naproxcinod

Names

[ CAS No. ]:
163133-43-5

[ Name ]:
naproxcinod

[Synonym ]:
Naproxcinod
2-(S)-(6-methoxy-2-naphthyl)-propanoic acid 4-nitroxybutyl ester
HCT-3012
2-(S)-(6-methoxy-2-naphthyl)-propanoic acid nitrooxybutyl ester
4-nitrooxybutyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
Nitronaproxen
2-(S)-(6-methoxy-2-naphthyl)propanoic acid 4-(nitrooxy)butyl ester
AZD-3582
(S)-2-(6-methoxy-2-naphthyl)propionic acid 4-nitrooxybutyl ester
naproxen-n-butyl nitrate

Biological Activity

[Description]:

Naproxcinod (Nitronaproxen) is the first in class of cyclooxygenase (COX)-inhibiting nitric oxide donators (CINODs). Naproxcinod shows analgesic and anti-inflammatory effects, it can be used for the research of osteoarthritis and inflammation[1][2][3].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Inflammation/Immunology

[In Vitro]

Naproxcinod (1-30 μM; 15 min) concentration-dependently increases cGMP level up to 27-fold over basal level[1]. Naproxcinod (1-100 μM; 8 h) concentration-dependently increases HO-1 mRNA in endothelial cells[2]. Western Blot Analysis[2] Cell Line: Endothelial and gastric mucosal cell lines Concentration: 30-1000 μM Incubation Time: 8 and 24 hours Result: Increased HO-1 protein levels in endothelial and gastric mucosal cells and increased HO-1mRNA levels in endothelial cells.

[In Vivo]

Naproxcinod (0-41 mg/kg; p.o. once daily for 42 weeks) shows a significantly higher mean BW (7.3%) than vehicle group and improves skeletal and cardiac disease phenotype in the mouse model of DMD[3]. Animal Model: C57BL/10 mice with Duchenne muscular dystrophy (DMD)[3] Dosage: 0, 10, 21 and 41 mg/kg Administration: Oral gavage; 0-41 mg/kg once daily for 42 weeks Result: Significantly improved fraction shortening and ejection fraction, and reduced inflammation in vivo.

[References]

[1]. Berndt G, et al. A common pathway of nitric oxide release from AZD3582 and glyceryl trinitrate. Eur J Pharm Sci. 2004 Feb;21(2-3):331-5.

[2]. Berndt G, et al. AZD3582 increases heme oxygenase-1 expression and antioxidant activity in vascular endothelial and gastric mucosal cells. Eur J Pharm Sci. 2005 Jun;25(2-3):229-35.

[3]. Uaesoontrachoon K, et al. 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.

Chemical & Physical Properties

[ Density]:
1.213

[ Boiling Point ]:
489.475ºC at 760 mmHg

[ Molecular Formula ]:
C18H21NO6

[ Molecular Weight ]:
347.36200

[ Flash Point ]:
193.208ºC

[ Exact Mass ]:
347.13700

[ PSA ]:
90.58000

[ LogP ]:
4.00680

Synthetic Route

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Precursor & DownStream

Precursor

DownStream