naproxcinod   Click here for help

GtoPdb Ligand ID: 9551

Synonyms: AZD-3582 | AZD3582 | HCT-3012 | NO-naproxen
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Naproxcinod is a NO-donating naproxen analogue prodrug. It is the first in a new class of anti-inflammatory and analgesic drugs known as cyclooxygenase-inhibiting nitric oxide donors (CINODs) [2], that are designed to lessen the gastrointestinal (and cardiovascular) side-effects of traditional NSAIDs. The NO released by the prodrug mediates this beneficial effect.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 10
Topological polar surface area 87.9
Molecular weight 347.14
XLogP 4.12
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES COc1ccc2c(c1)ccc(c2)C(C(=O)OCCCCO[N+](=O)[O-])C
Isomeric SMILES COc1ccc2c(c1)ccc(c2)[C@@H](C(=O)OCCCCO[N+](=O)[O-])C
InChI 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
InChI Key AKFJWRDCWYYTIG-ZDUSSCGKSA-N
References
1. Baerwald C, Verdecchia P, Duquesroix B, Frayssinet H, Ferreira T. (2010)
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, 62 (12): 3635-44. [PMID:20722026]
2. Geusens P. (2009)
Naproxcinod, a new cyclooxygenase-inhibiting nitric oxide donator (CINOD).
Expert Opin Biol Ther, 9 (5): 649-57. [PMID:19392579]
3. Hawkey CJ, Jones JI, Atherton CT, Skelly MM, Bebb JR, Fagerholm U, Jonzon B, Karlsson P, Bjarnason IT. (2003)
Gastrointestinal safety of AZD3582, a cyclooxygenase inhibiting nitric oxide donator: proof of concept study in humans.
Gut, 52 (11): 1537-42. [PMID:14570719]
4. Miglietta D, De Palma C, Sciorati C, Vergani B, Pisa V, Villa A, Ongini E, Clementi E. (2015)
Naproxcinod shows significant advantages over naproxen in the mdx model of Duchenne Muscular Dystrophy.
Orphanet J Rare Dis, 10: 101. [PMID:26296873]
5. Schnitzer TJ, Hochberg MC, Marrero CE, Duquesroix B, Frayssinet H, Beekman M. (2011)
Efficacy and safety of naproxcinod in patients with osteoarthritis of the knee: a 53-week prospective randomized multicenter study.
Semin Arthritis Rheum, 40 (4): 285-97. [PMID:20828790]