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Isosorbide Mononitrate

July 24, 2017
Common Name

Isosorbide Mononitrate Description

Isosorbide mononitrate is a drug used principally in the treatment of angina pectoris[1] and acts by dilating the blood vessels so as to reduce the blood pressure. It is sold by AstraZeneca under the trade name Imdur. Isosorbide mononitrate is used to for the the prophylactic treatment of angina pectoris; that is, it is taken in order to prevent or at least reduce the occurrence of angina. Research on Isosorbide mononitrate as a cervical ripener to reduce time at hospital to birth is supportive. Isosorbide mononitrate is an active metabolite of isosorbide dinitrate and exerts qualitatively similar effects. Isosorbide mononitrate reduces the workload of the heart by producing venous and arterial dilation. By reducing the end diastolic pressure and volume, isosorbide mononitrate lowers intramural pressure, hence leading to an improvement in the subendocardial blood flow. The net effect when administering isosorbide mononitrate is therefore a reduced workload for the heart and an improvement in the oxygen supply/demand balance of the myocardium. The adverse reactions which follow have been reported in studies with isosorbide mononitrate: Very common: Headache predominates (up to 30%) necessitating withdrawal of 2 to 3 % of patients, but the incidence reduces rapidly as treatment continues. Common: Tiredness, sleep disturbances (6%) and gastrointestinal disturbances (6%) have been reported during clinical trials with isosorbide mononitrate modified release tablets, but at a frequency no greater than for placebo. Hypotension (4 to 5%), poor appetite (2.5%), nausea (1%). Adverse effects associated with the clinical use of the drug are as expected with all nitrate preparations. They occur mainly in the early stages of treatment. Hypotension (4%) with symptoms such as dizziness and nausea (1%) have been reported. These symptoms generally disappear during long-term treatment. Other reactions that have been reported with isosorbide mononitrate modified release tablets include tachycardia, vomiting, diarrhoea, vertigo and heartburn. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source CoranginChEBI DurideChEBI ElantanChEBI ImdurChEBI ImtrateChEBI IsmexinChEBI IsmoChEBI IsmoxChEBI Isosorbidi mononitrasChEBI MedocorChEBI MonicorChEBI mono CoraxChEBI MonocedocardChEBI MonocordChEBI Monodur durliesChEBI MonoketChEBI MonolongChEBI MonomaxChEBI MononitChEBI Mononitrate d'isosorbideChEBI mononitrato De isosorbidaChEBI MonoprontChEBI Monosorb XL 60ChEBI MonosorbitrateChEBI MonosordilChEBI NitraminChEBI OlicardChEBI OrasorbilChEBI PertilChEBI PromocardChEBI SigacoraChEBI SorbimonChEBI TurimonitChEBI UniketChEBI VasdilatChEBI Isosorbide mononitric acidGenerator Imtric acidGenerator Mononitric acid d'isosorbideGenerator Monosorbitric acidGenerator IHDHMDB ISMNHMDB 5-ISMNMeSH MonizidMeSH Isosorbide-5-mononitrateMeSH MonocinqueMeSH 5-ISMN durliesMeSH Olicard-retardMeSH mono Mac 50DMeSH Olicard 40MeSH Isosorbide-5-nitrateMeSH

Chemical Formlia

C6H9NO6 Average Molecliar Weight

191.1388 Monoisotopic Molecliar Weight

191.042987025 IUPAC Name

(3R,3aS,6S,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl nitrate Traditional Name

monit CAS Registry Number

16051-77-7 SMILES

[H][C@]12OC[C@@H](O[N+]([O-])=O)[C@@]1([H])OC[C@@H]2O

InChI Identifier

InChI=1S/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5+,6+/m0/s1

InChI Key

YWXYYJSYQOXTPL-SLPGGIOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Furofurans Sub Class

Isosorbides Direct Parent

Isosorbides Alternative Parents

  • Tetrahydrofurans
  • Alkyl nitrates
  • Secondary alcohols
  • Organic nitro compounds
  • Organic nitric acids and derivatives
  • Oxacyclic compounds
  • Dialkyl ethers
  • Organic zwitterions
  • Organic oxides
  • Organic nitrogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Isosorbide
  • Organic nitrate
  • Tetrahydrofuran
  • Alkyl nitrate
  • Organic nitric acid or derivatives
  • Secondary alcohol
  • Organic nitro compound
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic zwitterion
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound

    • Molecliar Framework

    Aliphatic heteropolycyclic compounds External Descriptors

  • nitrate ester (CHEBI:6062 )
  • glucitol derivative (CHEBI:6062 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Nitrates and Nitrites
  • Nitric Oxide Donors
  • Vasodilator Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point88 – 91 °CNot Available Boiling PointNot AvailableNot Available Water Solubility5.70e+01 g/LNot Available LogP-0.9Not Available

    Predicted Properties

    Property Value Source Water Solubility57.0 mg/mLALOGPS logP-0.74ALOGPS logP-0.48ChemAxon logS-0.53ALOGPS pKa (Strongest Acidic)13.34ChemAxon pKa (Strongest Basic)-3.5ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area93.74 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity38.08 m3·mol-1ChemAxon Polarizability15.85 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01020

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01020

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01020 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    25736 KEGG Compound ID

    C07714 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Isosorbide_mononitrate NuGOwiki Link

    HMDB15155 Metagene Link

    HMDB15155 METLIN ID

    Not Available PubChem Compound

    27661 PDB ID

    Not Available ChEBI ID

    6062

    Product: Metoprolol

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
    General function:
    Involved in phosphorus-oxygen lyase activity
    Specific function:
    Has guanylyl cyclase on binding to the beta-1 subunit.Isoform 2 acts as a negative regulator of guanylyl cyclase activity as it forms non-functional heterodimers with the beta subunits.
    Gene Name:
    GUCY1A2
    Uniprot ID:
    P33402
    Molecular weight:
    81749.185
    References
    1. Moncada S, Palmer RM, Higgs EA: Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol Rev. 1991 Jun;43(2):109-42. [PubMed:1852778 ]
    2. Mancuso C, Navarra P, Preziosi P: Roles of nitric oxide, carbon monoxide, and hydrogen sulfide in the regulation of the hypothalamic-pituitary-adrenal axis. J Neurochem. 2010 May;113(3):563-75. doi: 10.1111/j.1471-4159.2010.06606.x. Epub 2010 Jan 20. [PubMed:20089135 ]

    PMID: 11877444

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