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50264-69-2

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50264-69-2 Usage

Description

Different sources of media describe the Description of 50264-69-2 differently. You can refer to the following data:
1. 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).
2. 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.

References

Different sources of media describe the References of 50264-69-2 differently. You can refer to the following data:
1. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1477623/ https://en.wikipedia.org/wiki/Lonidamine
2. 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

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.

Check Digit Verification of cas no

The CAS Registry Mumber 50264-69-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,0,2,6 and 4 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 50264-69:
(7*5)+(6*0)+(5*2)+(4*6)+(3*4)+(2*6)+(1*9)=102
102 % 10 = 2
So 50264-69-2 is a valid CAS Registry Number.
InChI:InChI=1/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)

50264-69-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name lonidamine

1.2 Other means of identification

Product number -
Other names Lonidaminum

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:50264-69-2 SDS

50264-69-2Relevant articles and documents

Multiaction Platinum(IV) Prodrug Containing Thymidylate Synthase Inhibitor and Metabolic Modifier against Triple-Negative Breast Cancer

Ji, Liang-Nian,Mao, Zong-Wan,Muhammad, Nafees,Nasreen, Sadia,Nawaz, Uroosa,Tan, Cai-Ping,Wang, Fang-Xin,Wang, Jie

, p. 12632 - 12642 (2020)

Multifunctional platinumIV anticancer prodrugs have the potential to enrich the anticancer properties and overcome the clinical problems of drug resistance and side effects of platinumII anticancer agents. Herein, we develop dual and triple action platinumIV complexes with targeted and biological active functionalities. One complex (PFL) that consists of cisplatin, tegafur, and lonidamine exhibits strong cytotoxicity against triple negative breast cancer (TNBC) cells. Cellular uptake and distribution studies reveal that PFL mainly accumulates in mitochondria. As a result, PFL disrupts the mitochondrial ultrastructure and induces significant alterations in the mitochondrial membrane potential, which further leads to an increase in production of reactive oxygen species (ROS) and a decrease in ATP synthesis in MDA-MB-231 TNBCs. Western blot analysis reveals the formation of ternary complex of thymidylate synthase, which shows the intracellular conversion of tegafur into 5-FU after its release from PFL. Furthermore, treatment with PFL impairs the mitochondrial function, leading to the inhibition of glycolysis and mitochondrial respiration and induction of apoptosis through the mitochondrial pathway. The RNA-sequencing experiment shows that PFL can perturb the pathways involved in DNA synthesis, DNA damage, metabolism, and transcriptional activity. These findings demonstrate that PFL intervenes in several cellular processes including DNA damage, thymidylate synthase inhibition, and perturbation of the mitochondrial bioenergetics to kill the cancer cells. The results highlight the significance of a triple-action prodrug for efficient anticancer therapy for TNBCs.

Preparation methods of 1H-indazol-3-carboxylic acid derivative, granisetron and lonidamine

-

Paragraph 0122; 0133-0135, (2021/05/12)

The invention relates to preparation methods of a 1H-indazol-3-carboxylic acid derivative, granisetron and lonidamine. The 1H-indazol-3-carboxylic acid derivative is a compound with a structure shown in a formula (1) and a formula (2), and is mainly structurally characterized by having a 1H-indazol-3-carboxylic acid amide skeleton and a 1H-indazol-3-carboxylic ester skeleton. The 1H-indazol-3-carboxylic acid derivative can be synthesized by taking simple o-aminophenylacetic acid amide or o-aminophenylacetic acid ester as an initial raw material. The 1H-indazol-3-carboxylic acid derivative is a key intermediate for synthesizing a plurality of medicines, such as granisetron, lonidamine and the like. The synthesis method of the 1H-indazol-3-carboxylic acid derivative and the drug molecules glassetron and lonidamine is simple, the reaction condition is mild, the reaction speed is high, the yield is high, and purification is easy.

Sulfocoumarin-, Coumarin-, 4-Sulfamoylphenyl-Bearing Indazole-3-carboxamide Hybrids: Synthesis and Selective Inhibition of Tumor-Associated Carbonic Anhydrase Isozymes IX and XII

Angapelly, Srinivas,Sri Ramya,Angeli, Andrea,Supuran, Claudiu T.,Arifuddin, Mohammed

, p. 1578 - 1584 (2017/10/16)

A series of sulfocoumarin-, coumarin-, and 4-sulfamoylphenyl-bearing indazole-3-carboxamide hybrids were synthesized and investigated as inhibitors of the human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I and II (cytosolic isozymes), as well as hCA IX and XII (transmembrane, tumor-associated enzymes). Compounds 6 a–g (amide derivatives) and 7 a–h (triazoles) act as “prodrugs”, and their hydrolysis products are the de facto CA inhibitors. These compounds displayed sub-micromolar to high-nanomolar inhibitory activity against hCA isoforms IX and XII, which were recently validated as antitumor drug targets. Moreover, no inhibition of the off-target hCA I and II isoforms was observed. Compounds 8 a–f (another set of triazoles) exhibited nanomolar inhibition against hCA isoforms I, II, IX and XII, among which compounds 8 c, 8 d, and 8 f were found to inhibit the tumor-associated hypoxia-induced hCA isoform IX with Ki values of 1.8, 2.3, and 2.0 nm respectively. Further exploration of these compounds could be useful for the development of novel antitumor agents with selective mechanisms of CA inhibitory action.

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