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CAS NO.3543-75-7
1(10-100)Metric Ton1(10-100)Metric Ton
| Bendamustine hydrochloride Basic information |
| Product Name: | Bendamustine hydrochloride |
| Synonyms: | bendamustine hydrochloride;BENDAMUSTIN HYDROCHLORIDE;CYTOSTASAN;1-methyl-5-bis(2-chloroethyl)amino-2-benzimidazolinebutryric acid hydrochloride;4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid hydrochloride;1-methyl-5-bis(2-chloroethyl)amino-2-benzimidazolinebutryricacihydrochlor;gamma(1-methyl-5-bis(beta-chloraethyl)aminobenzimidazoyl-2)buttersaeurehydro;BENDAMUSTINE HCL |
| CAS: | 3543-75-7 |
| MF: | C16H22Cl3N3O2 |
| MW: | 394.72 |
| EINECS: | |
| Product Categories: | API intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;API;Amines;Heterocycles;Ribomustin, Treanda, SDX-105 |
| Mol File: | 3543-75-7.mol |
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| Bendamustine hydrochloride Chemical Properties |
| mp | 149-151°C |
| storage temp. | Desiccate at RT |
| CAS DataBase Reference | 3543-75-7(CAS DataBase Reference) |
| Safety Information |
| Hazard Codes | T,Xn |
| Risk Statements | 60-61-22-40 |
| Safety Statements | 36-37 |
| Bendamustine hydrochloride Usage And Synthesis |
| 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. |
| Chemical Properties | Pale Brown Crystals |
| Usage | Used as an anticancer drug |
| Usage | Bendamustine HCL is a DNA-damaging agent with IC50 of 50 μM. |
| Usage | alkylating agent recently approved by the FDA for treatment of Chronic Lymphocytic Leukemia |
| Biological Activity | Cytostatic agent that displays activity in non-Hodgkin's lymphomas. Exhibits bifunctionality; combines DNA alkylating properties with those of purine analogs. |
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