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ChemicalBook >> CAS DataBase List >>Bendamustine hydrochloride

Bendamustine hydrochloride

CAS No.
3543-75-7
Chemical Name:
Bendamustine hydrochloride
Synonyms
EP3101;Treanda;SDX 105;DD6304600;CYTOSTASAN;Ribomustin;ZIMET-33/93;Cytostasane;Bendamustina;CytostasanHCl
CBNumber:
CB0777896
Molecular Formula:
C16H22Cl3N3O2
Molecular Weight:
394.72
MDL Number:
MFCD01658758
MOL File:
3543-75-7.mol
Last updated:2024-10-30 18:52:02

Bendamustine hydrochloride Properties

Melting point 149-151°C
storage temp. room temp
solubility H2O: >30mg/mL
form powder
color off-white
Merck 14,1034
InChIKey ZHSKUOZOLHMKEA-UHFFFAOYSA-N
CAS DataBase Reference 3543-75-7(CAS DataBase Reference)
NCI Dictionary of Cancer Terms bendamustine hydrochloride; Treanda
FDA UNII 981Y8SX18M
NCI Drug Dictionary bendamustine hydrochloride

Pharmacokinetic data

Protein binding >95%
Excreted unchanged in urine 3 (20% as unchanged drug and metabolites)
Volume of distribution 15.8-20.5 Litres
Biological half-life 28.2 minutes / -

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Signal word  Danger
Hazard statements  H301-H341-H351-H361fd
Hazard statements  H301-H341-H351-H361fd
Precautionary statements  P201-P202-P264-P270-P280-P301+P310
Precautionary statements  P201-P202-P264-P270-P280-P301+P310
Hazard Codes  T,Xn
Risk Statements  60-61-22-40
Safety Statements  36-37
RIDADR  UN 2811 6.1 / PGIII
WGK Germany  3
RTECS  DE1590000
HazardClass  6.1
PackingGroup  III
HS Code  29339900
Toxicity LD50 (monohydrate) in mice, rats (mg/kg): 400-500, 200-300 orally; 80, 40 i.v. (Horn)
NFPA 704
0
2 0

Bendamustine hydrochloride price More Price(39)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich B5437 Bendamustine hydrochloride hydrate ≥98% (HPLC) 3543-75-7 5mg $91.8 2024-03-01 Buy
Sigma-Aldrich B5437 Bendamustine hydrochloride hydrate ≥98% (HPLC) 3543-75-7 25mg $241.6 2024-03-01 Buy
TCI Chemical B4033 Bendamustine Hydrochloride Hydrate >98.0%(HPLC)(T) 3543-75-7 200mg $186 2021-12-16 Buy
Cayman Chemical 23693 Bendamustine (hydrochloride) ≥98% 3543-75-7 25mg $68 2024-03-01 Buy
Cayman Chemical 23693 Bendamustine (hydrochloride) ≥98% 3543-75-7 50mg $121 2024-03-01 Buy
Product number Packaging Price Buy
B5437 5mg $91.8 Buy
B5437 25mg $241.6 Buy
B4033 200mg $186 Buy
23693 25mg $68 Buy
23693 50mg $121 Buy

Bendamustine hydrochloride Chemical Properties,Uses,Production

Product description

Bendamustine hydrochloride was first successfully developed in the early 1860s by the Ozegowski and his colleagues in the “Microbiology Experiment Association (Jena in Germany)”. The original purpose of developing it is intended to make a kind of alkylated chloremethine (a non-effective alkylating agent) be connected to a purine and amino acids. Compared with the chlorambucil, the main advantage of the newly synthesized compound is its water solubility. It was then widely applied. However, it is not until the end of the Cold War before the drug had been applied in Europe to clinical studies in either a number of single medication or in combination with other drugs for treating various kinds of blood malignancies and non-Hodgkin's lymphoma, multiple myeloma, CLL and breast cancer and some other solid tumors. The efficacy is very impressive. The drug had significantly reduced the recurrence rate and death rate with small adverse reactions and good security. So far, the clinical protocols of both monotherapy and combination therapy of bendamustine hydrochloride has been designated as either first-or second-line treatment option for treating various kinds of hematological malignancies by Europe and America clinical guidelines.
From 1971 to 1992, Bendamustine was sold by the Jena pharmaceutical companies in the trade name of “Cytostasan”. From 1993, the cell growth inhibitor entered into market with the trade name “Ribomustine” mediated by Ribosepharm Company.
In 2003, the bendamustine hydrochloride product developed by German Ribosepharm Company entered into market in Germany with the trade name "Ribomustin".
In 2008, the Bendamustine hydrochloride injection product developed by the United States Cephalon Company entered into market in United States under the trade name “Treanda” which is used for the treatment of the relapsed and refractory B-cell non-Hodgkin’s lymphoma which is failed be to be treated rituximab monotherapy.

