This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Nitroaspirin
- DrugBank Accession Number
- DB12445
- Background
Nitroaspirin has been investigated for the treatment of Intermittent Claudication.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Nitroaspirin (DB12445)
- Weight
- Average: 331.28
Monoisotopic: 331.069201763 - Chemical Formula
- C16H13NO7
- Synonyms
- Not Available
- External IDs
- NCX 4016
- NCX-4016
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UProstaglandin G/H synthase 1 inhibitorHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Nitroaspirin may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Nitroaspirin is combined with Abciximab. Abrocitinib The risk or severity of bleeding and thrombocytopenia can be increased when Nitroaspirin is combined with Abrocitinib. Acarbose Nitroaspirin may increase the hypoglycemic activities of Acarbose. Acebutolol Nitroaspirin may decrease the antihypertensive activities of Acebutolol. - Food Interactions
- Not Available
Categories
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antiplatelet agents
- Antirheumatic Agents
- Benzene Derivatives
- Cardiovascular Agents
- Cysteine Proteinase Inhibitors
- Enzyme Inhibitors
- Fibrin Modulating Agents
- Hematologic Agents
- Hydroxybenzoates
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Peripheral Nervous System Agents
- Phenols
- Protease Inhibitors
- Salicylates
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- 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
- Acylsalicylic acid or derivatives / Alkyl nitrate / Allyl-type 1,3-dipolar organic compound / Aromatic homomonocyclic compound / Benzenoid / Benzoate ester / Benzoic acid or derivatives / Benzoyl / Carbonyl group / Carboxylic acid derivative show 15 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- EH04H13L6B
- CAS number
- 175033-36-0
- 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
References
- General References
- 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. [Article]
- Fiorucci S, Del Soldato P: NO-aspirin: mechanism of action and gastrointestinal safety. Dig Liver Dis. 2003 May;35 Suppl 2:S9-19. [Article]
- External Links
- PubChem Compound
- 119032
- PubChem Substance
- 347828686
- ChemSpider
- 106359
- ChEBI
- 125482
- ChEMBL
- CHEMBL374385
- ZINC
- ZINC000000022315
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Completed Treatment Intermittent Claudication 1 2 Terminated Prevention Early Nephropathy / Type 2 Diabetes Mellitus 1
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
Property Value Source Water Solubility 0.00402 mg/mL ALOGPS logP 3.04 ALOGPS logP 3.17 Chemaxon logS -4.9 ALOGPS pKa (Strongest Basic) -6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 104.97 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 81.5 m3·mol-1 Chemaxon Polarizability 31.6 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00di-4910000000-fb967ddff95ce7bd84eb Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 169.8713 predictedDeepCCS 1.0 (2019) [M+H]+ 173.89098 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.70604 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
Drug created at October 20, 2016 22:25 / Updated at June 12, 2020 16:53