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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 396
実験および物理化学的性質
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)。
- 酸解離定数(Pka)
- 3 · 3.00±0.10(Predicted)
- 外見
- 個体
- 色
- 白い
- 安定性
- -20 °C · -20°C の DMSO 溶液で最大 1 か月間保存できます。
- InChI
- InChI=1S/C15H10Cl2N2O2/c16-10-6-5-9(12(17)7-10)8-19-13-4-2-1-3-11(13)14(18-19)15(20)21/h1-7H,8H2,(H,20,21)
- InChIKey
- WDRYRZXSPDWGEB-UHFFFAOYSA-N
- SMILES
- N1(CC2=CC=C(Cl)C=C2Cl)C2=C(C=CC=C2)C(C(O)=O)=N1
- CAS データベース
- 50264 · 50264-69-2(CAS DataBase Reference)
安全と法規制
GHS分類
GHS Classification
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
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
- safety_code
- 53-22-36/37/39-45
- Hazard Classifications
- Acute Tox. 4 OralCarc. 2Repr. 1B
- 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
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Mechanism of Action
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]
MeSH Pharmacological Classification
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
上流・下流製品情報
上流原料
サプライヤー50 社
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
関連ノート
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