Indications

In March 2008, the US Food and Drug Authority (briefly called FDA) first approved bendamustine hydrochloride for the treatment of chronic lymphocytic leukemia (CLL). In October of the same year, FDA had approved for the second indication of the drug: the indolent B-cell non-Hodgkin's lymphoma (NHL) patients who have their symptoms still be in progress during the treatment with either rituximab or rituximab-containing regimen or within 6 months of the treatment.

The dose and medication

The lyophilized powder of bendamustine is white to off-white. Its specification is 100mg/tube. This storage temperature of this medicine should not exceed 30 ℃ and should be protected from light and should be temporarily prepared before use.
Preparation process: Every 100 mg of the drug must be first dissolved in 20ml of sterile water (for injection), fully shake until completely dissolve it into a clear, colorless or pale yellow solution with dissolution time generally being not more than 5 minutes and the final dissolving concentration being 5mg/ml. Within 30 minutes after the dissolution, extract certain amount of bendamustine solution according to the necessity, transfer it to a 500ml Sodium Chloride Injection (0.9%) or glucose-sodium chloride injection (2.5%/0.45%), and make sure the final concentration of benzene bendamustine in injection be between 0.2~0.6mg/ml. The prepared injection can be kept refrigerated for 24 hours at 2~8 ℃, or stored for 3 hours at room temperature and natural light.
Upon the treatment of chronic lymphocytic leukemia, take 28-day as one treatment cycle. It normally takes six treatment cycles. Drugs should be administered at the first day and the second day of each cycle of treatment; the recommended dose is 100mg/m2. The drug is administered through intravenous infusion with each administration time being no less than 30 minutes.
Upon treatment of indolent B-cell non-Hodgkin's lymphoma, take 21-day as one treatment cycle. It normally takes eight treatment cycles. The drugs should be administered at the first day and the second day of each cycle of treatment with the recommended dose being 120 mg/m2 and each administration time being no less than 60 minutes.

Pharmacological effects

The exact mechanism of action of bendamustine hydrochloride is not yet clear. But it is already known that the drug is a carry a chloremethine derivative carrying a purine-like benzimidazole ring with dual mechanisms of action of both alkylating agents and purine analogs (anti-metabolite). Bendamustine hydrochloride can cause cell death through several different pathways and is effective in treating both division cells as well as stationary phase cells.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Pharmacokinetics

The plasma protein binding rate of bendamustine hydrochloride should be 94% to 96%. Data has shown that this drug is generally not mutually substitutable with other protein bound drugs. The mean steady-state volume of distribution of bendamustine hydrochloride is approximately 25L. Its whole blood/plasma concentration ratio is 0.84 to 0.86. Bendamustine hydrochloride is mainly metabolized through hydrolysis while forming low-cytotoxic metabolites. The drug can be converted to two active metabolites, M3 and M4 via CYP1A2 metabolic pathway. But the plasma concentrations of both the two metabolites only correspond to 1/10 and 1/100, respectively of the parent compound, and therefore, it can be speculated that the cytotoxic effect of bendamustine mainly orginiates from itself instead of its metabolites.

Contraindications

Patients who are allergic to Bendamustine hydrochloride and mannitol should be disabled for using it.

Drug Interactions

When used in combination with the CYP1A2 inhibitors (e.g. fluvoxamine, ciprofloxacin), it may increase blood concentrations of bendamustine while causing the decrease of the concentration of its metabolites M3 and M4.
When used in combination with CYP1A2 inducers (such as omeprazole, smoking, etc.), it may reduce the blood concentration of bendamustine while increasing the concentration of it metabolites M3 and M4.

