- Isosorbide mononitrate
- Accession Number
- DB01020 (APRD00528)
- Small Molecule
Isosorbide mononitrate is a drug used principally in the treatment of angina pectoris 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. Up to 30% of patients experience headaches and 2-3 % of patients withdraw treatment for this reason, but the incidence reduces rapidly as treatment continues . Common. 6% of patients experience tiredness, sleep disturbances, and gastrointestinal disturbances. 4-5% of patients experience hypotension, 2.5% experience poor appetite, and 1% experience nausea. Patients experience similar adverse effects as they would for all nitrate treatments and their incidence is most common early in treatment. 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
- IS 5-MN
- Isosorbide 5-mononitrate
- Isosorbide 5-nitrate
- Isosorbide mononitrate
- Isosorbidi mononitras
- Mononitrate d'isosorbide
- Mononitrato de isosorbida
- External IDs
- AHR-4698 / BM 22.145 / BM-22.145 / BM-22145
- Active Moieties
Name Kind UNII CAS InChI Key Isosorbide unknown WXR179L51S 652-67-5 KLDXJTOLSGUMSJ-JGWLITMVSA-N
- Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Imdur Tablet, extended release 60 mg Oral Mda Inc. 1994-12-31 Not applicable Imdur Tablet 120 mg/1 Oral Schering Corporation 2003-09-01 2006-11-30 Imdur Tablet 60 mg/1 Oral Schering Corporation 2003-09-01 2006-10-31 Imdur Tablet 30 mg/1 Oral Schering Corporation 2003-09-01 2006-10-31 Ismn Tablet, extended release Oral Sivem Pharmaceuticals Ulc 2015-10-08 2017-06-27 Ismo Tablet, film coated 20 mg/1 Oral Reddy Pharmaceuticals, LLC 2007-03-31 Not applicable Ismo Tab 20mg Tablet Oral Wyeth Ayerst Canada Inc. 1994-12-31 2002-06-10 Monoket Tablet 10 mg/1 Oral Ucb Inc 1993-06-30 2012-07-11 Monoket Tablet 20 mg/1 Oral Kremers Urban 1993-06-30 Not applicable Monoket Tablet 10 mg/1 Oral Kremers Urban 1993-06-30 Not applicable
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Apo-ismn Tablet, extended release Oral Apotex Corporation 2006-03-03 Not applicable Dom-ismn Tablet, extended release Oral Dominion Pharmacal Not applicable Not applicable Imdur Tablet, extended release 120 mg/1 Oral Schering Corporation 2006-01-05 2017-04-06 Imdur Tablet, extended release 30 mg/1 Oral Physicians Total Care, Inc. 2009-12-02 2012-06-30 Imdur Tablet, extended release 60 mg/1 Oral Schering Corporation 2006-01-05 2017-04-06 Imdur Tablet, extended release 30 mg/1 Oral Schering Corporation 2006-01-05 2017-04-06 Imdur Tablet, extended release 60 mg/1 Oral Physicians Total Care, Inc. 1997-01-03 2012-06-30 Isorsorbide Mononitrate Tablet, film coated, extended release 60 mg/1 Oral Actavis Pharma Company 2005-05-04 2006-07-30 Isorsorbide Mononitrate Tablet, film coated, extended release 30 mg/1 Oral Actavis Pharma Company 2005-05-04 2006-07-30 Isosorbide Tablet, film coated, extended release 30 mg/1 Oral bryant ranch prepack 2006-03-30 Not applicable
- 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
- Antianginal Agents
- Cardiac Therapy
- Cardiovascular Agents
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 Substrates
- Delayed-Action Preparations
- Drugs that are Mainly Renally Excreted
- Hypotensive Agents
- Methemoglobinemia Associated Agents
- Nitrate Vasodilator
- Nitrates and Nitrites
- Nitric Oxide Donors
- Organic Nitrates
- Sugar Alcohols
- Vasodilating Agents
- Vasodilators Used in Cardiac Diseases
- CAS number
- Average: 191.1388
- Chemical Formula
- InChI Key
- IUPAC Name
- (3R,3aS,6S,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl nitrate
For the prevention of angina pectoris due to coronary artery disease and the treatment of acute and chronic angina pectoris, hypertension, and myocardial infarction.
