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Details

Stereochemistry ACHIRAL
Molecular Formula C15H14O3
Molecular Weight 242.2699
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAPACHONE

SMILES

CC1(C)CCC2=C(O1)C3=CC=CC=C3C(=O)C2=O

InChI

InChIKey=QZPQTZZNNJUOLS-UHFFFAOYSA-N
InChI=1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3

HIDE SMILES / InChI

Description

Lapachone (aka beta-Lapachone) is an ortho naphthoquinone, originally isolated from a tree whose extract has been used medicinally for centuries. It has garnered interest as a potential therapeutic or lead compound against a number of disease conditions including cancers, and blindness due to retinopathy of prematurity. It is lethal to a number of cancer cell types at micromolar concentrations, and it is capable of enhancing the efficacy of radiation therapies against cultured cells. A number of clinical trials have been conducted.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
3.56 ng/mL
100 mg single, oral
LAPACHONE plasma
Homo sapiens
14.96 ng/mL
100 mg 2 times / day multiple, oral
LAPACHONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
22.71 ng × h/mL
100 mg single, oral
LAPACHONE plasma
Homo sapiens
93.69 ng × h/mL
100 mg 2 times / day multiple, oral
LAPACHONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.89 h
100 mg single, oral
LAPACHONE plasma
Homo sapiens
18.16 h
100 mg 2 times / day multiple, oral
LAPACHONE plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
In a phase I investigation of the safety and tolerability of beta-lapachone, healthy volunteers received either single doses of 300 mg or 400 mg; or multiple doses of 100 mg or 200 mg.
Route of Administration: Oral
In Vitro Use Guide
Human non-small cell lung cancer cell lines H1299 and NCI-H358 were grown in RPMI-1640 containing 10% heat-inactivated fetal bovine serum and 100U/mL each of penicillin and streptomycin. Cultures were incubated at 37 deg-C in a 5% CO2 atmosphere. Cells were seeded in 96-well plates and incubated for 24 hours then treated with 0, 1, 2, or 3 micro-M of beta-lapachone for another 24 and 48 hours. The percentage of viable cells was determined by using a CellTiter96 Aqueous One Cell Proliferation Assay Kit. Beta-lapachone decreased the viability of both H1299 and NCI-H358 in a dose- and time-dependent manner. The maximal decrease was observed at 48 h relative to the levels at 24 h. DAPI staining was carried out under a confocal microscope to investigate the morphological changes related to apoptosis. Beta-lapachone treated cells exhibited nuclear fragmentation at a concentration of 1, 2 and 3 micro-M after 48 hours.