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
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
No information available.
Summary of Clinical Use Click here for help
Proof-of-concept in humans is reported in [3]. The EMA granted naproxcinod orphan designation for the treatment of Duchenne muscular dystrophy [4] in 2013, followed by the US FDA in 2015. Phase 3 studies comparing naproxcinod with naproxen or placebo in patients with osteoarthritis of the hip and knee have been completed [1,5].