Identification

Name
Isosorbide mononitrate
Accession Number
DB01020  (APRD00528)
Type
Small Molecule
Groups
Approved
Description

Isosorbide mononitrate is an organic nitrate with vasodilating properties. It is an anti-anginal agent that works by relaxing the smooth muscles of both arteries and veins, but but predominantly veins to reduce cardiac preload.4,7 Isosorbide mononitrate is an active metabolite of isosorbide dinitrate. Like other organic nitrates, isosorbide mononitrate acts as a prodrug for its active metabolite, nitric oxide, which mediates the therapeutic action of isosorbide mononitrate.7 Isosorbide mononitrate has a longer duration of action than nitroglycerin due to its slow onset of absorption and metabolism.3

First approved by the FDA in 1991,7 isosorbide mononitrate is used for the prevention and management of angina pectoris caused by coronary artery disease; however, the onset of action of orally-administered isosorbide mononitrate is not rapid enough to offset an acute anginal episode.4 It is available in oral tablets generically and under the brand name ISMO and Monoket. The extended-release forms of the drug are also available generically and under the brand name Imdur.7

Structure
Thumb
Synonyms
  • IS 5-MN
  • IS-5-MN
  • IS-5MN
  • ISMN
  • Iso-5-mononitrate
  • Isosorbide 5-mononitrate
  • Isosorbide 5-nitrate
  • Isosorbide mononitrate
  • Isosorbide-5-mononitrate
  • Isosorbidi mononitras
  • Mononitrate d'isosorbide
  • Mononitrato de isosorbida
  • Monosorbitrate
External IDs
AHR-4698 / BM 22.145 / BM-22.145 / BM-22145
Active Moieties
NameKindUNIICASInChI Key
IsosorbideunknownWXR179L51S652-67-5KLDXJTOLSGUMSJ-JGWLITMVSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ImdurTablet, extended release60 mgOralMda Inc.1994-12-31Not applicableCanada
ImdurTablet120 mg/1OralSchering Corporation2003-09-012006-11-30Us
ImdurTablet60 mg/1OralSchering Corporation2003-09-012006-10-31Us
ImdurTablet30 mg/1OralSchering Corporation2003-09-012006-10-31Us
IsmnTablet, extended releaseOralSivem Pharmaceuticals Ulc2015-10-082017-06-27Canada
IsmoTablet, film coated20 mg/1OralReddy Pharmaceuticals, LLC2007-03-31Not applicableUs
Ismo Tab 20mgTabletOralWyeth Ayerst Canada Inc.1994-12-312002-06-10Canada
MonoketTablet20 mg/1OralLannett Company, Inc.1993-06-30Not applicableUs
MonoketTablet10 mg/1OralLannett Company, Inc.1993-06-30Not applicableUs
MonoketTablet20 mg/1OralUcb Inc1993-06-302012-07-30Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-ismnTablet, extended releaseOralApotex Corporation2006-03-03Not applicableCanada
Dom-ismnTablet, extended releaseOralDominion PharmacalNot applicableNot applicableCanada
ImdurTablet, extended release120 mg/1OralSchering Corporation2006-01-052017-04-06Us
ImdurTablet, extended release60 mg/1OralSchering Corporation2006-01-052017-04-06Us
ImdurTablet, extended release60 mg/1OralPhysicians Total Care, Inc.1997-01-032012-06-30Us
ImdurTablet, extended release30 mg/1OralSchering Corporation2006-01-052017-04-06Us
ImdurTablet, extended release30 mg/1OralPhysicians Total Care, Inc.2009-12-022012-06-30Us
Isorsorbide MononitrateTablet, film coated, extended release60 mg/1OralActavis Pharma Company2005-05-042006-07-30Us
Isorsorbide MononitrateTablet, film coated, extended release30 mg/1OralActavis Pharma Company2005-05-042006-07-30Us
IsosorbideTablet, film coated, extended release30 mg/1OralCarilion Materials Management2006-03-30Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
International/Other Brands
Chemydur / Corangin / Dilatrate / Duride / Elantan / Etimonis / Imodur / Imtrate / Ismexin / Ismox / Isomon / Isomonit / Isonorm / Medocor / Monicor / Monit / Mono Corax / Mono Mack / Monocedocard / Monoclair / Monocord / Monodur Durules / Monolong / Monomax / Mononit / Monopront / Monosorb / Monosordil / Monotrate / Nitramin / Olicard / Olicardin / Orasorbil / Pertil / Plodin / Promocard / Sigacora / Solotrate / Sorbimon / Turimonit / Uniket / Vasdilat
Categories
UNII
LX1OH63030
CAS number
16051-77-7
Weight
Average: 191.1388
Monoisotopic: 191.042987025
Chemical Formula
C6H9NO6
InChI Key
YWXYYJSYQOXTPL-SLPGGIOYSA-N
InChI
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
IUPAC Name
(3R,3aS,6S,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl nitrate
SMILES
[H][C@]12OC[C@@H](O[N+]([O-])=O)[C@@]1([H])OC[C@@H]2O

