Naproxcinod

Names

[ 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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.