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Merck

L4900

Lonidamine

≥98% (TLC), hexokinase inhibitor, powder

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill) :
C15H10Cl2N2O2
Numéro CAS:
50264-69-2
Poids moléculaire :
321.16
NACRES:
NA.77
PubChem Substance ID:
24278515
UNSPSC Code:
12352202
EC Number:
256-510-0
MDL number:
MFCD00866285

Nom du produit

Lonidamine, mitochondrial hexokinase inhibitor

InChI key

WDRYRZXSPDWGEB-UHFFFAOYSA-N

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)

SMILES string

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

assay

≥98% (TLC)

form

powder

solubility

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

Quality Level

200

Catégories apparentées

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

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

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

Classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number
0000375988
0000332130
0000239443
0000239443
0000332130

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Consulter la Bibliothèque de documents

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
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
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
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
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
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