Details of the Drug

General Information of Drug (ID: DMOX1CU)

Drug Name
NCX-4016
Synonyms
Nitroaspirin; Ncx 4016; NO-ASA; Nitric oxide-releasing aspirin; M-NO-ASA; M-NO-aspirin; [3-(nitrooxymethyl)phenyl] 2-acetyloxybenzoate; Benzoic acid, 2-(acetyloxy)-, 2-((nitrooxy)methyl)phenyl ester; Benzoic acid, 2-(acetyloxy)-, 3-((nitrooxy)methyl)phenyl ester; 2-((Nitrooxy)methyl)phenyl 2-(acetyloxy)benzoate; 2-Acetoxybenzoate-2-(1-nitroxymethyl)phenyl ester; 2-Acetoxybenzoic acid 3-(nitrooxymethyl)phenyl ester; 2-Acetoxybenzoic acid 3-nitrooxymethylphenyl ester; 3-((Nitrooxy)methyl)phenyl 2-(acetyloxy)benzoate; 3-(Nitroxymethyl)phenyl 2-acetoxybenzoate
Indication
Disease Entry ICD 11 Status REF
Inflammation 1A00-CA43.1 Phase 2 [1]
Claudication FA11 Discontinued in Phase 2 [2]
Nephropathy GC2Z Discontinued in Phase 2 [2]
Type-2 diabetes 5A11 Discontinued in Phase 2 [2]
Therapeutic Class
Analgesics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 331.28
Logarithm of the Partition Coefficient (xlogp) 2.9
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 7
Chemical Identifiers
Formula
C16H13NO7
IUPAC Name
[3-(nitrooxymethyl)phenyl] 2-acetyloxybenzoate
Canonical SMILES
CC(=O)OC1=CC=CC=C1C(=O)OC2=CC=CC(=C2)CO[N+](=O)[O-]
InChI
InChI=1S/C16H13NO7/c1-11(18)23-15-8-3-2-7-14(15)16(19)24-13-6-4-5-12(9-13)10-22-17(20)21/h2-9H,10H2,1H3
InChIKey
IOJUJUOXKXMJNF-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
119032
ChEBI ID
CHEBI:125482
CAS Number
175033-36-0
UNII
EH04H13L6B
DrugBank ID
DB12445
TTD ID
D05OQX
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase (COX) TTK0943 PGH1_HUMAN ; PGH2_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apolipoprotein A-I (APOA1) OT5THARI APOA1_HUMAN Gene/Protein Processing [3]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [4]
Cyclic AMP-dependent transcription factor ATF-2 (ATF2) OTNIZPEA ATF2_HUMAN Post-Translational Modifications [5]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [5]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [5]
RAC-alpha serine/threonine-protein kinase (AKT1) OT8H2YY7 AKT1_HUMAN Post-Translational Modifications [5]
Serum paraoxonase/arylesterase 1 (PON1) OTD0Z2XO PON1_HUMAN Gene/Protein Processing [3]
Transcription factor 4 (TCF4) OTB9ASTK ITF2_HUMAN Gene/Protein Processing [6]
Transcription factor Jun (JUN) OTCYBO6X JUN_HUMAN Post-Translational Modifications [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Direct and irreversible inhibition of cyclooxygenase-1 by nitroaspirin (NCX 4016). J Pharmacol Exp Ther. 2005 Dec;315(3):1331-7.
2 Emerging drugs in peripheral arterial disease. Expert Opin Emerg Drugs. 2006 Mar;11(1):75-90.
3 Induction of paraoxonase 1 and apolipoprotein A-I gene expression by aspirin. J Lipid Res. 2008 Oct;49(10):2142-8.
4 NO-releasing aspirin exerts stronger growth inhibitory effect on Barrett's adenocarcinoma cells than traditional aspirin. J Physiol Pharmacol. 2006 Dec;57 Suppl 12:15-24.
5 Nitric oxide-donating aspirin inhibits colon cancer cell growth via mitogen-activated protein kinase activation. J Pharmacol Exp Ther. 2006 Jan;316(1):25-34. doi: 10.1124/jpet.105.091363. Epub 2005 Sep 16.
6 Nitro-aspirin inhibits MCF-7 breast cancer cell growth: effects on COX-2 expression and Wnt/beta-catenin/TCF-4 signaling. Biochem Pharmacol. 2009 Nov 15;78(10):1298-304.