Structure via PubChem · Public domain (PubChem)
naproxcinod
Sign in to saveAlso known as AZD3582, (S)-2-(6-Methoxy-2-naphthyl)propanoic acid 4-nitrooxybutyl ester, HCT 3012, Nitronaproxen, AZD 3582, Naproxen-N-butyl nitrate
Naproxcinod (nitronaproxen) is a nonsteroidal anti-inflammatory drug (NSAID) developed by the French pharmaceutical company NicOx. It is a derivative of naproxen with a nitroxybutyl ester to allow it to also act as a nitric oxide (NO) donor. This second mechanism of action makes naproxcinod the first in a new class of drugs, the cyclooxygenase inhibiting nitric oxide donators (CINODs), that are hoped to produce similar analgesic efficacy to traditional NSAIDs, but with less gastrointestinal and cardiovascular side effects.
Chemical data
- Formula
- C18H21NO6
- Molecular weight
- 347.4 g/mol
- IUPAC name
- 4-nitrooxybutyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
- SMILES
- C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)OCCCCO[N+](=O)[O-]
- InChIKey
- AKFJWRDCWYYTIG-ZDUSSCGKSA-N
- XLogP
- 4.1
- Polar surface area
- 90.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- rheumatic disease, liver disease, osteoarthritis, hip, kidney failure
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 347.136887
Show 5 more facts
- chemical formula
- C₁₈H₂₁NO₆
- canonical SMILES
- CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)OCCCCO[N+](=O)[O-]
- isomeric SMILES
- C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)OCCCCO[N+](=O)[O-]
- World Health Organisation international non-proprietary name
- naproxcinod
- Commons category
- Naproxcinod
Sources (2)
via Wikidata · CC0
~5 min read
Encyclopedic overview
10 sectionsContents
- Current situation in pain treatment
- Proposed indications
- Mechanism of action
- Safety profile
- Blood pressure profile
- Clinical relevance of small increase in blood pressure
- Gastrointestinal safety
- Commercialization
- See also
- References
Naproxcinod (nitronaproxen) is a nonsteroidal anti-inflammatory drug (NSAID) developed by the French pharmaceutical company NicOx. It is a derivative of naproxen with a nitroxybutyl ester to allow it to also act as a nitric oxide (NO) donor. This second mechanism of action makes naproxcinod the first in a new class of drugs, the cyclooxygenase inhibiting nitric oxide donators (CINODs), that are hoped to produce similar analgesic efficacy to traditional NSAIDs, but with less gastrointestinal and cardiovascular side effects.
In December 2006, Scientific American distinguished naproxcinod as one of the ten most promising treatments for the world's biggest health threats. However, in 2010 the U.S. Food and Drug Administration determined that further clinical trials would be needed to obtain approval.
Excerpted from Wikipedia’s “naproxcinod” article, available under the CC BY-SA 4.0 licence.