Lonidamine

Base Information

• Chemical Name: Lonidamine
• CAS No.: 50264-69-2
• Deprecated CAS: 57571-43-4
• Molecular Formula: C15H10Cl2N2O2
• Molecular Weight: 321.163
• Hs Code.: 29339900
• European Community (EC) Number: 256-510-0
• NSC Number: 758419,741419
• UNII: U78804BIDR
• DSSTox Substance ID: DTXSID5020782
• Nikkaji Number: J10.376D
• Wikipedia: Lonidamine
• Wikidata: Q3836670
• NCI Thesaurus Code: C1146
• Metabolomics Workbench ID: 57340
• ChEMBL ID: CHEMBL1257030
• Mol file: 50264-69-2.mol

Synonyms:1-(2,4-dichlorobenzyl)indazole-3-carboxylic acid;AF 1890;diclondazolic acid;lonidamine

Chemical Property of Lonidamine

Chemical Property:

• Appearance/Colour: white to light yellow crystal
• Vapor Pressure: 2.11E-12mmHg at 25°C
• Melting Point: 207-209 °C
• Refractive Index: 1.678
• Boiling Point: 537.9 °C at 760 mmHg
• PKA: 3.00±0.10(Predicted)
• Flash Point: 280.6 °C
• PSA: 55.12000
• Density: 1.47 g/cm³
• LogP: 4.08960
• Storage Temp.: Store at RT
• Solubility.: Soluble in DMSO (up to 25 mg/ml).
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 320.0119330
• Heavy Atom Count: 21
• Complexity: 396

Purity/Quality:

99% ^*data from raw suppliers

Lonidamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 60-22-40
• Safety Statements: 53-22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=NN2CC3=C(C=C(C=C3)Cl)Cl)C(=O)O
• Recent ClinicalTrials: Study of the Efficacy and Safety of Lonidamine for the Treatment of Symptomatic Benign Prostatic Hyperplasia
• Recent EU Clinical Trials: A Randomised Phase 3, Double Blind, Placebo-Controlled Study of the Efficacy and Safety of Lonidamine for the Treatment of Symptomatic Benign Prostatic Hyperplasia
• 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). 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.
• Uses: contraceptive, spermicidal

Technology Process of Lonidamine

There total 14 articles about Lonidamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

methyl 1-(2,4-dichlorobenzyl)-1H-indazole-3-carboxylate (252025-50-6) → lonidamine (50264-69-2)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1002/cmdc.201700446

Reference yield: 84.0%

(1-(2,4-dichlorobenzyl)-1H-indazol-3-yl)methanol (920019-58-5) → lonidamine (50264-69-2)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone; at 20 ℃; for 24h;

DOI:10.1002/adsc.201500953

Reference yield: 60.0%

2,4-Dichlorobenzyl chloride (94-99-5) + methyl 1H-indazole-3-carboxylate (43120-28-1) → lonidamine (50264-69-2)

Guidance literature:

2,4-Dichlorobenzyl chloride; methyl 1H-indazole-3-carboxylate; With water; sodium hydroxide; at 100 ℃; for 4h;

With hydrogenchloride; In water; at 20 ℃; for 0.5h;

upstream raw materials:

methyl 1-(2,4-dichlorobenzyl)-1H-indazole-3-carboxylate

2,4-Dichlorobenzyl chloride

methyl 1H-indazole-3-carboxylate

2-bromophenyl methyl ketone

Downstream raw materials:

methyl 1-(2,4-dichlorobenzyl)-1H-indazole-3-carboxylate

Refernces

• 1、 -. "MODULATORS OF MAS-RELATED G-PROTEIN RECEPTOR X4 AND RELATED PRODUCTS AND METHODS". . . Retrieved 2022/04/03.
• 2、 Xie, Yongkang,Zhang, Shumiao,Ge, Xingxing,Ma, Wenli,He, Xiaolin,Zhao, Yao,Ye, Juan,Zhang, Hongmin,Wang, Anwei,Liu, Zhe. "Lysosomal-targeted anticancer half-sandwich iridium(III) complexes modified with lonidamine amide derivatives". . . Retrieved 2020/03/05.