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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 396
Experimentelle und physikochemische Eigenschaften
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).
- pka
- 3 · 3.00±0.10(Predicted)
- Aggregatzustand
- solid
- Farbe
- White
- Stabilität
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
- 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 Datenbank
- 50264 · 50264-69-2(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
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
- safety_code
- 53-22-36/37/39-45
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 4 OralCarc. 2Repr. 1B
Chemie und Industrie
Pharmakologische Informationen
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.
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
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
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
Verknüpfte Notizen
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