Pharmacology

Indication

Isosorbide mononitrate is indicated for the prevention and management of angina pectoris due to coronary artery disease. The onset of action of oral isosorbide mononitrate is not sufficiently rapid to be useful in aborting an acute anginal episode.4

Associated Conditions
Pharmacodynamics

Isosorbide mononitrate is an anti-anginal agent and vasodilator that relaxes vascular smooth muscle to prevent and manage angina pectoris. The pharmacological action is mediated by the active metabolite, nitric oxide, which is released when isosorbide mononitrate is metabolized.3 Nitric oxide works on both arteries and veins, but predominantly veins: by relaxing veins and reducing the central venous pressure, nitric oxide causes venous pooling and a decrease in the venous return to the heart, thus decreasing cardiac preload.7 In healthy subjects, the stroke volume is decreased and venous pooling can occur in the standing posture, leading to postural hypotension and dizziness.3

At therapeutic doses of isosorbide mononitrate, nitric oxide has a bigger effect on larger muscular arteries over small resistance arteries. Arterial relaxation leads to reduced systemic vascular resistance and systolic blood (aortic) pressure, decreasing to decreased cardiac afterload.7,3 The direct dilator effect on coronary arteries opposes the coronary artery spasm in variant angina or angina pectoris.3 At larger doses, nitric oxide causes the resistance arteries and arterioles to dilate, reducing arterial pressure via coronary vasodilatation. This leads to increased coronary blood flow.7,3 Reduced cardiac preload and afterload caused by nitric oxide causes a reduction in myocardial oxygen consumption; decreased myocardial oxygen demand, along with increased coronary blood flow, leads to an increased in the oxygen content of coronary sinus blood 3 and the relief from ischemia.7

The end effect of isosorbide mononitrate include decreased cardiac oxygen consumption, redistribution coronary flow toward ischemic areas via collaterals, and the relief of coronary spasms. Nitric oxide can also increase the rate of relaxation of cardiac muscles, which is an effect outside of vascular smooth muscles.3 Organic nitrates can also relax other types of smooth muscles, including esophageal and biliary smooth muscle.3 The anti-anginal activity of isosorbide mononitrate was observed about 1 hour after dosing, and the peak effect was achieved from 1-4 hours after dosing.4 The duration of anti-anginal action of at least 12 hours was observed with an asymmetrical dosing regimen.2

Mechanism of action

Isosorbide mononitrate acts as a prodrug for nitric oxide (NO), which is a potent vasodilator gas that is released when the drug is metabolized. NO activates soluble guanylyl cyclase in vascular endothelial cells, which increases the intracellular concentrations of cyclic GMP (cGMP). cGMP activates cGMP-dependent protein kinases, such as protein kinase G and I, which activates the downstream intracellular cascades.1 The downstream cascade results in reduced intracellular concentrations of calcium, caused by processes including inhibition of IP3-mediated pathway, phosphorylation of big calcium-activated potassium channel leading to cell hyperpolarization and reduced calcium influx, and increased calcium efflux via the Ca2+-ATPase-pump.1 Reduced intracellular calcium concentrations lead to the dephosphorylation of myosin light chains and the relaxation of smooth muscle cells.7,3

TargetActionsOrganism
AGuanylate cyclase soluble subunit alpha-2
activator
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

Learn more
Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

Learn more
Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

Learn more
Absorption

Upon oral administration, isosorbide mononitrate is rapidly and completely absorbed from the gastrointestinal tract. Isosorbide mononitrate has a dose-linear kinetics and the absolute bioavailability is nearly 100%. The Cmax is reached within 30 to 60 minutes following administration.4

Volume of distribution

The volume of distribution is approximately 0.6 L/kg, which is approximately the volume of total body water.2,4

