|
| Product Name: | Lonidamine | | Synonyms: | af1890;lonidamin;1-[(2,4-dichlorophenyl)methyl]indazole-3-carboxylic acid;1H-Indazole-3-carboxylicacid, 1-[(2,4-dichlorophenyl)Methyl]-;1-(2,4-dichlorbenzyl)-indazole-3-carboxylicacid;1-(2,4-dichlorobenzyl)-1h-indazole-3-carboxylicaci;Lonidamine (AF1890);Lonidamine, 99%, mitochondrial hexokinase inhibitor | | CAS: | 50264-69-2 | | MF: | C15H10Cl2N2O2 | | MW: | 321.16 | | EINECS: | 256-510-0 | | Product Categories: | API;DORIDAMINA;inhibitor;Anti-cancer&immunity | | Mol File: | 50264-69-2.mol |  |
| | 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) |
| 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) |
| | 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 Preparation Products And Raw materials |
|
