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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 396
실험 및 물리화학적 성질
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).
- 산도 계수 (pKa)
- 3 · 3.00±0.10(Predicted)
- 물리적 상태
- 고체
- 색상
- 하얀색
- 안정성
- 1 · 제공된 대로 구매일로부터 1년 동안 안정적입니다. DMSO의 솔루션은 최대 1개월 동안 -20°에서 보관할 수 있습니다.
- 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
안전 및 규제
GHS 분류
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.
유해성 정보
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
- safety_code
- 53-22-36/37/39-45
- Hazard Classifications
- Acute Tox. 4 OralCarc. 2Repr. 1B
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
화학 및 산업
약리 정보
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.
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
상·하류 제품 정보
상류 원료
공급사50 곳
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
연결된 노트
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