Protein binding

Isosorbide mononitrate is about 5% bound to plasma proteins.4

Metabolism

Isosorbide mononitrate is not subject to first pass metabolism in human liver.4 Detectable metabolites include isosorbide, sorbitol, and 2-glucuronide of mononitrate, which are pharmacologically inactive.2,4

Route of elimination

In a human radio-labelled drug study, about 93% of the total dose was excreted in the urine within 48 hours.4 Following oral administration of 20 mg, only 2% of isosorbide mononitrate was excreted unchanged in the urine within 24 hours. 2 Among the excreted dose, nearly half of the dose was found de-nitrated in urine as isosorbide and sorbitol: approximately 30% is excreted as isosorbide and about 17% is the 2-glucuronide of mononitrate.2 These metabolites were not vasoactive or pharmacologically active. Renal excretion was complete after 5 days, and fecal excretion accounted for only 1% of drug elimination.4

Half life

The elimination half-life of isosorbide mononitrate is about 5 hours.4 The elimination half-life of its metabolites, isosorbide and 2-glucuronide of mononitrate, are 8 hours and 6 hours, respectively.2

Clearance

The total body clearance is 115-120 mL/min.2

Toxicity

The oral LD50 is 2010 mg/kg in rats and 1771 mg/kg in mice.5

The symptoms of overdose from isosorbide mononitrate is associated with vasodilatation, venous pooling, reduced cardiac output, and hypotension. These symptoms can be accompanied by several manifestations, including increased intracranial pressure (possibly along with persistent throbbing headache, confusion, and moderate fever), vertigo, palpitations, visual disturbances, nausea and vomiting (possibly along with colic and bloody diarrhea), syncope (especially in the upright posture), air hunger and dyspnea (later followed by reduced ventilatory effort), diaphoresis (with flushed or cold and clammy skin), heart blocks and bradycardia, paralysis, coma, seizures, and death.4

There is limited clinical information on the management of isosorbide mononitrate overdose; it is advised that venodilatation and arterial hypovolemia from overdose are responded with therapy aimed to increase in central fluid volume. However, this method may be potentially hazardous in patients with renal disease or congestive heart failure: invasive monitoring may be required in these patients. The patient's legs should be passively elevated, and intravenous infusion of normal saline or similar fluid is recommended. Isosorbide mononitrate was shown to be significantly removed from the systemic circulation via hemodialysis. The use of epinephrine or other arterial vasoconstrictors is not recommended.4

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the orthostatic hypotensive activities of Isosorbide mononitrate.
AbacavirIsosorbide mononitrate may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Isosorbide mononitrate which could result in a higher serum level.
AcebutololThe risk or severity of adverse effects can be increased when Isosorbide mononitrate is combined with Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Isosorbide mononitrate which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Isosorbide mononitrate which could result in a higher serum level.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Isosorbide mononitrate.
AcetazolamideAcetazolamide may increase the excretion rate of Isosorbide mononitrate which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Isosorbide mononitrate which could result in a higher serum level.
AclidiniumIsosorbide mononitrate may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Take with or without food. The absorption is unaffected by food.

