Naproxcinod

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

MedKoo CAT#: 525730

CAS#: 163133-43-5

Description: Naproxcinod is a nitric oxide-releasing NSAID derivative. Naproxcinod significantly ameliorated skeletal muscle force and resistance to fatigue in sedentary as well as in exercised mice, reduced inflammatory infiltrates and fibrosis deposition in both cardiac and diaphragm muscles. Conversely, the equimolar dose of naproxen showed no effects on fibrosis and improved muscle function only in sedentary mice. In addition to anti-inflammatory activity, naproxcinod as a promising candidate for treatment of Duchenne Muscular Dystrophy.


Price and Availability

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Naproxcinod is not in stock, but 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#: 525730
Name: Naproxcinod
CAS#: 163133-43-5
Chemical Formula: C18H21NO6
Exact Mass: 347.13689
Molecular Weight: 347.367
Elemental Analysis: C, 62.24; H, 6.09; N, 4.03; O, 27.63


Synonym: Naproxen-N-butyl nitrate; Nitronaproxen; AZD 3582; AZD-3582; AZD3582; HCT3012; HCT-3012; HCT 3012; AR-P-900758XX; NO-naproxen; ZD-3582; ARP-900758XX; Naproxcinod

IUPAC/Chemical Name: 4-(nitrooxy)butyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate

InChi Key: AKFJWRDCWYYTIG-ZDUSSCGKSA-N

InChi Code: InChI=1S/C18H21NO6/c1-13(18(20)24-9-3-4-10-25-19(21)22)14-5-6-16-12-17(23-2)8-7-15(16)11-14/h5-8,11-13H,3-4,9-10H2,1-2H3/t13-/m0/s1

SMILES Code: C[C@@H](C1=CC=C2C=C(OC)C=CC2=C1)C(OCCCCO[N+]([O-])=O)=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


