4-(NITROOXY)BUTYL (2S)-2-(6-METHOXY-2-NAPHTHYL)PROPANOATE
4-(NITROOXY)BUTYL (2S)-2-(6-METHOXY-2-NAPHTHYL)PROPANOATE Basic information
- Product Name:
- 4-(NITROOXY)BUTYL (2S)-2-(6-METHOXY-2-NAPHTHYL)PROPANOATE
- Synonyms:
-
- 4-(NITROOXY)BUTYL (2S)-2-(6-METHOXY-2-NAPHTHYL)PROPANOATE
- NAPROXCINOD
- (S)-2-(6-Methoxy-2-naphthyl)propanoic acid 4-nitrooxybutyl ester
- Nitronaproxen
- AZD 3582
- HCT 3012
- NAPROXCINOD INTERMEDIATES
- AKFJWRDCWYYTIG-ZDUSSCGKSA-N
- CAS:
- 163133-43-5
- MF:
- C18H21NO6
- MW:
- 347.36
- Mol File:
- 163133-43-5.mol
4-(NITROOXY)BUTYL (2S)-2-(6-METHOXY-2-NAPHTHYL)PROPANOATE Chemical Properties
- Boiling point:
- 489.5±30.0 °C(Predicted)
- Density
- 1.213
4-(NITROOXY)BUTYL (2S)-2-(6-METHOXY-2-NAPHTHYL)PROPANOATE Usage And Synthesis
Uses
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].
Definition
ChEBI: A carboxylic ester obtained by formal condensation of the carboxy group of naproxen with the hydroxy group of 4-(nitrooxy)butanol. A cyclooxygenase-inhibiting nitric oxide donator that is metabolised to naproxen and a nitric oxide donating moiety, effectiv in treatment of osteoarthritis.
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. DOI:10.1016/j.ejps.2003.10.020
[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. DOI:10.1016/j.ejps.2005.02.015
[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. DOI:10.1093/hmg/ddu033
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