References

General References
  1. Munzel T, Steven S, Daiber A: Organic nitrates: update on mechanisms underlying vasodilation, tolerance and endothelial dysfunction. Vascul Pharmacol. 2014 Dec;63(3):105-13. doi: 10.1016/j.vph.2014.09.002. Epub 2014 Oct 14. [PubMed:25446162]
  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. 21. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 260-261). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  4. FDA Approved Drug Products: Monoket (isosorbide mononitrate) tablets [Link]
  5. Spectrum Chemical: 5-Isosorbide Mononitrate MSDS [Link]
  6. DailyMed Label: Isosorbide Mononitrate (ISMN) extended-release tablets [Link]
  7. Organic Nitrates - LiverTox - NCBI Bookshelf [Link]
External Links
Human Metabolome Database
HMDB0015155
KEGG Drug
D00630
KEGG Compound
C07714
PubChem Compound
27661
PubChem Substance
46506594
ChemSpider
25736
RxNav
28004
ChEBI
6062
ChEMBL
CHEMBL1311
ZINC
ZINC000001849548
Therapeutic Targets Database
DAP001058
PharmGKB
PA450126
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Isosorbide_mononitrate
ATC Codes
C01DA14 — Isosorbide mononitrate
AHFS Codes
  • 24:12.08 — Nitrates and Nitrites
FDA label
Download (217 KB)
MSDS
Download (66.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers2
1CompletedDiagnosticHigh Blood Pressure (Hypertension)1
1CompletedTreatmentBioequivalence1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1Not Yet RecruitingTreatmentAnal Fissures1
1, 2Active Not RecruitingSupportive CareInduction of Labour1
2CompletedPreventionCerebral Small Vessels Disease / Cognitive Impairments / Stroke1
2CompletedTreatmentHeart Failure / Preserved Ejection Fraction1
2RecruitingTreatmentCervical Ripening1
2RecruitingTreatmentHigh Blood Pressure (Hypertension) / Kidney Injury / Proteinuria1
2RecruitingTreatmentInduction of Labour1
2RecruitingTreatmentMissed Abortion1
2WithdrawnTreatmentHigh Blood Pressure (Hypertension)1
2, 3CompletedTreatmentIsolated (Idiopathic) Oligohydramnios1
2, 3RecruitingPreventionCerebral Small Vessels Disease / Stroke, Lacunar1
3CompletedSupportive CareInduction of Labor Affected Fetus / Newborn / Rupture of Membranes Prior to Onset of Labor1
3Not Yet RecruitingPreventionContraception1
3Not Yet RecruitingPreventionIUD Insertion Pain1
3RecruitingSupportive CareInduction of Labor Affected Fetus / Newborn1
3Unknown StatusTreatmentStable Angina (SA)1
4CompletedPreventionGastrointestinal Hemorrhage / Liver Cirrhosis / Portal Hypertension1
4CompletedPreventionVariceal Rebleeding1
4CompletedTreatmentAcute Heart Failure (AHF)1
4CompletedTreatmentSecond Trimester Abortions1
4Not Yet RecruitingTreatmentCoronary Artery Disease (CAD)2
4RecruitingTreatmentAntispastic Therapy / Coronary Artery Bypass Grafting (CABG) / Pilot Study / Radial Artery Grafts1
Not AvailableCompletedTreatmentMigraine1
Not AvailableCompletedTreatmentType 2 Diabetes Mellitus1
Not AvailableNot Yet RecruitingTreatmentIUD Insertion Complication1
Not AvailableRecruitingOtherHeadache / Healthy Volunteers2
Not AvailableRecruitingPreventionPreeclampsia / Premature Labour1
Not AvailableWithdrawnNot AvailableCoronary Heart Disease (CHD)1

