You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:40:48 UTC
HMDB IDHMDB0015021
Secondary Accession Numbers
  • HMDB15021
Metabolite Identification
Common NameIsosorbide Dinitrate
DescriptionIsosorbide Dinitrate is only found in individuals that have used or taken this drug. It is a vasodilator used in the treatment of angina pectoris. Its actions are similar to nitroglycerin but with a slower onset of action. [PubChem]Similar to other nitrites and organic nitrates, isosorbide dinitrate is converted to nitric oxide (NO), an active intermediate compound which activates the enzyme guanylate cyclase (atrial natriuretic peptide receptor A). This stimulates the synthesis of cyclic guanosine 3',5'-monophosphate (cGMP) which then activates a series of protein kinase-dependent phosphorylations in the smooth muscle cells, eventually resulting in the dephosphorylation of the myosin light chain of the smooth muscle fiber. The subsequent release of calcium ions results in the relaxation of the smooth muscle cells and vasodilation.
Structure
Data?1582753248
Synonyms
ValueSource
1,4:3,6-Dianhydrosorbitol 2,5-dinitrateChEBI
CarvasinChEBI
Cedocard retardChEBI
D-Isosorbide dinitrateChEBI
Dianhydrosorbitol 2,5-dinitrateChEBI
Dinitrate d'isosorbideChEBI
Dinitrato de isosorbidaChEBI
DinitroisosorbideChEBI
DinitrosorbideChEBI
FlindixChEBI
IsoketChEBI
IsorbidChEBI
IsordilChEBI
Isosorbide 2,5-dinitrateChEBI
Isosorbidi dinitrasChEBI
NitrosorbideChEBI
Sorbide nitrateChEBI
SorbidilatChEBI
SorbidnitrateChEBI
Dilatrate-SRKegg
1,4:3,6-Dianhydrosorbitol 2,5-dinitric acidGenerator
D-Isosorbide dinitric acidGenerator
Dianhydrosorbitol 2,5-dinitric acidGenerator
Dinitric acid d'isosorbideGenerator
Isosorbide 2,5-dinitric acidGenerator
Sorbide nitric acidGenerator
Sorbidnitric acidGenerator
Dilatric acid-SRGenerator
Isosorbide dinitric acidGenerator
Sorbide, dinitrateHMDB
DilatrateHMDB
Iso-bidHMDB
Isoket retard 120HMDB
Isoket retard-120HMDB
IsotrateHMDB
Cardonit 40HMDB
Iso bidHMDB
SorbitrateHMDB
Dinitrate, isosorbideHMDB
Isoket retard120HMDB
Isomak RHMDB
SorbonitHMDB
IsoBidHMDB
IsodinitHMDB
Chemical FormulaC6H8N2O8
Average Molecular Weight236.1363
Monoisotopic Molecular Weight236.028065242
IUPAC Name(3S,3aS,6R,6aS)-6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl nitrate
Traditional Name(3S,3aS,6R,6aS)-6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl nitrate
CAS Registry Number87-33-2
SMILES
[H][C@]12OC[C@H](O[N+]([O-])=O)[C@@]1([H])OC[C@H]2O[N+]([O-])=O
InChI Identifier
InChI=1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1
InChI KeyMOYKHGMNXAOIAT-JGWLITMVSA-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
  • Organic nitro compound
  • Dialkyl ether
  • Ether
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Oxacycle
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point70 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.94 g/LNot Available
LogP1.31HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.94 g/LALOGPS
logP0.87ALOGPS
logP0.44ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area128.56 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity44.77 m³·mol⁻¹ChemAxon
Polarizability18.07 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9410000000-92c2931ba576380c836cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-4ac5c9f364014be4b5edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0490000000-296d2bcb699d8eeed9ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-1c95dd82e8ca93a68ef4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-2890000000-b3fc1aa7995241f9c8c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0076-1960000000-482b81af13a797c89c89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-4900000000-3c42a9008364f7f3fe6bSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00883 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00883 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00883
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6619
KEGG Compound IDC07456
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsosorbide dinitrate
METLIN IDNot Available
PubChem Compound6883
PDB IDNot Available
ChEBI ID6061
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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:
Receptor for the atrial natriuretic peptide NPPA/ANP and the brain natriuretic peptide NPPB/BNP which are potent vasoactive hormones playing a key role in cardiovascular homeostasis. Has guanylate cyclase activity upon binding of the ligand.
Gene Name:
NPR1
Uniprot ID:
P16066
Molecular weight:
118918.11
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Villarroya M, Lopez MG, de Pascual R, Garcia AG: Preclinical profile of PF9404C, a nitric oxide donor with beta receptor blocking properties. Cardiovasc Drug Rev. 2005 Summer;23(2):149-60. [PubMed:16007231 ]
  4. Takabuchi S, Hirota K, Nishi K, Oda S, Oda T, Shingu K, Takabayashi A, Adachi T, Semenza GL, Fukuda K: The inhibitory effect of sodium nitroprusside on HIF-1 activation is not dependent on nitric oxide-soluble guanylyl cyclase pathway. Biochem Biophys Res Commun. 2004 Nov 5;324(1):417-23. [PubMed:15465035 ]
  5. Beauregard C, Brandt PC, Chiou GC: Nitric oxide and cyclic GMP-mediated protein secretion from cultured lacrimal gland acinar cells. J Ocul Pharmacol Ther. 2002 Oct;18(5):429-43. [PubMed:12419094 ]
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
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 ]