ロニダミン

Lonidamine

HCID 39562CAS 50264-69-2

基本情報

標準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
単同位体質量
320.01193292

概要

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.

名称と識別子

優先名称
Lonidamine
IUPAC
1-[(2,4-dichlorophenyl)methyl]indazole-3-carboxylic acid
現地名
ロニダミン
英語名
Lonidamine
分子式
C15H10Cl2N2O2
分子量
321.16

名称と別名

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
名称をさらに表示
1-(2,4-ジクロロベンジル)-1H-インダゾール-3-カルボン酸ドリダミナジクロンダゾール酸ロニダミン1-[(2,4-ジクロロフェニル)メチル]-1H-インダゾール-3-カルボン酸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

データベース識別子

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

物性

構造計算による物性

XLogP
4.3
極性表面積
55.1 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
3
重原子数
21

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

物理化学的性質

融点
207 · 207-209°C
沸点
537.9 · 537.9±45.0 °C(Predicted)
比重(密度)
1.4835 · 1.4835 (rough estimate)
屈折率
1.607 · 1.6070 (estimate)
貯蔵温度
2 · Sealed in dry,2-8°C
溶解性
DMSO に可溶 (最大 25 mg/ml)。

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

安全データ

wgk
3
rtecs
NK7886000
毒性
LD50 in mice, rats (mg/kg): 900, 1700 orally; 435, 525 i.p. (Heywood)
hs_code
29339900
risk_code
60-22-40
hazard_code
T

化学と産業

薬理情報

ATC Code · 2 件

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Mechanism of Action · 1 件

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 件

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.

応用分野

説明Lonidamine is an antineoplastic agent reportedly effective for the treatment of various cancers, including lung, breast, prostate and brain tumors. Its clinical effect appears to be associated with changes in cellular energy metabolism.

使用contraceptive, spermicidal

サプライヤー50 社

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]

補足説明

定義ChEBI: 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.

関連反応

3 件

関連ノート

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