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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 .ALPHA.-LAPACHONE

SMILES

CC1(C)CCC2=C(O1)C(=O)C3=CC=CC=C3C2=O

InChI

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

HIDE SMILES / InChI

Description

The bioactive quinone Alpha-lapachone was originally isolated from the heartwood of trees of the Bignoniaceae family (Tabebuia sp). It can also be found in other families such as Verbenaceae, Proteaceae, Leguminosae, Sapotaceae, Scrophulariaceae, and Malvaceae. Alpha-Lapachone showed potent cytotoxicity against different cancer cell lines. Alpha-lapachone is an "irreversible" inhibitor of topoisomerase II. Alpha-lapachone demonstrated antibacterial activity against pathogenic organisms Staphylococcus aureus and Salmonella typhi and antifungal activity against Candida albicans and Trichophyton mentagrophytes.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
11.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
1 uM alpha-lapachone failed to inhibit Trypanosoma cruzi epimastigotes DNA synthesis or the parasite growth in vitro, which suggests that inhibition of DNA synthesis was essential for beta-lapachone action on cell division and growth.