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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEMBL125482
CAS Number: 175033-36-0
UNII: EH04H13L6B
DrugBank ID: DB12445
TTD ID: D05OQX

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Repurposed Drugs (RPD)

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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
Cyclic AMP-dependent transcription factor ATF-2 (ATF2)	OTNIZPEA	ATF2_HUMAN	Post-Translational Modifications	[3]
Mitogen-activated protein kinase 1 (MAPK1)	OTH85PI5	MK01_HUMAN	Post-Translational Modifications	[3]
Mitogen-activated protein kinase 3 (MAPK3)	OTCYKGKO	MK03_HUMAN	Post-Translational Modifications	[3]
Transcription factor 4 (TCF4)	OTB9ASTK	ITF2_HUMAN	Gene/Protein Processing	[4]
Transcription factor Jun (JUN)	OTCYBO6X	JUN_HUMAN	Post-Translational Modifications	[3]

Molecular Interaction Atlas (MIA)

MIA Detail

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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	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.
4	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.