. . ARQ-501 | beta lapachone | CAS#4707-32-8 | MedKoo Biosciences

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MedKoo product information:


ARQ-501 (beta lapachone)


Description of ARQ-501: ARQ-501 is a naphthoquinone compound derived from bark of Tabebuia sp., with antitumor, antibacterial, antifungal and antitrypanosomal activities. Beta-lapachone exerts its anti-tumor effect by indirect actions of inducing p53-independent apoptosis and cell cycle arrest mediated through altered activities of cell cycle control regulatory proteins; including down-regulating retinoblastoma protein (pRB), a transcriptional repressor target at transcription factor E2F-1, as well as induces expression of cyclin dependent kinase inhibitor 1A (CDKN1A or p21). Both E2F-1 and p21 are required for G1/S-phase transition during cell cycle. This agent also inhibits DNA topoisomerase I by a mechanism distinct from that of camptothecin, and thereby blocks the formation of a cleavable complex leading to enzyme inhibition and prevent DNA repair. Furthermore, beta-lapachone could induce reactive oxygen species in vivo, and result in cytotoxicity. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus). (last updated: 2/11/2015)


Current developer:  ArQule, Inc.


MedKoo Cat#: 200284

Name: ARQ-501 (beta lapachone)

CAS#: 4707-32-8

Synonym: ARQ-501, beta lapachone; 3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione.

IUPAC/Chemical name:


Chemical structure

Theoretical analysis

MedKoo Cat#: 200284
Name: ARQ-501 (beta lapachone)
CAS#:  4707-32-8  

Chemical Formula: C15H14O3

Exact Mass: 242.09429

Molecular Weight: 242.27

Elemental Analysis: C, 74.36; H, 5.82; O, 19.81


Availability and price:

ARQ-501, purity > 98%, is available through custom synthesis. Minimum 1 gram order is requested. Current shipping out time is about 70 days after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee:  $30.00 (USA); from $45.00 (Canada); from $70.00 (international).

10mg / not available

25mg / not available

50mg / not available

100mg / not available

200mg / not available

500mg / not available

1.0g / Ask price

2.0g / Ask price

5.0g / Ask price

Please ask price and availability of other quantity.



Technical data


Solid powder


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

Certificate of Analysis:

View CoA: current batch, Lot# (will be available for download when it's in stock)

QC data:

View QC data: current batch, Lot#  (will be available for download when it's in stock)

Safety Data Sheet (MSDS):

View Material Safety Data Sheet (MSDS)  (will be available for download when it's in stock)

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).


Soluble in DMSO, not in water

Shelf life:

>2 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).

Note: The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.


Protocols from literature

In vitro protocol::


In vivo protocol:


Clinical study:


Review papers:




Information about this agent



1: Kim JH, Lee SM, Myung CH, Lee KR, Hyun SM, Lee JE, Park YS, Jeon SR, Park JI, Chang SE, Hwang JS. Melanogenesis inhibition of β-lapachone, a natural product from Tabebuia avellanedae, with effective in vivo lightening potency. Arch Dermatol Res. 2015 Feb 8. [Epub ahead of print] PubMed PMID: 25663088.

2: Moore Z, Chakrabarti G, Luo X, Ali A, Hu Z, Fattah FJ, Vemireddy R, DeBerardinis RJ, Brekken RA, Boothman DA. NAMPT inhibition sensitizes pancreatic adenocarcinoma cells to tumor-selective, PAR-independent metabolic catastrophe and cell death induced by β-lapachone. Cell Death Dis. 2015 Jan 15;6:e1599. doi: 10.1038/cddis.2014.564. PubMed PMID: 25590809.

3: Menacho-Márquez M, Rodríguez-Hernández CJ, Villaronga MÁ, Pérez-Valle J, Gadea J, Belandia B, Murguía JR. eIF2 kinases mediate β-lapachone toxicity in yeast and human cancer cells. Cell Cycle. 2015 Jan 15:0. [Epub ahead of print] PubMed PMID: 25590579.

4: Ma X, Huang X, Moore Z, Huang G, Kilgore JA, Wang Y, Hammer S, Williams NS, Boothman DA, Gao J. Esterase-activatable β-lapachone prodrug micelles for NQO1-targeted lung cancer therapy. J Control Release. 2015 Feb 28;200:201-11. doi: 10.1016/j.jconrel.2014.12.027. Epub 2014 Dec 24. PubMed PMID: 25542645.

5: Jeong MH, Kim JH, Seo KS, Kwak TH, Park WJ. β-Lapachone attenuates mitochondrial dysfunction in MELAS cybrid cells. Biochem Biophys Res Commun. 2014 Oct 24;454(3):417-422. doi: 10.1016/j.bbrc.2014.10.093. [Epub ahead of print] PubMed PMID: 25451262.

6: Li JZ, Ke Y, Misra HP, Trush MA, Li YR, Zhu H, Jia Z. Mechanistic studies of cancer cell mitochondria- and NQO1-mediated redox activation of beta-lapachone, a potentially novel anticancer agent. Toxicol Appl Pharmacol. 2014 Dec 15;281(3):285-93. doi: 10.1016/j.taap.2014.10.012. Epub 2014 Oct 29. PubMed PMID: 25448047.

7: Ramos-Pérez C, Lorenzo-Castrillejo I, Quevedo O, García-Luis J, Matos-Perdomo E, Medina-Coello C, Estévez-Braun A, Machín F. Yeast cytotoxic sensitivity to the antitumour agent β-lapachone depends mainly on oxidative stress and is largely independent of microtubule- or topoisomerase-mediated DNA damage. Biochem Pharmacol. 2014 Nov 15;92(2):206-19. doi: 10.1016/j.bcp.2014.09.006. Epub 2014 Sep 21. PubMed PMID: 25241291.

