1-[(2,4-dichlorophenyl)methyl]-1H-indazole-3-carboxylic acid

• ChemBase ID: 70625
• Molecular Formular: C15H10Cl2N2O2
• Molecular Mass: 321.1581
• Monoisotopic Mass: 320.01193293
• SMILES: n1(nc(c2ccccc12)C(=O)O)Cc1c(cc(cc1)Cl)Cl
• Canonical SMILES: Clc1ccc(c(c1)Cl)Cn1nc(c2c1cccc2)C(=O)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2,4-dichlorophenyl)methyl]-1H-indazole-3-carboxylic acid
• IUPAC Traditional name: DICA
• Synonyms: 1-(2,4-Dichlorobenzyl)-1H-indazole-3-carboxylic acid; Lonidamine; 1-(2,4-Dichlorobenzyl)-1H-indazole-3-carboxylic acid; Diclondazolic acid; Lonidamine

Database IDs

• CAS Number: 50264-69-2
• EC Number: 256-510-0
• MDL Number: MFCD00866285
• PubChem SID: 24278515; 162036340
• PubChem CID: 39562

CALCULATED PROPERTIES

• Acid pKa: 3.1167057
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.040736
• LogD (pH = 7.4): 0.9369768
• Log P: 4.3959794
• Molar Refractivity: 92.3955 cm^3
• Polarizability: 32.088455 Å^3
• Polar Surface Area: 55.12 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C
• Storage Warning: IRRITANT
• RTECS: NK7886000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-22-40
• Safety Statements: 53-22-36/37/39-45
• TSCA Listed: false
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H351-H360
• GHS Precautionary statements: P201-P281-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Purity: 95+%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C15H10Cl2N2O2

DETAILS

Selleck Chemicals - S2610

Research Area: Cancer
Biological Activity:
Lonidamine is an orally administered small molecule hexokinase inactivator with an IC50 of 0.85 mM. Lonidamine inhibits glycolysis by the inactivation of hexokinase. Interestingly, Lonidamine seems to enhance aerobic glycolysis in normal cells, but suppress glycolysis in cancer cells. This is most likely through the inhibition of the mitochondrially bound hexokinase. Lonidamine inhibits both respiration and glycolysis leading to a decrease in cellular ATP. In addition, lonidamine may increase programmed cell death. This stems from the observation that mitochondria and mitochondria-bound hexokinase are crucial for induction of apoptosis. In vitro models with lonidamine exhibit the hallmarks of apoptosis, including mitochondrial membrane depolarization, release of cytochrome C, phosphatidylserine externalization, and DNA fragmentation. Lonidamine also blocks CFTR Cl- channels in vitro. [1][2][3][4]References on Lonidamine[1] http://en.wikipedia.org/wiki/Lonidamine, , [2] Mol Biochem Parasitol., 2008 Apr, 158(2):202-7[3] Cancer Chemother Pharmacol. , 1989, 25(1):32-6[4] Rev Urol. , 2005, 7 Suppl 7:S21-6

Sigma Aldrich - L4900

Biochem/physiol Actions
Inhibits the energy metabolism of neoplastic cells by interfering with hexokinase and disrupting uncoupler-stimulated mitochondrial electron transport;1 damages cell and mitochondrial membranes.