly emerging as demonstrated by spliceosome mutations that determine the prognosis of patients with hematologic malignancies. We report studies using FD-895 and pladienolide-B in primary leukemia
Optimal use of bendamustine in hematologic disorders: treatment recommendations from an international consensus panel-an update
Cheson BD, et al.
Leukemia Lymphoma, 57(4), 766-782 (2016)
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