Lonidamine

Lonidamine is an orally administered small molecule hexokinase inactivator.Target: OthersLonidamine is a derivative of indazole-3-carboxylic acid, which for a long time, has been known to inhibit aerobic glycolysis in cancer cells. It 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. Later studies in Ehrlich ascites tumor cells showed that lonidamine inhibits bo

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, an antineoplastic agent, a geroprotector and an EC 2.7.1.1 (hexokinase) inhibitor. It is a member of indazoles, a dichlorobenzene and a monocarboxylic acid.|Lonidamine (LND) is a drug that interferes with energy metabolism of cancer cells, principally inhibiting aerobic glycolytic activity, by its effect on mitochondrially-bound hexokinase (HK). In such way LND could impair energy-requiring processes, as recovery from potentially lethal damage, induced by radiation treatment and by some cytotoxic drugs.|Lonidamine is an indazole carboxylic acid derivative that exhibits radiosensitizing and antiparasitic effects and interferes with the multidrug resistance mechanism.

Indoloquinone is added to an aqueous solution of sodium hydroxide to hydrolyze the ring to obtain compound (I). The compound (I) was mixed with an aqueous solution of sodium nitrite at 0°C, and the mixed solution was dropped into an aqueous solution of sulfuric acid, kept at 4°C or less, and continued to be stirred to obtain a diazonium salt solution. At 0°C with stirring, a concentrated solution of stannous chloride in hydrochloric acid was added dropwise, and stirring was continued. After filtration, a yellow-brown solid was obtained, and glacial acetic acid was recrystallized to obtain yellow needle-like crystals of indazole-3-carboxylic acid (III) in a yield of 51.2%. The indazole carboxylic acid, sodium hydroxide, water and potassium iodide are added together, under the protection of nitrogen, at 100° C. with stirring, 2, 4-dichlorobenzyl chloride is slowly added dropwise, and the reaction is continued after the addition. The crystals were collected by filtration and recrystallized with ethanol to obtain lonidamine, with a yield of 87.5% and a melting point of 205-206°C. The final reaction can also be carried out as follows: 1H-indino-3-carboxylic acid is dissolved in a solution of 8g sodium hydroxide and 160ml of water, and 2, 4-dichlorobenzyl chloride is added under heating and stirring in a water bath. Continue to heat for 3h, cool, and adjust to acidity with dilute hydrochloric acid. The precipitated crude clonidine is recrystallized with acetic acid, yield. 70%, melting point 207℃.

contraceptive, spermicidal

Molecular Weight:321.2
XLogP3:4.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:320.0119330
Monoisotopic Mass:320.0119330
Topological Polar Surface Area:55.1
Heavy Atom Count:21
Complexity:396
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes