A naphthoquinone with diverse biological activities
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Lapachol

Item No. 30190

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthalenedione
CAS Number
84-79-7
Synonyms
  • C.I. 75490
  • NSC 11905
  • NSC 629756
Molecular Formula
C15H14O3
Formula Weight
242.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10mg/mLDMSO: 10mg/mLEthanol: 1mg/mL
λmax
253, 282 nm
SMILES
O=C1C(C/C=C(C)/C)=C(O)C(C2=CC=CC=C21)=O
InChi Code
InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,18H,8H2,1-2H3
InChi Key
CIEYTVIYYGTCCI-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $40

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    250 mg

    $73

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    500 mg

    $132

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    1 g

    $246

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    Product Description

    Lapachol is a naphthoquinone originally isolated from T. impetiginosa and has diverse biological activities.1,2,3,4,5 It is larvicidal against T. canis when used at a concentration of 2 mg/ml.1 Lapachol (10 and 100 µM) inhibits topoisomerase I and topoisomerase II activities, as well as induces apoptosis and DNA damage in C6 rat glioma cells.2 It reduces B. atrox venom phospholipase A2 (PLA2) activity in a turbidimetric assay when used at a concentration of 10 µg/ml.3 Lapachol (3 and 10 mg/kg) reduces synovial leukocyte infiltration and joint destruction in a mouse model of collagen-induced arthritis.4 It also reduces carrageenan-induced paw edema and abscess formation in rats.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mata-Santos, T., Pinto, N.F., Mata-Santos, H.A., et al. Anthelmintic activity of lapachol, β-lapachone and its derivatives against Toxocara canis larvae. Rev. Inst. Med. Trop. Sao Paulo 57(3), 197-204 (2015).

    2. Xu, H., Chen, Q., Wang, H., et al. Inhibitory effects of lapachol on rat C6 glioma in vitro and in vivo by targeting DNA topoisomerase I and topoisomerase II. J. Exp. Clin. Cancer Res. 35(1), 178 (2016).

    3. Strauch, M.A., Tomaz, M.A., Monteiro-Machado, M., et al. Lapachol and synthetic derivatives: In vitro and in vivo activities against Bothrops snake venoms. PLoS One 14(1), (2019).

    4. Peres, R.S., Santos, G.B., Cecilio, N.T., et al. Lapachol, a compound targeting pyrimidine metabolism, ameliorates experimental autoimmune arthritis. Arthritis Res. Ther. 19(1), 47 (2017).

    5. de Almeida, E.R., da Silva Filho, A.A., do Santos, E.R., et al. Antiinflammatory action of lapachol. J. Ethnopharmacol. 29(2), 239-241 (1990).