8: Netto-Ferreira JC, Lhiaubet-Vallet V, Bernardes B, Ferreira AB, Miranda MÁ. Photophysics and photochemistry of the β-lapachone derived diphenyldihydrodioxin: generation and characterization of its cation radical. Photochem Photobiol Sci. 2014 Dec;13(12):1655-60. doi: 10.1039/c4pp00231h. Epub 2014 Sep 5. PubMed PMID: 25190482.

9: Yu HY, Kim SO, Jin CY, Kim GY, Kim WJ, Yoo YH, Choi YH. β-lapachone-Induced Apoptosis of Human Gastric Carcinoma AGS Cells Is Caspase-Dependent and Regulated by the PI3K/Akt Pathway. Biomol Ther (Seoul). 2014 May;22(3):184-92. doi: 10.4062/biomolther.2014.026. PubMed PMID: 25009698; PubMed Central PMCID: PMC4060078.

10: Park EJ, Min KJ, Lee TJ, Yoo YH, Kim YS, Kwon TK. β-Lapachone induces programmed necrosis through the RIP1-PARP-AIF-dependent pathway in human hepatocellular carcinoma SK-Hep1 cells. Cell Death Dis. 2014 May 15;5:e1230. doi: 10.1038/cddis.2014.202. PubMed PMID: 24832602; PubMed Central PMCID: PMC4047891.

11: Aires Ade L, Ximenes EC, Silva RA, Barbosa VX, Góes AJ, Peixoto CA, Souza VM, Albuquerque MC. Ultrastructural analysis of β-lapachone-induced surface membrane damage in male adult Schistosoma mansoni BH strain worms. Exp Parasitol. 2014 Jul;142:83-90. doi: 10.1016/j.exppara.2014.04.010. Epub 2014 Apr 24. PubMed PMID: 24768955.

12: Byun SJ, Son Y, Pae HO. Cytoprotective effect of β-lapachone by inducing heme oxygenase-1 expression and AMP-activated protein kinase activation in human endothelial cells. Eur Rev Med Pharmacol Sci. 2014;18(7):949-58. PubMed PMID: 24763872.

13: Jeong MH, Tran NK, Kwak TH, Park BK, Lee CS, Park TS, Lee YH, Park WJ, Yang DK. β-Lapachone ameliorates lipotoxic cardiomyopathy in acyl CoA synthase transgenic mice. PLoS One. 2014 Mar 10;9(3):e91039. doi: 10.1371/journal.pone.0091039. eCollection 2014. PubMed PMID: 24614171; PubMed Central PMCID: PMC3948739.

14: Lu CY. β-Lapachone ameliorates murine cisplatin nephrotoxicity: NAD⁺, NQO1, and SIRT1 at the crossroads of metabolism, injury, and inflammation. Kidney Int. 2014 Mar;85(3):496-8. doi: 10.1038/ki.2013.419. PubMed PMID: 24583980; PubMed Central PMCID: PMC3942788.

15: Park SW, Kim JH, Kim KE, Jeong MH, Park H, Park B, Suh YG, Park WJ, Kim JH. Beta-lapachone inhibits pathological retinal neovascularization in oxygen-induced retinopathy via regulation of HIF-1α. J Cell Mol Med. 2014 May;18(5):875-84. doi: 10.1111/jcmm.12235. Epub 2014 Feb 18. PubMed PMID: 24533641; PubMed Central PMCID: PMC4119393.

16: Ma X, Huang X, Huang G, Li L, Wang Y, Luo X, Boothman DA, Gao J. Prodrug strategy to achieve lyophilizable, high drug loading micelle formulations through diester derivatives of β-Lapachone. Adv Healthc Mater. 2014 Aug;3(8):1210-6. doi: 10.1002/adhm.201300590. Epub 2014 Feb 14. PubMed PMID: 24532286; PubMed Central PMCID: PMC4133338.

17: Kung HN, Weng TY, Liu YL, Lu KS, Chau YP. Sulindac compounds facilitate the cytotoxicity of β-lapachone by up-regulation of NAD(P)H quinone oxidoreductase in human lung cancer cells. PLoS One. 2014 Feb 5;9(2):e88122. doi: 10.1371/journal.pone.0088122. eCollection 2014. PubMed PMID: 24505400; PubMed Central PMCID: PMC3914905.

18: Shin S, Park J, Li Y, Min KN, Kong G, Hur GM, Kim JM, Shong M, Jung MS, Park JK, Jeong KH, Park MG, Kwak TH, Brazil DP, Park J. β-Lapachone alleviates alcoholic fatty liver disease in rats. Cell Signal. 2014 Feb;26(2):295-305. doi: 10.1016/j.cellsig.2013.11.020. Epub 2013 Nov 22. PubMed PMID: 24269941.

19: Zabka A, Trzaskoma P, Maszewski J. Dissimilar effects of β-lapachone- and hydroxyurea-induced DNA replication stress in root meristem cells of Allium cepa. Plant Physiol Biochem. 2013 Dec;73:282-93. doi: 10.1016/j.plaphy.2013.10.001. Epub 2013 Oct 11. PubMed PMID: 24184448.

20: Aires Ade L, Ximenes EC, Barbosa VX, Góes AJ, Souza VM, Albuquerque MC. β-Lapachone: a naphthoquinone with promising antischistosomal properties in mice. Phytomedicine. 2014 Feb 15;21(3):261-7. doi: 10.1016/j.phymed.2013.08.012. Epub 2013 Sep 30. PubMed PMID: 24090700.




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