Basic information
- Standard SMILES
Cl.Cn1c(CCCC(=O)O)nc2cc(N(CCCl)CCCl)ccc21- InChIKey
ZHSKUOZOLHMKEA-UHFFFAOYSA-N- Molecular formula
- C16H22Cl3N3O2
- Average molar mass
- 394.7 g/mol
- Monoisotopic mass
- 393.07775998
Overview
Bendamustine Hydrochloride is the hydrochloride salt of bendamustine, a bifunctional mechlorethamine derivative with alkylator and antimetabolite activities. Bendamustine possesses three active moieties: an alkylating group; a benzimidazole ring, which may act as a purine analogue; and a butyric acid side chain. Although its exact mechanism of action is unknown this agent appears to act primarily as an alkylator. Bendamustine metabolites alkylate and crosslink macromolecules, resulting in DNA, RNA and protein synthesis inhibition, and, subsequently, apoptosis. Bendamustine may differ from other alkylators in that it may be more potent in activating p53-dependent stress pathways and inducing apoptosis; it may induce mitotic catastrophe; and it may activate a base excision DNA repair pathway rather than an alkyltransferase DNA repair mechanism. Accordingly, this agent may be more efficacious and less susceptible to drug resistance than other alkylators.
Names & identifiers
- Preferred name
- Bendamustine Hydrochloride
- IUPAC
- 4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid;hydrochloride
- English name
- Bendamustine hydrochloride
- Molecular formula
- C16H22Cl3N3O2
- Molecular weight
- 394.72
Names & synonyms
Bendamustine hydrochloride3543-75-7Bendamustine HClTreandaRibomustinBendamustin hydrochlorideBendekaRibomustineSyB L-0501VIVIMUSTALevactNSC-138783
Show more names
BendaMustine hydrochloride hydrateEP3101SDX 105DD6304600CYTOSTASANZIMET-33/93Cytostasane
SYBL-0501981Y8SX18MDTXSID40188912NSC1387831H-Benzimidazole-2-butanoic acid, 5-(bis(2-chloroethyl)amino)-1-methyl-, monohydrochloride2-Benzimidazolinebutryric acid, 1-methyl-5-bis(2-chloroethyl)amino-, hydrochloridebendamustinBelrapzo
Database identifiers
- CAS
3543-75-7- PubChem CID
- 77082
- DTXSID
DTXSID40188912- ChEMBL
CHEMBL1201734- UNII
- 981Y8SX18M
- EC Number
- 631-540-0
Properties
Computed structural properties
- Topological polar surface area
- 58.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 380
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Antineoplastic Agents, Alkylating; Nitrosourea Compounds
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 149 · 149-151°C
- storage temp.
- room temp
- solubility
- 2 O: · H2O: >30mg/mL
- form
- powder
- color
- off-white
- Merck
- 14 · 14,1034
- Major Application
- (Pharmaceutical small molecule)
- InChI
- InChI=1S/C16H21Cl2N3O2.ClH/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
- InChIKey
- ZHSKUOZOLHMKEA-UHFFFAOYSA-N
- SMILES
- C12N=C(CCCC(=O)O)N(C)C=1C=CC(N(CCCl)CCCl)=C2.Cl
- CAS DataBase Reference
- 3543 · 3543-75-7(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- bendamustine hydrochloride; Treanda
- FDA UNII
- 981 Y8SX18M · 981Y8SX18M
- NCI Drug Dictionary
- bendamustine hydrochloride
- NACRES
- 24 · NA.24
- Protein binding
- 95 % · >95%
- Excreted unchanged in urine
- 3 · 3 (20% as unchanged drug and metabolites)
- Volume of distribution
- 15.8 · 15.8-20.5 Litres
- Biological half-life
- 28.2 minutes · 28.2 minutes / -
- Symbol(GHS)
- 6 · GHS06,GHS08
- Signal word
- Danger
- Hazard statements
- 301 · H301-H341-H351-H361fd
- Precautionary statements
- 201 · P201-P202-P264-P270-P280-P301+P310
- Hazard Codes
- T,Xn
- Risk Statements
- 60 · 60-61-22-40
- Safety Statements
- 36 · 36-37
- RIDADR
- 2811 · UN 2811 6.1 / PGIII
- WGK Germany
- 3 · 3
- RTECS
- 1590000 · DE1590000
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29339900 · 29339900
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 OralCarc · Acute Tox. 3 OralCarc. 2Muta. 2Repr. 2
- Toxicity
- 50 · LD50 (monohydrate) in mice, rats (mg/kg): 400-500, 200-300 orally; 80, 40 i.v. (Horn)
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (95.9%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (95.9%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Bendamustine hydrochloride
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 3
- rtecs
- DE1590000
- ridadr
- UN 2811 6.1 / PGIII
- hs_code
- 29339900
- Toxicity
- LD50 (monohydrate) in mice, rats (mg/kg): 400-500, 200-300 orally; 80, 40 i.v. (Horn)
- risk_code
- 60-61-22-40
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- T,Xn
- safety_code
- 36-37
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301-H341-H351-H361fd
- Hazard Classifications
- Acute Tox. 3 OralCarc. 2Muta. 2Repr. 2
- Precautionary statements
- P201-P202-P264-P270-P280-P301+P310
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
BENDAMUSTINE HCL
Alkylating Drug [EPC]; Alkylating Activity [MoA]
BENDAMUSTINE HYDROCHLORIDE
Alkylating Drug [EPC]; Alkylating Activity [MoA]
MeSH Pharmacological Classification
A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026)
Applications
DescriptionBendamustine 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.
UsesUsed as an anticancer drug
UsesBendamustine HCL is a DNA-damaging agent with IC50 of 50 μM.
Usesalkylating agent recently approved by the FDA for treatment of Chronic Lymphocytic Leukemia
UsesBendamustine 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) inmatrix-assisted laser desorption ionization time-of-flight mass spectrometry(MALDI-TOF) assaya cytotoxic chemotherapeutic drug in high-throughput screening to test interaction with BAY87-2243
General DescriptionBendamustine 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.
Upstream & downstream products
Upstream raw materials
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北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
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LGM Pharma1-(800)-881-8210 · [email protected]
Syntechem Co.,Ltd[email protected]
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