Bendamustine

• CAS: 16506-27-7
• Catalog Number: ACM16506277
• Category: Main Products
• Molecular Weight: 358.26
• Molecular Formula: C₁₆H₂₁Cl₂N₃O₂
• Synonyms: 5-(Bis(2-chloroethyl)amino)-1-methyl-2-benzimidazolebutyric acid;5-[Bis(2-chloroethyl)amino]-1-methyl-1H-benzimidazole-2-butanoic acid;Bendamustine;4-(5-(bis(2-chloroethyl)aMino)-1-Methyl-1H-benzo[d]iMidazol-2-yl)butanoic acid;1H-BenziMidazole-2-butanoicacid, 5-[bis(2-chloroethyl)aMino]-1-Methyl-
• IUPAC Name: 4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoicacid
• Canonical SMILES: CN1C2=C(C=C(C=C2)N(CCCl)CCCl)N=C1CCCC(=O)O
• InChI Key: YTKUWDBFDASYHO-UHFFFAOYSA-N
• Boiling Point: 585.2ºC at 760 mmHg
• Density: 1.31 g/cm³
• Exact Mass: 357.10100

Case Study

Bendamustine is Used for the Treatment of Relapsed or Refractory Follicular Lymphoma

Flowers C. R, et al. Haematologica, 2024, 109(4), 1194-1205.

Bendamustine is a cornerstone in the treatment of relapsed or refractory (R/R) follicular lymphoma (FL), the most common subtype of indolent non-Hodgkin lymphoma. In the phase Ib/II GO29365 clinical trial, bendamustine was evaluated as part of combination regimens with polatuzumab vedotin and rituximab (Pola-BR) or obinutuzumab (Pola-BG) against a bendamustine-rituximab (BR) control arm. The study assessed efficacy, safety, and tolerability in 112 patients.
Bendamustine demonstrated significant antitumor activity across all treatment arms, with positron emission tomography complete response (PET-CR) rates of 63.4% (BR), 69.2% (Pola-BR), and 65.4% (Pola-BG). However, its combination with polatuzumab vedotin was associated with increased cytopenias and a higher frequency of serious adverse events compared to BR alone, indicating that the addition of polatuzumab did not enhance clinical outcomes meaningfully.
Bendamustine's unique bifunctional mechanism, combining alkylating and purine analog activity, underpins its efficacy in lymphoproliferative disorders, disrupting DNA replication and inducing apoptosis in malignant B cells. Despite its limitations in certain regimens, bendamustine remains a critical agent for R/R FL, offering a balance between effectiveness and manageable toxicity, particularly in combination therapies that exclude additional agents with overlapping toxicities.

Bendamustine: Effective Chemotherapy for Follicular Lymphoma in Reduced Cycles

Strouse C. S, et al. Blood Neoplasia, 2024, 1(3), 100019.

Bendamustine, a bifunctional alkylating agent, is a cornerstone in chemoimmunotherapy for follicular lymphoma (FL), particularly in elderly patients. Typically administered in 6-cycle regimens, recent evidence suggests that satisfactory therapeutic outcomes may be achievable with fewer cycles, thereby minimizing exposure-related toxicity. A study utilizing data from the National Cancer Institute (NCI) assessed the survival outcomes of FL patients treated with 3-4 versus 5-6 cycles of bendamustine. The analysis revealed that patients receiving fewer cycles were slightly older (mean age, 76.2 years) and had higher comorbidity scores (mean score, 2.0). Univariate analysis indicated a lower risk of death with 5-6 cycles (HR, 0.75; 95% CI, 0.57-0.98; P = .04); however, multivariate analysis controlling for age and comorbidities showed no significant difference in overall survival between the groups (HR, 0.87; 95% CI, 0.66-1.15; P =.33).

Bendamustine for the Treatment of Lymphoproliferative Neoplasms

Tageja, Nishant, et al. Cancer chemotherapy and pharmacology, 2010, 66, 413-423.

Bendamustine is a water-soluble bifunctional chemotherapeutic agent that also has potential antimetabolite properties and only partial cross-resistance with other alkylating agents. The research evaluated bendamustine treatment outcomes and toxicity results from lymphoproliferative tumor trials together with pharmacological studies along with pharmacokinetic and preclinical investigations. The key results are as follows:
· Bendamustine achieves remission in over 75% of patients with rituximab-refractory indolent B-cell non-Hodgkin lymphoma (NHL).
· When used in combination with rituximab in laboratory settings, bendamustine demonstrates synergistic effects against various leukemia and lymphoma cell lines.
· Clinical trials confirm that the bendamustine-rituximab combination is highly effective for patients with relapsed or refractory indolent lymphoma, resulting in remissions in 90% or more of cases, with a median progression-free survival of 23 to 24 months. It has been generally well tolerated in clinical settings, with a low likelihood of causing alopecia.
· The combination of bendamustine and rituximab could potentially establish a new standard first-line treatment for patients with follicular lymphoma (FL), mantle cell lymphoma (MCL), and other indolent lymphomas. Ongoing trials will further clarify the optimal use of bendamustine in indolent NHL.

Efficacy of Obinutuzumab Combined with Bendamustine in the Treatment of Non-Hodgkin's Lymphoma

Sehn, Laurie H., et al. The Lancet Oncology, 2016, 17(8), 1081-1093.

Patients with indolent non-Hodgkin lymphoma who do not achieve adequate disease control with rituximab-based therapies have limited treatment options and a bleak prognosis. This study aimed to evaluate the effectiveness of combining obinutuzumab (GA101) with bendamustine in this patient group. Results indicated that obinutuzumab combined with bendamustine, followed by obinutuzumab maintenance, shows better efficacy compared to bendamustine alone in rituximab-refractory patients, while also presenting manageable toxicity.
Efficacy of GA101 plus Bendamustine
· In a randomized trial of 396 patients (194 obinutuzumab plus bendamustine, 202 bendamustine monotherapy), after a median follow-up of 21.9 months and 20.3 months, respectively, progression-free survival was significantly longer in the combination arm (median not reached [95% CI 22.5 months-not estimable]) compared to bendamustine monotherapy (14.9 months [12.8-16.6]; HR 0.55 [95% CI 0.40-0.74]; p=0.0001).
· Grade 3-5 adverse events were similar between groups (68% vs 62%), with neutropenia, thrombocytopenia, anemia, and infusion-related reactions being most common. Serious adverse events occurred in 38% and 33% of patients, respectively, and treatment-related deaths were similar (6% in each group).

Custom Q&A

What is the molecular formula of bendamustine?

The molecular formula of bendamustine is C16H21Cl2N3O2.

What are some synonyms for bendamustine?

Some synonyms for bendamustine include Bendamustine [INN], Bendamustine free base, Bendamustinum [Latin], and Treanda (TN).

What is the IUPAC name of bendamustine?

The IUPAC name of bendamustine is 4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid.

What is the InChIKey of bendamustine?

The InChIKey of bendamustine is YTKUWDBFDASYHO-UHFFFAOYSA-N.

What is the common trade name for bendamustine?

The common trade name for bendamustine is Treanda.

What is the chemical structure of bendamustine?

The chemical structure of bendamustine can be found in the reference.

What is the CAS number of bendamustine?

The CAS number of bendamustine is 16506-27-7.

Is bendamustine considered a health hazard?

Yes, bendamustine is considered a health hazard.

What is the chemical formula of bendamustine in 2D representation?

The chemical formula of bendamustine in 2D representation can be found in the reference.

What are some other identifiers for bendamustine?

Some other identifiers for bendamustine include NIOSH/DD6304600, HSDB 7763, and DTXSID2046888.