Adverse reactions and side effects

Common adverse reactions include nausea, vomiting, diarrhea, fatigue, weakness, skin rashes, itching, some kinds of infection symptoms and body signs (such as persistent sore throat, fever and chills), easy for bruising/bleeding and ulcers in the mouth; in some serious adverse reactions, there may be bone marrow suppression and tumor lysis syndrome.
It may cause mild or severe allergic reaction. During the process of administration or the early phase of post-administration, there may be some allergic symptoms such as rash, facial swelling, and difficulty in breathing.
It may negatively affect the fetus, so women who are during treatment and within three months after treatment should take appropriate contraceptive measures as well as stop breast-feeding.

Description

Bendamustine is a purine analog and DNA alkylating agent. It inhibits growth of SKW-3, Reh, CML-T1, BV-173, and HL-60 leukemia cell lines (IC50s = 27.0, 28.6, 15.6, 20.8, and 57.7 μM, respectively) but not MCF-7 and MDA-MB-231 breast cancer cell lines (IC50s = >200 and >200 μM, respectively). It kills B cell-chronic lymphocytic leukemia (B-CLL) cells derived from naïve and bendamustine-pretreated patients (LD50s = 6.8-8.3 and 3.8-4.9 mg/ml, respectively). Bendamustine (50 mg/kg) inhibits tumor growth by 9% and 96% alone and in combination with ofatumumab, respectively, in a JVM-3 CLL mouse xenograft model. It activates the DNA-damage stress response, the base excision DNA repair pathway, and apoptosis, as well as inhibits mitotic checkpoints and induces mitotic catastrophe. Formulations containing bendamustine have been used to treat CLL and non-Hodgkin lymphoma.

Chemical Properties

Pale Brown Crystals

Uses

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

Uses

Bendamustine HCL is a DNA-damaging agent with IC50 of 50 μM.

Uses

Used as an anticancer drug

Uses

alkylating agent recently approved by the FDA for treatment of Chronic Lymphocytic Leukemia

brand name

Ribomustine (Amcis AG, Switzerland).

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.

Biological Activity

Cytostatic agent that displays activity in non-Hodgkin's lymphomas. Exhibits bifunctionality; combines DNA alkylating properties with those of purine analogs.

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.

Clinical Use

Alkylating agent:

CLL, NHL and multiple myeloma

Drug interactions

Potentially hazardous interactions with other drugs
Antipsychotics: avoid with clozapine (increased risk of agranulocytosis).

Metabolism

A major route of clearance of bendamustine is the hydrolysis to monohydroxy- and dihydroxybendamustine. Formation of N-desmethyl-bendamustine and gamma-hydroxy-bendamustine by hepatic metabolism involves cytochrome P450 (CYP) 1A2 isoenzyme. Another major route of bendamustine metabolism involves conjugation with glutathione. Excreted in the urine and faeces as unchanged drug and metabolites.

storage

Desiccate at RT

References

[1]. leoni lm, bailey b, reifert j, bendall hh, zeller rw, corbeil j, elliott g, niemeyer cc. bendamustine (treanda) displays a distinct pattern of cytotoxicity and unique mechanistic features compared with other alkylating agents. clin cancer res. 2008 jan 1;14(1):309-17.
[2]. gaul l, mandl-weber s, baumann p, emmerich b, schmidmaier r. bendamustine induces g2 cell cycle arrest and apoptosis in myeloma cells: the role of atm-chk2-cdc25a and atm-p53-p21-pathways. j cancer res clin oncol. 2008 feb;134(2):245-53.
[3]. roué g, lópez-guerra m, milpied p, pérez-galán p, villamor n, montserrat e, campo e, colomer d. bendamustine is effective in p53-deficient b-cell neoplasms and requires oxidative stress and caspase-independent signaling. clin cancer res. 2008 nov 1;14(21):6907-15.
[4]. cai b, wang s, huang j, lee ck, gao c, liu b. cladribine and bendamustine exhibit inhibitory activity in dexamethasone-sensitive and -resistant multiple myeloma cells. am j transl res. 2013;5(1):36-46.

3543-74-6
3543-75-7
Synthesis of Bendamustine hydrochloride from 5-[Bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazole-2-butanoic acid ethyl ester
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