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Isosorbide mononitrate

Isosorbide mononitrate is an organic nitrate medication primarily used to prevent and treat angina pectoris due to coronary artery disease.^[1] It belongs to the class of nitrate vasodilators and functions by releasing nitric oxide, which activates guanylate cyclase in vascular smooth muscle cells, increasing cyclic guanosine monophosphate (cGMP) levels and leading to vasodilation.^[1] This action primarily dilates venous capacitance vessels, reducing preload on the heart and improving myocardial oxygen supply, while also modestly dilating coronary arteries to enhance blood flow to ischemic areas.^[1] Unlike isosorbide dinitrate, its active metabolite, isosorbide mononitrate has nearly 100% bioavailability due to the absence of a first-pass effect in the liver, allowing for reliable oral administration.^[2] The drug is available in immediate-release tablets (typically 5–20 mg) and extended-release formulations (30–120 mg), with dosing regimens designed to include a nitrate-free interval—often 10–12 hours daily—to prevent tolerance development.^[1] Standard immediate-release dosing starts at 20 mg twice daily, spaced about 7 hours apart,^[3] while extended-release is taken once daily;^[1] no adjustments are required for renal or hepatic impairment.^[3] Beyond its primary indication for chronic stable angina, isosorbide mononitrate may be used adjunctively with beta-blockers for secondary prophylaxis of recurrent variceal hemorrhage in patients with portal hypertension.^[1] It is not intended for the immediate relief of acute anginal attacks, where sublingual nitroglycerin is preferred.^[3] Chemically, isosorbide mononitrate (C₆H₉NO₆, molecular weight 191.14 g/mol) is a mononitrate ester of the sugar alcohol isosorbide, appearing as a crystalline solid with a half-life of approximately 5 hours.^[2] Common brand names include Imdur, Ismo, and Monoket.^[2] Adverse effects are dose-related and include headache (affecting up to 35% of patients), dizziness, hypotension, reflex tachycardia, and nausea; severe reactions like methemoglobinemia are rare.^[1]^[3] Contraindications encompass hypersensitivity to nitrates, concurrent use with phosphodiesterase-5 inhibitors (e.g., sildenafil) or riociguat due to risk of profound hypotension, and conditions like hypertrophic cardiomyopathy or right ventricular infarction.^[1] Overall, its profile supports long-term use in angina management when monitored appropriately to balance efficacy and tolerance risks.^[1]

Chemistry

Chemical structure and properties

Isosorbide mononitrate is classified as an organic nitrate ester, serving as the major active metabolite of isosorbide dinitrate, which features two nitrate groups at the 2- and 5-positions of the bicyclic ring system.^[4] Unlike its parent compound, isosorbide mononitrate contains a single nitrate group, contributing to its chemical stability and pharmacokinetic profile.^[2] The molecular formula of isosorbide mononitrate is C₆H₉NO₆, with a molecular weight of 191.14 g/mol.^[2] Its chemical structure is a bicyclic derivative of sorbitol, specifically 1,4:3,6-dianhydro-D-glucitol 5-nitrate, featuring a nitrate ester group attached at the 5-position of the 1,4:3,6-dianhydrohexitol ring.^[4] This rigid bicyclic framework enhances its lipophilicity compared to linear nitrates, influencing its absorption and distribution characteristics.^[2] Physically, isosorbide mononitrate appears as a white, odorless crystalline powder.^[5] It is freely soluble in water, with a reported solubility of approximately 57 g/L at 25°C, and also dissolves readily in organic solvents such as ethanol, methanol, and chloroform.^[2] The compound has a melting point in the range of 88–93°C, indicating moderate thermal stability suitable for pharmaceutical formulations.^[2]

