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L4900

Lonidamine

≥98% (TLC), hexokinase inhibitor, powder

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
NACRES:
NA.77
PubChem Substance ID:
24278515
UNSPSC Code:
12352202
EC Number:
256-510-0
MDL number:
MFCD00866285
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Product Name

Lonidamine, mitochondrial hexokinase inhibitor

Quality Segment

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

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

Storage Class

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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