Bendamustine Hydrochloride (HCID 77082)

概要

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.

名称と識別子

優先名称: Bendamustine Hydrochloride
IUPAC: 4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid;hydrochloride
現地名: ベンダムスチン塩酸塩
英語名: Bendamustine hydrochloride
分子式: C16H22Cl3N3O2
分子量: 394.72

名称と別名

Bendamustine hydrochloride3543-75-7Bendamustine HClTreandaRibomustinBendamustin hydrochlorideBendekaRibomustineSyB L-0501VIVIMUSTALevactNSC-138783

名称をさらに表示

ベンダムスチン塩酸塩4-[5-[ビス(2-クロロエチル)アミノ]-1-メチル-1H-ベンゾイミダゾール-2-イル]酪酸·塩酸塩シトスタサン4-[1-メチル-5-[ビス(2-クロロエチル)アミノ]-1H-ベンゾイミダゾール-2-イル]酪酸·塩酸塩塩酸ベンダムスチンベンダムスチン塩酸塩水和物5-[ビス(2-クロロエチル)アミノ]-1-メチルベンゾイミダゾール-2-酪酸塩酸塩水和物ベンダマスチン塩酸塩 HYDRATEベンダマスチン塩酸塩ベンダムスチン塩酸塩水和物ベンダムスチン塩酸塩 (JAN)4-[5-[ビス(2-クロロエチル)アミノ]-1-メチル-1H-ベンゾイミダゾール-2-イル]ブタン酸・塩酸塩4-[1-メチル-5-[ビス(2-クロロエチル)アミノ]-1H-ベンゾイミダゾール-2-イル]酪酸・塩酸塩ベンダムスチン・塩酸塩トレアキシン4-[5-[ビス(2-クロロエチル)アミノ]-1-メチル-1H-ベンゾイミダゾール-2-イル]酪酸・塩酸塩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

データベース識別子

CAS: 3543-75-7
PubChem CID: 77082
DTXSID: DTXSID40188912
ChEMBL: CHEMBL1201734
UNII: 981Y8SX18M
EC Number: 631-540-0

物性

構造計算による物性

極性表面積: 58.4 Å²
水素結合供与体数: 2
水素結合受容体数: 4
回転可能結合数: 9
重原子数: 24
形式電荷: 0
複雑度: 380

実験および物理化学的性質

Human Drugs · 3 件

Breast Feeding; Lactation; Antineoplastic Agents, Alkylating; Nitrosourea Compounds

FDA approved drugs -> Active ingredient

物理化学的性質

融点: 149 · 149-151°C
貯蔵温度: room temp
溶解性: 2 O: · H2O: >30mg/mL
外見: 粉
色: オフホワイト
Merck: 14 · 14,1034
主な用途: （医薬品低分子化合物）
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 データベース: 3543 · 3543-75-7(CAS DataBase Reference)

化学的性質

化学的特性Pale Brown Crystals

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 3 (95.9%)

毒性情報

Drug Induced Liver Injury · 6 件

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

安全データ

wgk: 3
rtecs: DE1590000
ridadr: UN 2811 6.1 / PGIII
毒性: LD50 (monohydrate) in mice, rats (mg/kg): 400-500, 200-300 orally; 80, 40 i.v. (Horn)
hs_code: 29339900
risk_code: 60-61-22-40
hazard_code: T,Xn
safety_code: 36-37
hazard_class: 6.1
packing_group: III
Hazard Classifications: Acute Tox. 3 OralCarc. 2Muta. 2Repr. 2
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

薬理情報

FDA Pharmacological Classification · 4 件

BENDAMUSTINE HCL

Alkylating Drug [EPC]; Alkylating Activity [MoA]

BENDAMUSTINE HYDROCHLORIDE

Alkylating Drug [EPC]; Alkylating Activity [MoA]

MeSH Pharmacological Classification · 1 件

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)

応用分野 · 2 件

使用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) 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

一般的な説明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.