Synthesis and metabolism

Isosorbide mononitrate is primarily obtained as the major active metabolite of isosorbide dinitrate through hepatic denitration during first-pass metabolism of the dinitrate precursor.^[1] Direct chemical synthesis involves regioselective nitration of isosorbide, typically at the 5-position, using nitrating mixtures such as nitric acid with acetic anhydride or fuming nitric acid in acetic acid, followed by purification to isolate the 5-mononitrate isomer.^[6] Industrial processes often employ selective de-nitration of isosorbide dinitrate via mild hydrolysis or reduction to yield high-purity isosorbide-5-mononitrate, minimizing formation of the less active 2-mononitrate isomer.^[7] In the body, isosorbide mononitrate undergoes hepatic metabolism primarily through denitration and glucuronidation, producing inactive metabolites such as isosorbide, the 5-mononitrate glucuronide, and the 2-glucuronide derivative.^[1] Unlike isosorbide dinitrate, it experiences negligible first-pass hepatic extraction, resulting in nearly complete bioavailability of approximately 100% after oral administration.^[8] The elimination half-life is about 5 hours, with clearance occurring at a rate of approximately 115 mL/min and a volume of distribution of 0.6 L/kg.^[8] Excretion occurs mainly via the kidneys, with less than 2% of the dose eliminated as unchanged drug and the remainder as glucuronidated metabolites.^[1]

Pharmacology

Mechanism of action

Isosorbide mononitrate acts as a prodrug that undergoes metabolic activation to release nitric oxide (NO) intracellularly within vascular smooth muscle cells. This NO then diffuses to activate soluble guanylate cyclase, leading to an increase in cyclic guanosine monophosphate (cGMP) levels.^[1]^[9] Elevated cGMP activates cGMP-dependent protein kinases, which in turn promote the dephosphorylation of myosin light chains through activation of myosin light chain phosphatase and inhibition of myosin light chain kinase via reduced intracellular calcium concentrations. This process results in relaxation of vascular smooth muscle, causing vasodilation primarily in venous capacitance vessels, with lesser effects on arterioles and coronary arteries.^[1]^[9]^[10] The predominant venodilation decreases venous return to the heart, thereby reducing preload and myocardial oxygen demand, while the milder arterial dilation lowers systemic vascular resistance and afterload to further alleviate cardiac workload.^[1]^[9]^[11] As a long-acting organic nitrate, isosorbide mononitrate is formulated for once-daily dosing with a nitrate-free interval, which minimizes the development of tolerance compared to shorter-acting nitrates like nitroglycerin that require more frequent administration and are prone to rapid tolerance without such intervals.^[12]^[13]^[14]

Pharmacokinetics

Isosorbide mononitrate is rapidly and completely absorbed from the gastrointestinal tract following oral administration, with an absolute bioavailability approaching 100% due to the absence of significant first-pass metabolism.^[15] For immediate-release formulations, peak plasma concentrations are typically achieved within 0.5 to 1 hour after dosing, while extended-release formulations exhibit a delayed time to peak of approximately 3 to 4 hours, allowing for once-daily administration.^[15]^[16] Absorption is not significantly affected by food, and pharmacokinetics demonstrate dose proportionality across the therapeutic range of 30 to 240 mg.^[15] The drug is widely distributed throughout the body, with a volume of distribution of approximately 0.6 to 0.7 L/kg, roughly equivalent to total body water.^[9] Plasma protein binding is minimal, at less than 5%, facilitating its availability for pharmacological action.^[9] Metabolism occurs primarily in the liver through denitration, reducing isosorbide mononitrate to inactive metabolites such as isosorbide and sorbitol, with no involvement of the cytochrome P450 system.^[15] About half of the dose is metabolized to these non-vasoactive compounds, and another quarter is conjugated to glucuronides of the parent drug, all of which are pharmacologically inert.^[15] Elimination is predominantly renal, with over 93% of the administered dose excreted in the urine within 48 hours, primarily as metabolites, and virtually complete after five days; fecal excretion accounts for only about 1%.^[15] The elimination half-life is approximately 5 hours, and systemic clearance is around 100 to 120 mL/min, remaining consistent across healthy individuals, the elderly, and those with renal, hepatic, or cardiac impairment.^[8] No dosage adjustments are typically required in these populations, though the drug is significantly removed by hemodialysis.^[15]

