naproxcinod   

GtoPdb Ligand ID: 9551

Synonyms: AZD-3582 | AZD3582 | HCT-3012 | NO-naproxen
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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Physico-chemical Properties
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
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
Classification
Compound class Synthetic organic
Is prodrug? Yes
Active form naproxenNO
IUPAC Name
4-nitrooxybutyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
International Nonproprietary Names
INN number INN
8673 naproxcinod
Synonyms
AZD-3582 | AZD3582 | HCT-3012 | NO-naproxen
Database Links
CAS Registry No. 163133-43-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL2103831
DrugCentral Ligand 4674
GtoPdb PubChem SID 336446937
PubChem CID 9884642
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