Lonidamine

HCID 39562CAS 50264-69-2

기본 정보

표준 SMILES
O=C(O)c1nn(Cc2ccc(Cl)cc2Cl)c2ccccc12
InChIKey
WDRYRZXSPDWGEB-UHFFFAOYSA-N
분자식
C15H10Cl2N2O2
평균 분자량
321.2 g/mol
단동위원소 질량
320.01193292

개요

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.

이름 및 식별자

우선 이름
Lonidamine
IUPAC
1-[(2,4-dichlorophenyl)methyl]indazole-3-carboxylic acid
영어명
Lonidamine
분자식
C15H10Cl2N2O2
분자량
321.16

이름 및 동의어

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
이름 더 보기
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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
4.3
극성 표면적
55.1 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
3
무거운 원자 수
21

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15

물리화학적 성질

녹는점
207 · 207-209°C
끓는 점
537.9 · 537.9±45.0 °C(Predicted)
밀도
1.4835 · 1.4835 (rough estimate)
굴절률
1.607 · 1.6070 (estimate)
저장 조건
2 · Sealed in dry,2-8°C
용해도
DMSO에 용해됩니다(최대 25mg/ml).

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (100%)

안전 데이터

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

화학 및 산업

약리 정보

ATC Code · 2건

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Mechanism of Action · 1건

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 · 4건

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.

응용 분야

개요Lonidamine 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.

용도contraceptive, spermicidal

공급사50 곳

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]

추가 설명

정의ChEBI: 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.

관련 반응

3건

연결된 노트

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