Lonidamine Chemical Properties

Melting point:

207-209°C

Boiling point:

537.9±45.0 °C(Predicted)

Density 

1.4835 (rough estimate)

refractive index 

1.6070 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

Soluble in DMSO (up to 25 mg/ml).

pka

3.00±0.10(Predicted)

form 

solid

color 

White

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.

InChIKey

WDRYRZXSPDWGEB-UHFFFAOYSA-N

CAS DataBase Reference

50264-69-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

60-22-40

Safety Statements 

53-22-36/37/39-45

WGK Germany 

3

RTECS 

NK7886000

HS Code 

29339900

Toxicity

LD50 in mice, rats (mg/kg): 900, 1700 orally; 435, 525 i.p. (Heywood)

MSDS

• Language:English Provider:1-(2,4-Dichlorobenzyl)-1H-indazole-3-carboxylic acid
• Language:English Provider:SigmaAldrich

Lonidamine Usage And Synthesis

Description

Lonidamine is a derivative of indazole-3-carboxylic acid. It is a kind of orally administrated small molecule, which can inhibit the glycolysis process through inactivating the hexokinase (the first step in glycolysis). It has been shown that cancer cell primarily generates energy through glycolysis process. Therefore, Lonidamine has been used for the treatment of several kinds of cancers. One special property of Lonidamine is that it seems to enhance aerobic glycolysis in normal cells, but inhibit glycolysis only in cancer cells. In addition, there are also evidences that Lonidamine may increase the occurrence of apoptosis. It has also been shown that Lonidamine is effective in the treatment of benigh prostatic hyperplasia (BPH).

References

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1477623/
https://en.wikipedia.org/wiki/Lonidamine

Description

Lonidamine 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.

Originator

Angelini (Italy)

Uses

contraceptive, spermicidal

Definition

ChEBI: 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.

brand name

Doridamina

Biological Activity

Anticancer and antispermatogenic agent in vitro and in vivo . Inhibits cellular energy metabolism in some cells via inhibition of mitochondrial hexokinase. Also blocks CFTR Cl - channels in vitro .

Biochem/physiol Actions

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

storage

Room temperature

References

1) Gatto?et al. (2002),?Recent studies on lonidamine, the lead compound of the antispermatogenic indazol-carboxylic acids; Contraception,?65?277 2) Floridi?et al., (1981),?Effect of Lonidamine on the Energy Metabolism of Ehrlich Ascites Tumor Cells; Cancer Res.,?41?4661 3) Ravagnan?et al. (1999),?Lonidamine triggers apoptosis via a direct, Bcl-2-inhibited effect on the mitochondrial permeability transition pore; Oncogene,?18?2537 4) Ben-Horin?et al. (1995),?Mechanism of Action of the Antineoplastic Drug Lonidamine: 31P and 13C Nuclear Magnetic Resonance Studies; Cancer Res.?55?2814 5) Nath?et al. (2016),?Mechanism of antineoplastic activity of lonidamine; Biochim.Biophys.Acta Reviews on Cancer?1866?151

Lonidamine(50264-69-2)Related Product Information

• Indazole-3-carboxylic acid
• Triphenylphosphine
• Dichloroethane
• Thionyl chloride
• Citric acid
• Folic acid
• Hyaluronic acid
• 2-Phenylphenol
• Quinclorac
• Sodium dichloroisocyanurate
• Ethyl 2-(Chlorosulfonyl)acetate
• Dichlorodiphenylsilane
• Voriconazole
• Ascoric Acid
• Phenylacetone
• 1-METHYL-1H-INDAZOLE-3-CARBALDEHYDE
• 3-METHYL-1H-INDAZOLE
• 1H-INDAZOLE-3-CARBALDEHYDE