Lapachol
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 598388

CAS#: 84-79-7

Description: Lapachol has antimicrobial properties against many pathogens. It has anti-inflammatory, analgesic and antibiotic properties. It is inhibitor of epithelial tumors in Drosophila melanogaster heterozygote.

Chemical Structure

img
Lapachol
CAS# 84-79-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 598388
Name: Lapachol
CAS#: 84-79-7
Chemical Formula: C15H14O3
Exact Mass: 242.09
Molecular Weight: 242.274
Elemental Analysis: C, 74.36; H, 5.82; O, 19.81

Price and Availability

Size Price Availability Quantity
250mg USD 285 2 Weeks
500mg USD 450 2 Weeks
1g USD 750 2 Weeks
Bulk inquiry

Synonym: Lapachol; NSC-11905; NSC 11905; NSC11905; Tecomin; Bethabarra wood;

IUPAC/Chemical Name: 2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione

InChi Key: CIEYTVIYYGTCCI-UHFFFAOYSA-N

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

SMILES Code: O=C1C(O)=C(C/C=C(C)\C)C(C2=C1C=CC=C2)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities.
In vitro activity: Moreover, lapachol decreased the expression level of p-p38 among MAPKs compared with the PMA treatment group. It was also found that the expression level of p65, a part of NF-kB, in nuclei was reduced in the presence of lapachol above 0.5 μM compared with the PMA treatment group. In addition, lapachol inhibited the invasion of human fibrosarcoma cells stimulated with VEGF. Reference: Curr Mol Pharmacol. 2021 Oct 25;14(4):620-626. https://pubmed.ncbi.nlm.nih.gov/33019942/
In vivo activity: In vivo, LAP (lapachol) treatment markedly reduced CIA (collagen-induced arthritis) and AIA (antigen-induced arthritis) progression as evidenced by the reduction in clinical score, articular tissue damage, and inflammation. These findings propose a binding model of interaction and support the ability of LAP to inhibit DHODH, decreasing lymphocyte proliferation and attenuating the severity of experimental autoimmune arthritis. Therefore, LAP could be considered as a potential immunosuppressive lead candidate with potential therapeutic implications for RA (rheumatoid arthritis). Reference: Arthritis Res Ther. 2017 Mar 7;19(1):47. https://pubmed.ncbi.nlm.nih.gov/28270195/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 74.0 305.44

Preparing Stock Solutions

The following data is based on the product molecular weight 242.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Kim J, Kim MM. Effect of Lapachol on the Inhibition of Matrix Metalloproteinase Related to the Invasion of Human Fibrosarcoma Cells. Curr Mol Pharmacol. 2021 Oct 25;14(4):620-626. doi: 10.2174/1874467213666201005122230. PMID: 33019942. 2. Linzner N, Fritsch VN, Busche T, Tung QN, Loi VV, Bernhardt J, Kalinowski J, Antelmann H. The plant-derived naphthoquinone lapachol causes an oxidative stress response in Staphylococcus aureus. Free Radic Biol Med. 2020 Oct;158:126-136. doi: 10.1016/j.freeradbiomed.2020.07.025. Epub 2020 Jul 24. PMID: 32712193. 3. Peres RS, Santos GB, Cecilio NT, Jabor VA, Niehues M, Torres BG, Buqui G, Silva CH, Costa TD, Lopes NP, Nonato MC, Ramalho FS, Louzada-Júnior P, Cunha TM, Cunha FQ, Emery FS, Alves-Filho JC. Lapachol, a compound targeting pyrimidine metabolism, ameliorates experimental autoimmune arthritis. Arthritis Res Ther. 2017 Mar 7;19(1):47. doi: 10.1186/s13075-017-1236-x. PMID: 28270195; PMCID: PMC5341405. 4. Xu H, Chen Q, Wang H, Xu P, Yuan R, Li X, Bai L, Xue M. 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. 2016 Nov 16;35(1):178. doi: 10.1186/s13046-016-0455-3. PMID: 27852319; PMCID: PMC5112657.
In vitro protocol: 1. Kim J, Kim MM. Effect of Lapachol on the Inhibition of Matrix Metalloproteinase Related to the Invasion of Human Fibrosarcoma Cells. Curr Mol Pharmacol. 2021 Oct 25;14(4):620-626. doi: 10.2174/1874467213666201005122230. PMID: 33019942. 2. Linzner N, Fritsch VN, Busche T, Tung QN, Loi VV, Bernhardt J, Kalinowski J, Antelmann H. The plant-derived naphthoquinone lapachol causes an oxidative stress response in Staphylococcus aureus. Free Radic Biol Med. 2020 Oct;158:126-136. doi: 10.1016/j.freeradbiomed.2020.07.025. Epub 2020 Jul 24. PMID: 32712193.
In vivo protocol: 1. Peres RS, Santos GB, Cecilio NT, Jabor VA, Niehues M, Torres BG, Buqui G, Silva CH, Costa TD, Lopes NP, Nonato MC, Ramalho FS, Louzada-Júnior P, Cunha TM, Cunha FQ, Emery FS, Alves-Filho JC. Lapachol, a compound targeting pyrimidine metabolism, ameliorates experimental autoimmune arthritis. Arthritis Res Ther. 2017 Mar 7;19(1):47. doi: 10.1186/s13075-017-1236-x. PMID: 28270195; PMCID: PMC5341405. 2. Xu H, Chen Q, Wang H, Xu P, Yuan R, Li X, Bai L, Xue M. 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. 2016 Nov 16;35(1):178. doi: 10.1186/s13046-016-0455-3. PMID: 27852319; PMCID: PMC5112657.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Oliveira Silva E, Cruz de Carvalho T, Parshikov IA, Alves dos Santos R, Silva Emery F, Jacometti Cardoso Furtado NA. Cytotoxicity of lapachol metabolites produced by probiotics. Lett Appl Microbiol. 2014 Jul;59(1):108-14. doi: 10.1111/lam.12251. Epub 2014 Apr 9. PubMed PMID: 24635204.

2: Xu H, Chen Q, Wang H, Xu P, Yuan R, Li X, Bai L, Xue M. 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. 2016 Nov 16;35(1):178. PubMed PMID: 27852319; PubMed Central PMCID: PMC5112657.

3: Mata-Santos T, Pinto NF, Mata-Santos HA, De Moura KG, Carneiro PF, Carvalho Tdos S, Del Rio KP, Pinto Mdo C, Martins LR, Fenalti JM, Da Silva PE, Scaini CJ. ANTHELMINTIC ACTIVITY OF LAPACHOL, β-LAPACHONE AND ITS DERIVATIVES AGAINST Toxocara canis LARVAE. Rev Inst Med Trop Sao Paulo. 2015 May-Jun;57(3):197-204. doi: 10.1590/S0036-46652015000300003. PubMed PMID: 26200958; PubMed Central PMCID: PMC4544242.

4: Bai L, Han Y, Yao J, Li X, Li Y, Xu P, Xue M. Structural elucidation of the metabolites of lapachol in rats by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jan 1;944:128-35. doi: 10.1016/j.jchromb.2013.11.024. Epub 2013 Nov 22. PubMed PMID: 24316523.

5: Barbosa MI, Corrêa RS, de Oliveira KM, Rodrigues C, Ellena J, Nascimento OR, Rocha VP, Nonato FR, Macedo TS, Barbosa-Filho JM, Soares MB, Batista AA. Antiparasitic activities of novel ruthenium/lapachol complexes. J Inorg Biochem. 2014 Jul;136:33-9. doi: 10.1016/j.jinorgbio.2014.03.009. Epub 2014 Mar 27. PubMed PMID: 24727183.

6: Silva EO, Ruano-González A, dos Santos RA, Sánchez-Maestre R, Furtado NA, Collado IG, Aleu J. Antifungal and Cytotoxic Assessment of Lapachol Derivatives Produced by Fungal Biotransformation. Nat Prod Commun. 2016 Jan;11(1):95-8. PubMed PMID: 26996030.

7: Souza MA, Johann S, Lima LA, Campos FF, Mendes IC, Beraldo H, Souza-Fagundes EM, Cisalpino PS, Rosa CA, Alves TM, de Sá NP, Zani CL. The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives. Mem Inst Oswaldo Cruz. 2013 May;108(3). pii: S0074-02762013000300342. doi: 10.1590/S0074-02762013000300013. PubMed PMID: 23778660; PubMed Central PMCID: PMC4005582.

8: Genovese S, Taddeo VA, Epifano F, Fiorito S. Complexes of Lapachol and Lawsone with Lanthanides. Nat Prod Commun. 2015 Nov;10(11):1811-2. PubMed PMID: 26749803.

9: Okumura N, Wakamatsu S, Uno B. Electrochemical analysis in a liposome suspension using lapachol as a hydrophobic electro active species. Chem Pharm Bull (Tokyo). 2014;62(1):88-91. PubMed PMID: 24390497.

