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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2023-02-21 17:18:24 UTC
HMDB IDHMDB0015155
Secondary Accession Numbers
  • HMDB15155
Metabolite Identification
Common NameIsosorbide Mononitrate
DescriptionIsosorbide mononitrate (ISMN), sold under the names Imdur and Monoket, among others, is an organic nitrate used principally in the prophylactic treatment of angina pectoris (ischemic chest pain). ISMN is an active metabolite of isosorbide dinitrate and exerts qualitatively similar effects. Like other organic nitrates, ISMN acts as a prodrug for its active metabolite, nitric oxide, which mediates the therapeutic action of ISMN. Nitric oxide works on both arteries and veins, but predominantly veins. Nitric oxide functions by relaxing veins and reducing the central venous pressure, thereby causing venous pooling and a decrease in the venous return to the heart, thus decreasing cardiac preload (PMID: 31643263 ). The net effect when administering ISMN is therefore a reduced workload for the heart and an improvement in the oxygen supply/demand balance of the myocardium. ISMN is not subject to first pass metabolism in the human liver. Detectable metabolites include isosorbide, sorbitol, and 2-glucuronide of mononitrate, which are pharmacologically inactive (PMID: 1449102 ). Research on ISMN as a cervical ripener to reduce time at hospital to birth is supportive (PMID: 23983763 ). Isosorbide mononitrate is only found in individuals who have consumed or used this drug.
Structure
Data?1676999904
Synonyms
Chemical FormulaC6H9NO6
Average Molecular Weight191.1388
Monoisotopic Molecular Weight191.042987025
IUPAC Name(3R,3aS,6S,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl nitrate
Traditional Namemonit
CAS Registry Number16051-77-7
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 KeyYWXYYJSYQOXTPL-SLPGGIOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurofurans
Sub ClassIsosorbides
Direct ParentIsosorbides
Alternative Parents
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
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point88 - 91 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility57 g/LNot Available
LogP-0.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01020 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01020 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01020
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID25736
KEGG Compound IDC07714
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsosorbide mononitrate
METLIN IDNot Available
PubChem Compound27661
PDB IDNot Available
ChEBI ID6062
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Authors unspecified: Organic Nitrates. 2012. [PubMed:31643263 ]
  2. Abshagen UW: Pharmacokinetics of isosorbide mononitrate. Am J Cardiol. 1992 Nov 27;70(17):61G-66G. doi: 10.1016/0002-9149(92)90028-w. [PubMed:1449102 ]
  3. Yazdizadeh H, Abedi P, Najar S, Angali KA: The impact of isosorbide mononitrate on cervical ripening and labor induction in primiparous women with term pregnancy: A double-blind, randomized, controlled trial. Iran J Nurs Midwifery Res. 2013 May;18(3):246-50. [PubMed:23983763 ]

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 ]