References

1: Miglietta D, De Palma C, Sciorati C, Vergani B, Pisa V, Villa A, Ongini E, Clementi E. Naproxcinod shows significant advantages over naproxen in the mdx model of Duchenne Muscular Dystrophy. Orphanet J Rare Dis. 2015 Aug 22;10:101. doi: 10.1186/s13023-015-0311-0. PubMed PMID: 26296873; PubMed Central PMCID: PMC4546261.
2: Li X, Zhang J, Bao Y, Ye Y, Li W, Yin W, Guo F, Chen A. WITHDRAWN: Efficacy and safety of short-term treatment of naproxcinod in patients with osteoarthritis (OA) of the hip: A prospective, randomized study. Arch Gerontol Geriatr. 2015 Jan 31. pii: S0167-4943(15)00013-8. doi: 10.1016/j.archger.2015.01.012. [Epub ahead of print] PubMed PMID: 25912890.
3: Shi X, Shang W, Wang S, Xue N, Hao Y, Wang Y, Sun M, Du Y, Cao D, Zhang K, Shi Q. Simultaneous quantification of naproxcinod and its active metabolite naproxen in rat plasma using LC-MS/MS: application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jan 26;978-979:157-62. doi: 10.1016/j.jchromb.2014.12.001. Epub 2014 Dec 11. PubMed PMID: 25550191.
4: Uaesoontrachoon K, Quinn JL, Tatem KS, Van Der Meulen JH, Yu Q, Phadke A, Miller BK, Gordish-Dressman H, Ongini E, Miglietta D, Nagaraju K. Long-term treatment with naproxcinod significantly improves skeletal and cardiac disease phenotype in the mdx mouse model of dystrophy. Hum Mol Genet. 2014 Jun 15;23(12):3239-49. doi: 10.1093/hmg/ddu033. Epub 2014 Jan 23. PubMed PMID: 24463621; PubMed Central PMCID: PMC4030778.
5: Inugala UR, Pothuraju NR, Vangala RR. Quality by design approach for the separation of naproxcinod and its related substances by fused core particle technology column. J Chromatogr Sci. 2013 May-Jun;51(5):453-9. doi: 10.1093/chromsci/bms162. Epub 2012 Oct 11. PubMed PMID: 23060406.
6: Naproxcinod. Prescrire Int. 2012 Jul;21(129):180. PubMed PMID: 22852285.
7: Townsend R, Bittar N, Rosen J, Smith W, Ramsay A, Chrysant SG, Weiss R, Pivodic A, Duquesroix B, Djian J. Blood pressure effects of naproxcinod in hypertensive patients. J Clin Hypertens (Greenwich). 2011 May;13(5):376-84. doi: 10.1111/j.1751-7176.2010.00419.x. Epub 2011 Jan 25. PubMed PMID: 21545399.
8: Zhang K, Xue N, Yuan Z, Li L, Shi X, Cao L, Du Y. Separation of the two enantiomers of naproxcinod by chiral normal-phase liquid chromatography. J Chromatogr Sci. 2011 Apr;49(4):272-5. PubMed PMID: 21439116.
9: White WB, Schnitzer TJ, Bakris GL, Frayssinet H, Duquesroix B, Weber M. Effects of naproxcinod on blood pressure in patients with osteoarthritis. Am J Cardiol. 2011 May 1;107(9):1338-45. doi: 10.1016/j.amjcard.2010.12.046. Epub 2011 Mar 2. PubMed PMID: 21371681.
10: Björnsson MA, Simonsson US. Modelling of pain intensity and informative dropout in a dental pain model after naproxcinod, naproxen and placebo administration. Br J Clin Pharmacol. 2011 Jun;71(6):899-906. doi: 10.1111/j.1365-2125.2011.03924.x. PubMed PMID: 21272053; PubMed Central PMCID: PMC3099376.
11: Schnitzer TJ, Hochberg MC, Marrero CE, Duquesroix B, Frayssinet H, Beekman M. Efficacy and safety of naproxcinod in patients with osteoarthritis of the knee: a 53-week prospective randomized multicenter study. Semin Arthritis Rheum. 2011 Feb;40(4):285-97. doi: 10.1016/j.semarthrit.2010.06.002. Epub 2010 Sep 9. PubMed PMID: 20828790.
12: Baerwald C, Verdecchia P, Duquesroix B, Frayssinet H, Ferreira T. Efficacy, safety, and effects on blood pressure of naproxcinod 750 mg twice daily compared with placebo and naproxen 500 mg twice daily in patients with osteoarthritis of the hip: a randomized, double-blind, parallel-group, multicenter study. Arthritis Rheum. 2010 Dec;62(12):3635-44. doi: 10.1002/art.27694. PubMed PMID: 20722026.
13: Schnitzer TJ, Kivitz A, Frayssinet H, Duquesroix B. Efficacy and safety of naproxcinod in the treatment of patients with osteoarthritis of the knee: a 13-week prospective, randomized, multicenter study. Osteoarthritis Cartilage. 2010 May;18(5):629-39. doi: 10.1016/j.joca.2009.12.013. Epub 2010 Feb 16. PubMed PMID: 20202489.
14: White WB, Schnitzer TJ, Fleming R, Duquesroix B, Beekman M. Effects of the cyclooxygenase inhibiting nitric oxide donator naproxcinod versus naproxen on systemic blood pressure in patients with osteoarthritis. Am J Cardiol. 2009 Sep 15;104(6):840-5. doi: 10.1016/j.amjcard.2009.05.014. PubMed PMID: 19733721.
15: Karlsson J, Pivodic A, Aguirre D, Schnitzer TJ. Efficacy, safety, and tolerability of the cyclooxygenase-inhibiting nitric oxide donator naproxcinod in treating osteoarthritis of the hip or knee. J Rheumatol. 2009 Jun;36(6):1290-7. doi: 10.3899/jrheum.081011. Epub 2009 May 1. PubMed PMID: 19411388.
16: Geusens P. Naproxcinod, a new cyclooxygenase-inhibiting nitric oxide donator (CINOD). Expert Opin Biol Ther. 2009 May;9(5):649-57. doi: 10.1517/14712590902926071 . Review. PubMed PMID: 19392579.
17: Naproxcinod: AZD 3582, HCT 3012, naproxen nitroxybutylester, nitronaproxen, NO-naproxen. Drugs R D. 2007;8(4):255-8. Review. PubMed PMID: 17596112.