Pharmacoeconomics

Manufacturers
  • Schering plough corp
  • Actavis elizabeth llc
  • Brightstone pharma inc
  • Dexcel ltd
  • Elan pharmaceutical research corp
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Kremers urban co
  • Kv pharmaceutical co
  • Vintage pharmaceuticals inc
  • West ward pharmaceutical corp
  • Promius pharma llc
  • Teva pharmaceuticals usa inc
  • Schwarz gmbh
Packagers
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Alvogen Inc.
  • Apothecon
  • A-S Medication Solutions LLC
  • AstraZeneca Inc.
  • Atlantic Biologicals Corporation
  • Bryant Ranch Prepack
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Dexcel Ltd.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Elan Pharmaceuticals Inc.
  • Ethex Corp.
  • Heartland Repack Services LLC
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Mckesson Corp.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Neuman Distributors Inc.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Promius Pharma
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Schering Corp.
  • Schwarz Pharma Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • Vangard Labs Inc.
  • West-Ward Pharmaceuticals
Dosage forms
FormRouteStrength
Tablet, extended releaseOral
TabletOral120 mg/1
TabletOral30 mg/1
TabletOral60 mg/1
Tablet, extended releaseOral60 mg
Tablet, film coatedOral20 mg/1
TabletOral
TabletOral10 mg/1
TabletOral20 mg/1
Tablet, coatedOral20 mg/1
Tablet, extended releaseOral120 mg/1
Tablet, extended releaseOral30 mg/1
Tablet, extended releaseOral60 mg/1
Tablet, film coated, extended releaseOral120 mg/1
Tablet, film coated, extended releaseOral30 mg/1
Tablet, film coated, extended releaseOral60 mg/1
Prices
Unit descriptionCostUnit
Imdur er 120 mg tablet4.19USD tablet
Imdur 120 mg 24 Hour tablet3.15USD tablet
Imdur 60 mg 24 Hour tablet3.11USD tablet
Imdur er 60 mg tablet2.99USD tablet
Imdur 30 mg 24 Hour tablet2.87USD tablet
Imdur er 30 mg tablet2.85USD tablet
Monoket 20 mg tablet2.65USD tablet
Ismo 20 mg tablet2.1USD tablet
Monoket 10 mg tablet1.75USD tablet
Isosorbide Mononitrate CR 60 mg 24 Hour tablet1.48USD tablet
Isosorbide Mononitrate CR 30 mg 24 Hour tablet1.16USD tablet
Isosorbide Mononitrate 20 mg tablet0.78USD tablet
Isosorbide Mononitrate 10 mg tablet0.74USD tablet
Imdur 60 mg Extended-Release Tablet0.74USD tablet
Isosorbide mn 20 mg tablet0.72USD tablet
Isosorbide mn 10 mg tablet0.71USD tablet
Apo-Ismn 60 mg Extended-Release Tablet0.42USD tablet
Pms-Ismn 60 mg Extended-Release Tablet0.42USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP-0.15SANGSTER (1993)
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier+0.9355
Caco-2 permeable-0.579
P-glycoprotein substrateNon-substrate0.7621
P-glycoprotein inhibitor INon-inhibitor0.7159
P-glycoprotein inhibitor IINon-inhibitor0.9116
Renal organic cation transporterNon-inhibitor0.8563
CYP450 2C9 substrateNon-substrate0.8674
CYP450 2D6 substrateNon-substrate0.8613
CYP450 3A4 substrateSubstrate0.5357
CYP450 1A2 substrateNon-inhibitor0.8532
CYP450 2C9 inhibitorNon-inhibitor0.8769
CYP450 2D6 inhibitorNon-inhibitor0.9106
CYP450 2C19 inhibitorNon-inhibitor0.8469
CYP450 3A4 inhibitorNon-inhibitor0.9471
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9596
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.7696
BiodegradationReady biodegradable0.8359
Rat acute toxicity2.0753 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5741
hERG inhibition (predictor II)Non-inhibitor0.9304
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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 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
show 1 more
Substituents
Isosorbide / Organic nitrate / Tetrahydrofuran / Alkyl nitrate / Organic nitric acid or derivatives / Secondary alcohol / Organic nitro compound / Dialkyl ether / Ether / Oxacycle
show 10 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
nitrate ester, glucitol derivative (CHEBI:6062)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
General Function
Heme binding
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
Uniprot Name
Guanylate cyclase soluble subunit alpha-2
Molecular Weight
81749.185 Da
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]
  3. Munzel T, Steven S, Daiber A: Organic nitrates: update on mechanisms underlying vasodilation, tolerance and endothelial dysfunction. Vascul Pharmacol. 2014 Dec;63(3):105-13. doi: 10.1016/j.vph.2014.09.002. Epub 2014 Oct 14. [PubMed:25446162]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTM1
Uniprot ID
P09488
Uniprot Name
Glutathione S-transferase Mu 1
Molecular Weight
25711.555 Da
References
  1. Munzel T, Steven S, Daiber A: Organic nitrates: update on mechanisms underlying vasodilation, tolerance and endothelial dysfunction. Vascul Pharmacol. 2014 Dec;63(3):105-13. doi: 10.1016/j.vph.2014.09.002. Epub 2014 Oct 14. [PubMed:25446162]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Xanthine oxidase activity
Specific Function
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Ha...
Gene Name
XDH
Uniprot ID
P47989
Uniprot Name
Xanthine dehydrogenase/oxidase
Molecular Weight
146422.99 Da
References
  1. Munzel T, Steven S, Daiber A: Organic nitrates: update on mechanisms underlying vasodilation, tolerance and endothelial dysfunction. Vascul Pharmacol. 2014 Dec;63(3):105-13. doi: 10.1016/j.vph.2014.09.002. Epub 2014 Oct 14. [PubMed:25446162]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Zinc ion binding
Specific Function
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name
ADH5
Uniprot ID
P11766
Uniprot Name
Alcohol dehydrogenase class-3
Molecular Weight
39723.945 Da
References
  1. Munzel T, Steven S, Daiber A: Organic nitrates: update on mechanisms underlying vasodilation, tolerance and endothelial dysfunction. Vascul Pharmacol. 2014 Dec;63(3):105-13. doi: 10.1016/j.vph.2014.09.002. Epub 2014 Oct 14. [PubMed:25446162]

Drug created on June 13, 2005 07:24 / Updated on July 09, 2020 11:59

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates