氯尼达明

Lonidamine

HCID 39562CAS 50264-69-2

基本信息

标准SMILES
O=C(O)c1nn(Cc2ccc(Cl)cc2Cl)c2ccccc12
InChIKey
WDRYRZXSPDWGEB-UHFFFAOYSA-N
分子式
C15H10Cl2N2O2
平均分子量
321.2 g/mol
单同位素质量
320.01193292

概述

Lonidamine is a member of the class of indazoles that is 1H-indazole that is substituted at positions 1 and 3 by 2,4-dichlorobenzyl and carboxy groups, respectively. It has a role as an antispermatogenic agent, a geroprotector, an antineoplastic agent and an EC 2.7.1.1 (hexokinase) inhibitor. It is a dichlorobenzene, a monocarboxylic acid and a member of indazoles.

名称与标识

首选名称
Lonidamine
IUPAC
1-[(2,4-dichlorophenyl)methyl]indazole-3-carboxylic acid
中文名
氯尼达明
英文名
Lonidamine
分子式
C15H10Cl2N2O2
分子量
321.16

名称与别名

lonidamine50264-69-21-(2,4-Dichlorobenzyl)-1H-indazole-3-carboxylic acidDiclondazolic acidDoridaminaLonidaminaLonidaminumAF 18901-[(2,4-dichlorophenyl)methyl]indazole-3-carboxylic acid1-(2,4-Dichlorbenzyl)-indazole-3-carboxylic acidDTXSID50207821-(2,4-dichlorobenzyl)indazole-3-carboxylic acid
展开更多名称
乐尼安洛尼达酸诺尼达明氯尼达明氯尼达明,99%HPLCLonidamine试剂Lonidamine试剂氯尼达明 B136654不存在氯尼达明, 线粒体己糖激酶抑制剂氯尼达明,10 MM DMSO 溶液dicalonidaminaf1890LonidnmineLONIDAMINGAF-1890:DICALonidamine, >=99%
NSC-741419NSC-758419U78804BIDR1H-Indazole-3-carboxylic acid, 1-((2,4-dichlorophenyl)methyl)-DTXCID90782CHEBI:501381H-Indazole-3-carboxylic acid, 1-[(2,4-dichlorophenyl)methyl]-1-((2,4-dichlorophenyl)methyl)indazole-3-carboxylic acid

数据库标识

CAS
50264-69-2
PubChem CID
39562
DTXSID
DTXSID5020782
ChEMBL
CHEMBL1257030
ChEBI
CHEBI:50138
UNII
U78804BIDR
EC Number
256-510-0
Nikkaji
J10.376D

性质

结构计算性质

XLogP
4.3
极性表面积
55.1 Ų
氢键供体
1
氢键受体
3
可旋转键
3
重原子
21

实验与物化性质

DrugsPharmaceuticals -> Listed in ZINC15

物理化学性质

熔点
207 · 207-209°C
沸点
537.9 · 537.9±45.0 °C(Predicted)
密度
1.4835 · 1.4835 (rough estimate)
折射率
1.607 · 1.6070 (estimate)
储存条件
2 · Sealed in dry,2-8°C
溶解度
Soluble in DMSO (up to 25 mg/ml).

化学性质

从乙醇结晶,熔点207℃。溶于甲醇或乙酸。急性毒性LD50小鼠,大鼠(mg/kg):900,1700口服;435,525腹腔注射。

安全与法规

GHS分类

GHS Classification · 4 条

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危害信息

Hazard Classes and CategoriesAcute Tox. 4 (100%)

安全数据

wgk
3
毒性
LD50 in mice, rats (mg/kg): 900, 1700 orally; 435, 525 i.p. (Heywood)
RTECS号
NK7886000
存储类别
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
安全说明
53-22-36/37/39-45
海关编码
29339900

化学与工业

药理信息

ATC Code · 2 条

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Mechanism of Action · 1 条

Lonidamine is an orally administered small molecule that inhibits glycolysis by the inactivation of hexokinase. Hexokinase is an enzyme that catalyzes glucose, the first step in glycolysis. The inhibition of hexokinase by lonidamine is well established. In addition, there is evidence that lonidamine may increase programmed cell death. This stems from the observation that mitochondria and mitochondria-bound hexokinase are crucial for induction of apoptosis; agents that directly effect mitochondria may, therefore, trigger apoptosis. Indeed, in vitro models with lonidamine exhibit the hallmarks of apoptosis, including mitochondrial membrane depolarization, release of cytochrome C, phosphatidylserine externalization, and DNA fragmentation. [PMID: 16986057]

Metabolism/MetabolitesLonidamine has known human metabolites that include (2S,3S,4S,5R)-6-[1-[(2,4-Dichlorophenyl)methyl]indazole-3-carbonyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.
MeSH Pharmacological Classification · 4 条

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Agents, either mechanical or chemical, which destroy spermatozoa in the male genitalia and block spermatogenesis.

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.

Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA.

应用领域

用途窄谱抗肿瘤药。可用于各种肿瘤,如乳腺癌、前列腺癌、肺癌及脑瘤等。另外也是一种杀精子药。

用途广谱抗肿瘤药,可用于各种肿瘤如乳腺癌、前列腺癌、肺癌及脑瘤等的治疗

制备方法 · 1 条

生产方法吲哚醌加入氢氧化钠的水溶液中,水解开环得到化合物(I)。将化合物(I)在0℃和亚硝酸钠水溶液混合,再将该混合液滴入硫酸水溶液中,保持在4℃以下,滴完继续搅拌得重氮盐溶液。于0℃和搅拌下,滴入氯化亚锡的浓盐酸溶液,继续搅拌。过滤得黄棕色固体,冰醋酸重结晶得黄色针状的吲唑-3-羧酸(Ⅲ)的结晶,收率51.2%。将该吲唑羧酸、氢氧化钠、水和碘化钾一起,在氮气保护下,在100℃和搅拌下,缓慢滴加2,4-二氯苄基氯,加毕继续反应。滤集晶体,用乙醇重结晶,得氯尼达明,收率87.5%,熔点205~206℃。其最后一步反应也可如下进行:1H-吲脞-3-羧酸溶于8g氢氧化钠和160ml水的溶液中,在水浴加热及搅拌下加入2,4-二氯苄基氯,加毕继续加热3h,冷却,用稀盐酸调至酸性,沉淀出的粗氯尼达明用醋酸重结晶,收率。70%,熔点207℃。

试剂价格

HY-B0486R · 5 mg
氯尼达明Lonidamine (Standard) — 1050元
HY-B0486R · 10 mg
氯尼达明Lonidamine (Standard) — 1680元

供应商50 家

郑州阿尔法化工有限公司+86-18530059196 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]

相关反应

3 条

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