Structure via PubChem · Public domain (PubChem)
lonidamine
Sign in to saveAlso known as DICA, 1-(2,4-dichlorbenzyl)-indazole-3-carboxylic acid, diclondazolic acid, Lonidamin, lonidamina, Doridamina, lonidaminum
Lonidamine 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 both respiration and glycolysis leading to a decrease in cellular ATP.
In the Vinony graph
Vinony's link graph records 601 inbound references to lonidamine, and connects out to tiazofurin, medication and digital object identifier.
It is catalogued under topics including Antineoplastic drugs, Chemical pages without DrugBank identifier and Drugboxes which contain changes to verified fields.
Vinony links it to 6 Wikipedia language editions.
Chemical data
- Formula
- C15H10Cl2N2O2
- Molecular weight
- 321.2 g/mol
- IUPAC name
- 1-[(2,4-dichlorophenyl)methyl]indazole-3-carboxylic acid
- SMILES
- C1=CC=C2C(=C1)C(=NN2CC3=C(C=C(C=C3)Cl)Cl)C(=O)O
- InChIKey
- WDRYRZXSPDWGEB-UHFFFAOYSA-N
- XLogP
- 4.3
- Polar surface area
- 55.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- neoplasm, benign prostatic hyperplasia
via ChEMBL · EBI
Research
576 papers- Lonidamine and related compounds.Progress in medicinal chemistry · 1984
- Lonidamine: an overview.Seminars in oncology · 1991
- Lonidamine, a new approach to cancer therapy.Oncology · 1984
- Reviving Lonidamine and 6-Diazo-5-oxo-L-norleucine to Be Used in Combination for Metabolic Cancer Therapy.BioMed research international · 2015
- Lonidamine: efficacy and safety in clinical trials for the treatment of solid tumors.Drugs of today (Barcelona, Spain : 1998) · 2003
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 320.012
- Has use
- medication
Show 3 more facts
- chemical formula
- C₁₅H₁₀Cl₂N₂O₂
- canonical SMILES
- C1=CC=C2C(=C1)C(=NN2CC3=C(C=C(C=C3)Cl)Cl)C(=O)O
- World Health Organisation international non-proprietary name
- lonidamine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Lonidamine 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 both respiration and glycolysis leading to a decrease in cellular ATP.
Clinical trials of lonidamine in combination with other anticancer agents for a variety of cancers has begun. This is due to its proven ability to inhibit energy metabolism in cancer cells, and to enhance the activity of anticancer agents.
Excerpted from Wikipedia’s “lonidamine” article, available under the CC BY-SA 4.0 licence.