Lonidamin

Lonidamine

HCID 39562CAS 50264-69-2

Grundinformationen

Standard-SMILES
O=C(O)c1nn(Cc2ccc(Cl)cc2Cl)c2ccccc12
InChIKey
WDRYRZXSPDWGEB-UHFFFAOYSA-N
Summenformel
C15H10Cl2N2O2
Durchschnittliche Molmasse
321,2 g/mol
Monoisotopische Masse
320,01193292

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Lonidamine
IUPAC
1-[(2,4-dichlorophenyl)methyl]indazole-3-carboxylic acid
Lokaler Name
Lonidamin
Englischer Name
Lonidamine
Summenformel
C15H10Cl2N2O2
Molmasse
321.16

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,3
Polarare Oberfläche (TPSA)
55,1 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
3
Schwere Atome
21

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

Physikochemische Eigenschaften

Schmelzpunkt
207 · 207-209°C
Siedepunkt
537.9 · 537.9±45.0 °C(Predicted)
Dichte
1.4835 · 1.4835 (rough estimate)
Brechungsindex
1.607 · 1.6070 (estimate)
storage temp.
2 · Sealed in dry,2-8°C
Löslichkeit
Soluble in DMSO (up to 25 mg/ml).

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheitsdaten

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

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Mechanism of Action · 1 Eintrag

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 Einträge

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.

Anwendungen

BeschreibungLonidamine 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.

Verwendencontraceptive, spermicidal

Anbieter50 Anbieter

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]

Ergänzende Hinweise

DefinitionChEBI: 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.

Zugehörige Reaktionen

3

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