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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form naproxen, NO
IUPAC Name Click here for help
4-nitrooxybutyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
International Nonproprietary Names Click here for help
INN number INN
8673 naproxcinod
Synonyms Click here for help
AZD-3582 | AZD3582 | HCT-3012 | NO-naproxen
Database Links Click here for help
CAS Registry No. 163133-43-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL2103831
DrugCentral Ligand 4674
GtoPdb PubChem SID 336446937
PubChem CID 9884642
Search Google for chemical match using the InChIKey AKFJWRDCWYYTIG-ZDUSSCGKSA-N
Search Google for chemicals with the same backbone AKFJWRDCWYYTIG
Search PubMed clinical trials naproxcinod
Search PubMed titles naproxcinod
Search PubMed titles/abstracts naproxcinod
UniChem Compound Search for chemical match using the InChIKey AKFJWRDCWYYTIG-ZDUSSCGKSA-N
UniChem Connectivity Search for chemical match using the InChIKey AKFJWRDCWYYTIG-ZDUSSCGKSA-N