- Associated Conditions
Isosorbide-5-mononitrate, the long-acting metabolite of isosorbide dinitrate, is used as a vasodilatory agent in the management of angina pectoris. By dilating the vessels, it lowers the blood pressure and reduces the left ventricular preload and afterload, therefore, leads to a reduction of myocardial oxygen requirement.
- Mechanism of action
Similar to other nitrites and organic nitrates, Isosorbide Mononitrate 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.
Target Actions Organism AGuanylate cyclase soluble subunit alpha-2inducer Humans
- Volume of distribution
- 0.6 to 0.7 L/kg
- Protein binding
- Route of elimination
Isosorbide mononitrate is primarily metabolized by the liver, but unlike oral isosorbide dinitrate, it is not subject to first-pass metabolism. Isosorbide mononitrate is cleared by denitration to isosorbide and glucuronidation as the mononitrate, with 96% of the administered dose excreted in the urine within 5 days and only about 1% eliminated in the feces. At least six different compounds have been detected in urine, with about 2% of the dose excreted as the unchanged drug and at least five metabolites.
- Half life
- 120–122 mL/min [Single dose of 60 mg PO]
- 151–187 mL/min [Single dose of extended-release tablet 60 mg PO]
- 132-151 mL/min [Multiple doses of extended release tablet 60 mg PO]
- 119-140 mL/min [Multiple doses of extended release tablet 120 mg PO]
Symptoms of overdose include vasodilatation, venous pooling, reduced cardiac output, and hypotension. There are no data suggesting what dose of isosorbide mononitrate is likely to be life-threatening in humans. In rats and mice, there is significant lethality at doses of 2000 mg/kg and 3000 mg/kg, respectively.
- Affected organisms
- Humans and other mammals
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
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
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
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- 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.
Drug Interaction 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the orthostatic hypotensive activities of Isosorbide Mononitrate. Abacavir Isosorbide mononitrate may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose Acarbose may decrease the excretion rate of Isosorbide mononitrate which could result in a higher serum level. Acebutolol The therapeutic efficacy of Acebutolol can be increased when used in combination with Isosorbide mononitrate. Aceclofenac Aceclofenac may decrease the excretion rate of Isosorbide mononitrate which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Isosorbide mononitrate which could result in a higher serum level. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Isosorbide mononitrate. Acetazolamide Acetazolamide may increase the excretion rate of Isosorbide mononitrate which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Isosorbide mononitrate which could result in a higher serum level. Aclidinium Isosorbide mononitrate may decrease the excretion rate of Aclidinium which could result in a higher serum level.Additional Data Available
- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.Learn more
A severity rating for each drug interaction, from minor to major.Learn more
- Evidence LevelEvidence Level
A rating for the strength of the evidence supporting each drug interaction.Learn more
An effect category for each drug interaction. Know how this interaction affects the subject drug.Learn more
- Food Interactions
- Take without regard to meals.
- General References
- Not Available
- External Links
- ATC Codes
- C01DA14 — Isosorbide mononitrate
- AHFS Codes
- 24:12.08 — Nitrates and Nitrites
- FDA label
- Download (217 KB)
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- Clinical Trials
- 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
- Actavis Group
- Advanced Pharmaceutical Services Inc.
- Alvogen Inc.