Medical uses

Indications

Isosorbide mononitrate is primarily indicated for the prevention of angina pectoris in patients with chronic stable angina due to coronary artery disease.^[15]^[1] It works by dilating blood vessels to improve blood flow to the heart, thereby reducing the frequency and severity of angina episodes, but it is not suitable for the immediate relief of acute anginal attacks due to its slower onset of action.^[17] Clinical trials and meta-analyses have demonstrated its efficacy in this role, with significant improvements in exercise tolerance and a reduction in weekly angina attacks by approximately 1.5 to 2.9 episodes compared to placebo in patients with stable effort angina.^[18]^[19] It is not recommended as monotherapy for acute coronary syndromes, where faster-acting nitrates are preferred.^[1] The medication is typically selected for patients with chronic stable angina who require long-term prophylaxis, often in combination with beta-blockers or calcium channel blockers to enhance anti-ischemic effects and optimize symptom control.^[20] This approach is supported by guidelines emphasizing its role in multidrug regimens for better outcomes in coronary artery disease management.^[20] Secondary uses include its application as an adjunct therapy in heart failure to reduce preload through venodilation, although evidence from randomized trials indicates mixed results, with some showing no improvement in exercise capacity or quality of life and potential reductions in daily activity levels.^[1]^[21] It is also used adjunctively with non-selective beta-blockers for secondary prophylaxis of recurrent variceal bleeding in patients with cirrhosis and portal hypertension, as supported by randomized trials showing reduced rebleeding risk.^[1]^[22] Additionally, isosorbide mononitrate is used off-label in some regions for the treatment of diffuse esophageal spasms, where it helps relieve pain and dysphagia by relaxing esophageal smooth muscle, as evidenced by small clinical studies on nitrates demonstrating symptom improvement.^[1]^[23]

Dosage and administration

Isosorbide mononitrate is available in immediate-release (IR) oral tablets in strengths ranging from 5 mg to 40 mg and extended-release (ER) oral tablets in strengths of 30 mg, 60 mg, and 120 mg.^[24] For IR formulations, the recommended initial dose is 20 mg administered orally twice daily, with doses taken approximately 7 hours apart to provide a nitrate-free interval and reduce the risk of tolerance. Doses may be titrated based on clinical response, typically ranging from 10 mg to 40 mg per dose, with the first dose taken upon awakening.^[15]^[24] For ER formulations, the starting dose is 30 mg or 60 mg once daily in the morning, which may be increased to 120 mg once daily after several days if necessary for efficacy; the maximum dose is 240 mg once daily, though doses exceeding 120 mg are seldom required.^[25]^[26] Tablets are taken orally with or without food, and ER tablets must be swallowed whole without splitting, crushing, or chewing to preserve the extended-release properties. The dosing regimen for both formulations incorporates a nitrate-free interval—7 hours for IR and 12–14 hours for ER—to maintain therapeutic effectiveness and prevent tolerance.^[15]^[26] Isosorbide mononitrate is not approved for intravenous administration.^[17] In elderly patients or those with hepatic impairment, initiate therapy at the lower end of the dosing range due to potentially decreased drug clearance and increased sensitivity. No specific dose adjustments are required for mild to moderate renal impairment, but caution is advised in severe cases.^[24]^[17]

Safety and tolerability

Adverse effects

The most common adverse effect of isosorbide mononitrate is headache, which occurs in up to 57% of patients and is often dose-related, transient, and indicative of the drug's vasodilatory action.^[27]^[28] Dizziness affects approximately 4-11% of users, while flushing and hypotension are reported in 0.1-10% of cases, typically resolving with continued use or dose adjustment.^[1]^[29] Serious adverse effects include orthostatic hypotension and reflex tachycardia, each occurring in 0.1-10% of patients, which may lead to syncope or lightheadedness, particularly upon standing.^[1] Methemoglobinemia is a rare but serious complication, primarily at high doses, and can be clinically significant in patients with coronary ischemia or anemia.^[1] Gastrointestinal upset, such as nausea and diarrhea, is common (1-10%) but usually mild.^[28] With long-term continuous use, nitrate tolerance may develop within 12-24 hours, reducing the drug's efficacy and necessitating drug-free intervals of 10-12 hours daily to maintain therapeutic benefits.^[1] Monitoring involves regular blood pressure assessments to detect hypotension, especially in elderly or volume-depleted patients, and management of headaches with analgesics without altering the dose.^[1]^[29]

Contraindications and precautions

Isosorbide mononitrate is contraindicated in patients with known hypersensitivity to nitrates or nitrites, as allergic reactions can occur.^[25] Concomitant use with phosphodiesterase-5 (PDE5) inhibitors, such as sildenafil, or soluble guanylate cyclase stimulators like riociguat is absolutely contraindicated due to the risk of profound hypotension, potentially leading to syncope or myocardial ischemia.^[25] Relative contraindications include severe anemia, as the drug's oxygen-carrying capacity reduction may worsen tissue hypoxia.^[1] Caution is advised in patients with hypertrophic cardiomyopathy or conditions that increase intracranial pressure, since isosorbide mononitrate may aggravate these states through vasodilation.^[30] Caution is also advised in patients with severe hypotension or cardiogenic shock, where the vasodilatory effects could exacerbate hemodynamic instability.^[30] In patients with renal or hepatic impairment, no dosage adjustment is typically required, but close monitoring is recommended due to potential alterations in drug clearance.^[25] Precautions include avoiding abrupt discontinuation of therapy, as this can precipitate rebound angina or, in rare cases, sudden death, particularly in those with prolonged exposure; a nitrate-free interval of 10-12 hours daily helps mitigate tolerance and withdrawal risks.^[25] Concurrent use with alcohol should be minimized, as it can potentiate orthostatic hypotension and increase the likelihood of dizziness or syncope.^[31] Regarding pregnancy, isosorbide mononitrate is classified as FDA Pregnancy Category B, with animal studies showing no fetal risk but limited human data available; it should be used only if clearly needed, weighing potential benefits against risks.^[32] In cases of overdose, management is primarily supportive, focusing on maintaining blood pressure through leg elevation and intravenous fluid administration for hypotension.^[25] Methylene blue, administered intravenously at 1-2 mg/kg, is indicated for treating methemoglobinemia if it develops, while hemodialysis is ineffective for removal of the drug or its metabolites.^[30]

Interactions

Drug interactions

Isosorbide mononitrate, a nitrate vasodilator, exhibits significant drug interactions primarily through additive effects on vasodilation and hypotension. The most critical interactions occur with phosphodiesterase type 5 (PDE5) inhibitors, such as sildenafil, tadalafil, and vardenafil, and with riociguat, which potentiate the hypotensive effects by increasing cyclic guanosine monophosphate (cGMP) levels, potentially leading to profound hypotension, syncope, or myocardial ischemia.^[3]^[1] Co-administration is contraindicated, and these agents should not be used within 24 hours (48 hours for tadalafil) of isosorbide mononitrate dosing to prevent severe cardiovascular compromise.^[3]^[33] Moderate interactions arise with other vasodilators, antihypertensives, beta-blockers, and calcium channel blockers, which can enhance the hypotensive response due to synergistic vasodilation. For instance, calcium channel blockers may cause marked orthostatic hypotension, necessitating dose adjustments or careful monitoring of blood pressure.^[3] Beta-blockers like metoprolol do not significantly alter the pharmacokinetics of isosorbide mononitrate but may contribute to additive blood pressure lowering effects.^[34] Similarly, other antihypertensives increase the risk of excessive hypotension, particularly in volume-depleted patients.^[1] Isosorbide mononitrate has no clinically significant interactions with cytochrome P450 (CYP450) enzymes, as it is not metabolized via these pathways.^[9] Aspirin, commonly used for antiplatelet effects, can relieve isosorbide mononitrate-induced headaches without diminishing its antianginal efficacy.^[35] Management of these interactions involves avoiding contraindicated combinations, implementing dose reductions or timing separations for moderate interactions, and monitoring for signs of additive vasodilation such as dizziness or orthostatic hypotension.^[3]^[1]

Other interactions

Isosorbide mononitrate exhibits no significant interactions with food, and it may be administered with or without meals since food does not affect its absorption or bioavailability.^[3] Alcohol potentiates the vasodilatory effects of isosorbide mononitrate, leading to enhanced hypotension, dizziness, and lightheadedness; patients are advised to limit or avoid alcohol consumption.^[3]^[31] In disease states such as dehydration or volume depletion (hypovolemia), isosorbide mononitrate should be used with caution, as these conditions may exacerbate hypotensive effects.^[3]^[31] Lifestyle factors can influence the risk of orthostatic hypotension associated with isosorbide mononitrate; patients should avoid prolonged standing, hot environments, and sudden changes in posture, such as rising quickly from a seated or recumbent position, to minimize symptoms like dizziness or fainting.^[31]^[3]

