This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Nitroaspirin
Accession Number
DB12445  (DB05822)
Type
Small Molecule
Groups
Investigational
Description

Nitroaspirin has been investigated for the treatment of Intermittent Claudication.

Structure
Thumb
Synonyms
Not Available
External IDs
NCX 4016 / NCX-4016
Categories
UNII
EH04H13L6B
CAS number
175033-36-0
Weight
Average: 331.28
Monoisotopic: 331.069201763
Chemical Formula
C16H13NO7
InChI Key
IOJUJUOXKXMJNF-UHFFFAOYSA-N
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
IUPAC Name
3-[(nitrooxy)methyl]phenyl 2-(acetyloxy)benzoate
SMILES
CC(=O)OC1=CC=CC=C1C(=O)OC1=CC=CC(CO[N+]([O-])=O)=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProstaglandin G/H synthase 1
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Nitroaspirin.
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with 16-Bromoepiandrosterone.
19-norandrostenedioneThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with 19-norandrostenedione.
5-androstenedioneThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with 5-androstenedione.
AcarboseNitroaspirin may increase the hypoglycemic activities of Acarbose.
AcebutololNitroaspirin may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with Acemetacin.
AcenocoumarolNitroaspirin may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenNitroaspirin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. Tesei A, Ricotti L, Ulivi P, Medri L, Amadori D, Zoli W: NCX 4016, a nitric oxide-releasing aspirin derivative, exhibits a significant antiproliferative effect and alters cell cycle progression in human colon adenocarcinoma cell lines. Int J Oncol. 2003 Jun;22(6):1297-302. [PubMed:12738997]
  2. Fiorucci S, Del Soldato P: NO-aspirin: mechanism of action and gastrointestinal safety. Dig Liver Dis. 2003 May;35 Suppl 2:S9-19. [PubMed:12846439]
External Links
PubChem Compound
119032
PubChem Substance
347828686
ChemSpider
106359
ChEBI
125482
ChEMBL
CHEMBL374385

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentIntermittent Claudication1
2TerminatedPreventionEarly Nephropathy / Type 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00402 mg/mLALOGPS
logP3.04ALOGPS
logP3.17ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area104.97 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity81.5 m3·mol-1ChemAxon
Polarizability31.6 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Depsides and depsidones
Sub Class
Not Available
Direct Parent
Depsides and depsidones
Alternative Parents
Acylsalicylic acids and derivatives / Phenol esters / Benzoic acid esters / Phenoxy compounds / Benzoyl derivatives / Dicarboxylic acids and derivatives / Alkyl nitrates / Organic nitro compounds / Organic nitric acids and derivatives / Carboxylic acid esters
show 4 more
Substituents
Depside backbone / Acylsalicylic acid or derivatives / Benzoate ester / Phenol ester / Benzoic acid or derivatives / Phenoxy compound / Benzoyl / Monocyclic benzene moiety / Benzenoid / Dicarboxylic acid or derivatives
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Gresele P, Momi S: Pharmacologic profile and therapeutic potential of NCX 4016, a nitric oxide-releasing aspirin, for cardiovascular disorders. Cardiovasc Drug Rev. 2006 Summer;24(2):148-68. [PubMed:16961726]
  2. Corazzi T, Leone M, Maucci R, Corazzi L, Gresele P: Direct and irreversible inhibition of cyclooxygenase-1 by nitroaspirin (NCX 4016). J Pharmacol Exp Ther. 2005 Dec;315(3):1331-7. doi: 10.1124/jpet.105.089896. Epub 2005 Sep 6. [PubMed:16144976]

Drug created on October 20, 2016 16:25 / Updated on October 01, 2018 15:14