- 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
Form Route Strength Tablet, extended release Oral Tablet Oral 120 mg/1 Tablet Oral 30 mg/1 Tablet Oral 60 mg/1 Tablet, extended release Oral 60 mg Tablet, film coated Oral 20 mg/1 Tablet Oral Tablet Oral 10 mg/1 Tablet Oral 20 mg/1 Tablet, coated Oral 20 mg/1 Tablet, extended release Oral 120 mg/1 Tablet, extended release Oral 30 mg/1 Tablet, extended release Oral 60 mg/1 Tablet, film coated, extended release Oral 120 mg/1 Tablet, film coated, extended release Oral 30 mg/1 Tablet, film coated, extended release Oral 60 mg/1
Unit description Cost Unit Imdur er 120 mg tablet 4.19USD tablet Imdur 120 mg 24 Hour tablet 3.15USD tablet Imdur 60 mg 24 Hour tablet 3.11USD tablet Imdur er 60 mg tablet 2.99USD tablet Imdur 30 mg 24 Hour tablet 2.87USD tablet Imdur er 30 mg tablet 2.85USD tablet Monoket 20 mg tablet 2.65USD tablet Ismo 20 mg tablet 2.1USD tablet Monoket 10 mg tablet 1.75USD tablet Isosorbide Mononitrate CR 60 mg 24 Hour tablet 1.48USD tablet Isosorbide Mononitrate CR 30 mg 24 Hour tablet 1.16USD tablet Isosorbide Mononitrate 20 mg tablet 0.78USD tablet Isosorbide Mononitrate 10 mg tablet 0.74USD tablet Imdur 60 mg Extended-Release Tablet 0.74USD tablet Isosorbide mn 20 mg tablet 0.72USD tablet Isosorbide mn 10 mg tablet 0.71USD tablet Apo-Ismn 60 mg Extended-Release Tablet 0.42USD tablet Pms-Ismn 60 mg Extended-Release Tablet 0.42USD tabletDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
- Not Available
- Experimental Properties
Property Value Source melting point (°C) 88-91 °C Not Available water solubility 1.07E+005 mg/L Not Available logP -0.15 SANGSTER (1993)
- Predicted Properties
Property Value Source Water Solubility 57.0 mg/mL ALOGPS logP -0.74 ALOGPS logP -0.48 ChemAxon logS -0.53 ALOGPS pKa (Strongest Acidic) 13.34 ChemAxon pKa (Strongest Basic) -3.5 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 93.74 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 38.08 m3·mol-1 ChemAxon Polarizability 15.85 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon
- Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9156 Blood Brain Barrier + 0.9355 Caco-2 permeable - 0.579 P-glycoprotein substrate Non-substrate 0.7621 P-glycoprotein inhibitor I Non-inhibitor 0.7159 P-glycoprotein inhibitor II Non-inhibitor 0.9116 Renal organic cation transporter Non-inhibitor 0.8563 CYP450 2C9 substrate Non-substrate 0.8674 CYP450 2D6 substrate Non-substrate 0.8613 CYP450 3A4 substrate Substrate 0.5357 CYP450 1A2 substrate Non-inhibitor 0.8532 CYP450 2C9 inhibitor Non-inhibitor 0.8769 CYP450 2D6 inhibitor Non-inhibitor 0.9106 CYP450 2C19 inhibitor Non-inhibitor 0.8469 CYP450 3A4 inhibitor Non-inhibitor 0.9471 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9596 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.7696 Biodegradation Ready biodegradable 0.8359 Rat acute toxicity 2.0753 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5741 hERG inhibition (predictor II) Non-inhibitor 0.9304
- Mass Spec (NIST)
- Not Available
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
- 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.
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Sub Class
- Direct Parent
- 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 compoundsHydrocarbon derivatives show 1 more
- Isosorbide / Organic nitrate / Tetrahydrofuran / Alkyl nitrate / Organic nitric acid or derivatives / Secondary alcohol / Organic nitro compound / Dialkyl ether / Ether / OxacycleAllyl-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 show 10 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- nitrate ester, glucitol derivative (CHEBI:6062)
- Pharmacological action
- 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
- Uniprot ID
- Uniprot Name
- Guanylate cyclase soluble subunit alpha-2
- Molecular Weight
- 81749.185 Da
- Moncada S, Palmer RM, Higgs EA: Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol Rev. 1991 Jun;43(2):109-42. [PubMed:1852778]
- 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]
Drug created on June 13, 2005 07:24 / Updated on November 20, 2019 12:23