History and society

Development and approval

Isosorbide mononitrate originated as the major biologically active metabolite of isosorbide dinitrate, an organic nitrate first synthesized in 1940. It was patented in 1971 and came into medical use in 1981. The mononitrate was identified as forming in vivo following oral administration of the dinitrate in 1967, and during the 1970s, research highlighted its pharmacokinetic advantages, including a longer duration of action and complete bioavailability without first-pass metabolism, prompting its development as a standalone therapeutic agent. This recognition stemmed from studies showing the metabolite's sustained vasodilatory effects compared to the parent compound.^[36]^[37]^[9] Clinical trials in the 1980s established the anti-anginal efficacy of isosorbide mononitrate through immediate-release formulations. A large-scale, open multicenter trial published in 1980 evaluated its use in patients with stable angina, demonstrating significant reductions in exercise-induced ischemia and good overall tolerance across diverse populations. Subsequent double-blind studies in the mid-1980s, including one involving 18 patients with stable angina, confirmed both acute hemodynamic benefits—such as improved exercise tolerance and reduced ST-segment depression—and sustained effects over two weeks of twice-daily dosing at 40 mg. Pivotal trials for the extended-release formulation, conducted in the late 1980s, focused on once-daily administration and showed prolonged anti-ischemic activity lasting up to 12 hours, with minimal tolerance development when dosed intermittently. These studies provided the foundational evidence for regulatory submissions by emphasizing the drug's role in preventing angina attacks without the need for multiple daily doses.^[38]^[39]^[39] Regulatory milestones began with initial approvals in Europe in 1980 for the prophylaxis of angina pectoris due to coronary artery disease. The U.S. Food and Drug Administration granted approval in January 1991 specifically for the extended-release formulation (marketed as Imdur), targeting angina prevention and highlighting its once-daily regimen to enhance patient compliance and reduce nitrate tolerance risks associated with continuous exposure. A key milestone was the introduction of the extended-release form (Imdur) in Europe in 1985 and in the United States in 1991, which addressed limitations of immediate-release versions by providing steady plasma levels over 24 hours, thereby improving therapeutic reliability in chronic management.^[40]^[9]^[41]

Brand names and availability

Isosorbide mononitrate is marketed under several brand names in the United States, including Imdur (extended-release), Monoket (immediate-release), and Ismo (immediate-release).^[42]^[9] Internationally, it is available as Mono Mack (immediate-release tablets) in regions such as the Middle East, and under other names like Imdur in Canada and various European countries.^[43]^[44] The drug is formulated primarily as oral tablets in both immediate-release and extended-release versions, with common strengths including 5 mg, 10 mg, 20 mg for immediate-release and 30 mg, 60 mg, 120 mg for extended-release.^[45]^[46] Generic versions have been available since the mid-1990s following the approval of initial brand formulations like Ismo in 1992 and Monoket in 1993, with extended-release generics approved later as patents expired.^[47]^[48] Isosorbide mononitrate is available by prescription only in most countries worldwide, reflecting its classification as a controlled medication for cardiovascular use.^[17]^[49] It is accessible in numerous countries through retail and hospital pharmacies, with trade data indicating exports and imports spanning over 200 nations, though approved dosages may vary by region (e.g., up to 120 mg extended-release in the US versus lower strengths in some Asian markets).^[50]^[51] As a low-cost generic, isosorbide mononitrate offers broad access, with prices as low as $0.18–$0.47 per tablet in international markets and similar affordability in the US through discount programs, making it suitable for long-term therapy in resource-limited settings.^[51]^[52]

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Generic imdur (isosorbide mononitrate er) 120 mg discount prices at U.S. pharmacies start at $0.46 per tab er 24h for 30 tab er 24hs. Enter your ZIP Code to ...