ARQ-501 (beta lapachone)

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

MedKoo CAT#: 200284

CAS#: 4707-32-8

Description: 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.


Price and Availability

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10mg
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100mg
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1g
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25mg
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200mg
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2g
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50mg
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500mg
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5g
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ARQ-501, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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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


Synonym: ARQ501 beta lapachone; 34Dihydro22dimethyl2Hnaphtho(12b)pyran56dione.

IUPAC/Chemical Name: 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

InChi Key: QZPQTZZNNJUOLS-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: O=C1C(CCC(C)(C)O2)=C2C3=CC=CC=C3C1=O


Technical Data

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, 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).

Harmonized System Code:
293490


Additional Information

 
 


References

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 MÃ