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L4900

Lonidamine

Name: Lonidamine
Brand: SIGMA

mitochondrial hexokinase inhibitor

Synonym(s):

1-(2,4-Dichlorobenzyl)-1H-indazole-3-carboxylic acid, Diclondazolic acid

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₀Cl₂N₂O₂

CAS Number:

50264-69-2

Molecular Weight:

321.16

EC Number:

256-510-0

MDL number:

MFCD00866285

UNSPSC Code:

12352202

PubChem Substance ID:

24278515

NACRES:

NA.77

Quality Level

200

Assay

≥98% (TLC)

form

powder

solubility

chloroform: methanol (1:1): 9.80-10.20 mg/mL, clear, colorless to light yellow

SMILES string

OC(=O)c1nn(Cc2ccc(Cl)cc2Cl)c3ccccc13

InChI

1S/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)

InChI key

WDRYRZXSPDWGEB-UHFFFAOYSA-N

Application

Lonidamine has been used:

as an inhibitor of glycolysis to study its effects on the epithelial-mesenchymal transition (EMT) mechanism in cancer stem cells (CSC)
as mitochondrial permeability transition (MPT)- inducing drug to study its effects on temozolomide-resistant glioblastoma cell line
as mitochondrial hexokinase inhibitor to measure reactive oxygen species (ROS) in human acute myeloid leukemia cells

Biochem/physiol Actions

Lonidamine (LND) is an indazole derivative and is an anti-spermatogenic agent. It exhibits anti-tumor activity by sensitizing tumors to photodynamic, chemo-, radiotherapy, and hyperthermia. LND also interferes with energy metabolism by blocking glycolysis, adenosine diphosphate (ADP-), and uncoupler-stimulated respiration on various nicotinamide adenine dinucleotide (NAD-) and flavin adenine dinucleotide (FAD)-linked substrates, hexokinase activity, and oxygen uptake in Ehrlich ascites tumor cells. It blocks lactate export and pyruvate uptake into the mitochondria by inhibiting proton-linked monocarboxylate transporter (MCT) and mitochondrial pyruvate carrier (MPC), respectively.

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

Pictograms

GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H351,H360

Precautionary Statements

P201 - P301 + P312 + P330 - P308 + P313

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Repr. 1B

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Pharmacokinetics and biodistribution of lonidamine/paclitaxel loaded, EGFR-targeted nanoparticles in an orthotopic animal model of multi-drug resistant breast cancer.

Lara Milane et al.

Nanomedicine : nanotechnology, biology, and medicine, 7(4), 435-444 (2011-01-12)

The aim of this study was to assess the biodistribution and pharmacokinetics of epidermal growth factor receptor (EGFR)-targeted polymer-blend nanoparticles loaded with the anticancer drugs lonidamine and paclitaxel. Plasma, tumor, and tissue distribution profiles were quantified in an orthotopic animal

Increased apoptotic efficacy of lonidamine plus arsenic trioxide combination in human leukemia cells. Reactive oxygen species generation and defensive protein kinase (MEK/ERK, Akt/mTOR) modulation.

Eva Calviño et al.

Biochemical pharmacology, 82(11), 1619-1629 (2011-09-06)

Lonidamine is a safe, clinically useful anti-tumor drug, but its efficacy is generally low when used in monotherapy. We here demonstrate that lonidamine efficaciously cooperates with the anti-leukemic agent arsenic trioxide (ATO, Trisenox) to induce apoptosis in HL-60 and other

Chemosensitization by knockdown of adenine nucleotide translocase-2.

Morgane Le Bras et al.

Cancer research, 66(18), 9143-9152 (2006-09-20)

Mitochondrial membrane permeabilization (MMP) is a rate-limiting step of apoptosis, including in anticancer chemotherapy. Adenine nucleotide translocase (ANT) mediates the exchange of ADP and ATP on the inner mitochondrial membrane in healthy cells. In addition, ANT can cooperate with Bax

Curcumin stimulates reactive oxygen species production and potentiates apoptosis induction by the antitumor drugs arsenic trioxide and lonidamine in human myeloid leukemia cell lines.

Yolanda Sánchez et al.

The Journal of pharmacology and experimental therapeutics, 335(1), 114-123 (2010-07-08)

Arsenic trioxide (ATO, Trisenox) is an important antileukemic drug, but its efficacy is frequently low when used as a single agent. Here, we demonstrate that the apoptotic action of ATO is greatly increased when combined with subcytotoxic curcumin concentrations in

Discovery of Orexant and Anorexant Agents with Indazole Scaffold Endowed with Peripheral Antiedema Activity.

Marilisa P Dimmito et al.

Biomolecules, 9(9) (2019-09-19)

The endocannabinoid system represents an integrated neuronal network involved in the control of several organisms' functions, such as feeding behavior. A series of hybrids of 5-(4-chlorophenyl)-1-(2,4-dichloro-phenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide (mimonabant), a well-known inverse agonist of the type-1 cannabinoid receptor (CB1), once used as

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