10: Parrilha GL, Vieira RP, Campos PP, Silva GD, Duarte LP, Andrade SP, Beraldo H. Coordination of lapachol to bismuth(III) improves its anti-inflammatory and anti-angiogenic activities. Biometals. 2012 Feb;25(1):55-62. doi: 10.1007/s10534-011-9481-y. Epub 2011 Aug 6. PubMed PMID: 21822673.

11: Fiorito S, Epifano F, Bruyère C, Mathieu V, Kiss R, Genovese S. Growth inhibitory activity for cancer cell lines of lapachol and its natural and semi-synthetic derivatives. Bioorg Med Chem Lett. 2014 Jan 15;24(2):454-7. doi: 10.1016/j.bmcl.2013.12.049. Epub 2013 Dec 18. PubMed PMID: 24374273.

12: Eyong KO, Puppala M, Kumar PS, Lamshöft M, Folefoc GN, Spiteller M, Baskaran S. A mechanistic study on the Hooker oxidation: synthesis of novel indane carboxylic acid derivatives from lapachol. Org Biomol Chem. 2013 Jan 21;11(3):459-68. doi: 10.1039/c2ob26737c. Epub 2012 Nov 30. PubMed PMID: 23196897.

13: Aucélio RQ, Peréz-Cordovés AI, Xavier Lima JL, Ferreira AB, Esteva Guas AM, da Silva AR. Determination of lapachol in the presence of other naphthoquinones using 3MPA-CdTe quantum dots fluorescent probe. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Jan 1;100:155-60. doi: 10.1016/j.saa.2012.04.020. Epub 2012 Apr 28. PubMed PMID: 22591798.

14: Oliveira RA, Correia-Oliveira J, Tang LJ, Garcia RC. A proteomic insight into the effects of the immunomodulatory hydroxynaphthoquinone lapachol on activated macrophages. Int Immunopharmacol. 2012 Sep;14(1):54-65. doi: 10.1016/j.intimp.2012.05.022. Epub 2012 Jun 21. PubMed PMID: 22705049.

15: Zhang C, Qu Y, Niu B. Design, synthesis and biological evaluation of lapachol derivatives possessing indole scaffolds as topoisomerase I inhibitors. Bioorg Med Chem. 2016 Nov 15;24(22):5781-5786. doi: 10.1016/j.bmc.2016.09.034. Epub 2016 Sep 15. PubMed PMID: 27667553.

16: Matsui T, Ito C, Oda M, Itoigawa M, Yokoo K, Okada T, Furukawa H. Lapachol suppresses cell proliferation and secretion of interleukin-6 and plasminogen activator inhibitor-1 of fibroblasts derived from hypertrophic scars. J Pharm Pharmacol. 2011 Jul;63(7):960-6. doi: 10.1111/j.2042-7158.2011.01292.x. PubMed PMID: 21635262.

17: Oliveira RA, Azevedo-Ximenes E, Luzzati R, Garcia RC. The hydroxy-naphthoquinone lapachol arrests mycobacterial growth and immunomodulates host macrophages. Int Immunopharmacol. 2010 Nov;10(11):1463-73. doi: 10.1016/j.intimp.2010.08.023. Epub 2010 Sep 15. PubMed PMID: 20837170.

18: Kandioller W, Balsano E, Meier SM, Jungwirth U, Göschl S, Roller A, Jakupec MA, Berger W, Keppler BK, Hartinger CG. Organometallic anticancer complexes of lapachol: metal centre-dependent formation of reactive oxygen species and correlation with cytotoxicity. Chem Commun (Camb). 2013 Apr 25;49(32):3348-50. doi: 10.1039/c3cc40432c. PubMed PMID: 23505633.

19: Costa WF, Oliveira AB, Nepomuceno JC. Lapachol as an epithelial tumor inhibitor agent in Drosophila melanogaster heterozygote for tumor suppressor gene wts. Genet Mol Res. 2011 Dec 22;10(4):3236-45. doi: 10.4238/2011.December.22.1. PubMed PMID: 22194187.

20: Sunassee SN, Veale CG, Shunmoogam-Gounden N, Osoniyi O, Hendricks DT, Caira MR, de la Mare JA, Edkins AL, Pinto AV, da Silva Júnior EN, Davies-Coleman MT. Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells. Eur J Med Chem. 2013 Apr;62:98-110. doi: 10.1016/j.ejmech.2012.12.048. Epub 2013 Jan 5. PubMed PMID: 23353747.