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QuickView for Isosorbide Mononitrate (compound)

Summary
General Info

PubChem

PubChem Compound 27661

PubChem Compound 27661

Name:	isosorbide-5-mononitrate
PubChem Compound ID:	27661
Molecular formula:	C₆H₉NO₆
Molecular weight:	191.139 g/mol
Synonyms:	Isosorbide 5-nitrate; Fem-Mono; IHD; Ismo (TN); Elantan; Imdur; Corangin; ISMN Stada; 5-Ismn; Monocord 20. show more » Isosorbide 5-nitrate; Fem-Mono; IHD; Ismo (TN); Elantan; Imdur; Corangin; ISMN Stada; 5-Ismn; Monocord 20; Mononit Retard 50; Monolong 60; Multitab; Nitex; Monizid; Monosordil; Monotrate; Mono Corax; Nitramin; Vasdilat; vasotrate; Titarane; Ismo-20; CCRIS 1911; Monoclair; BRN 5851319; Medocor; Iturol; Corangin SR; Pertil; Edistol; UN3251; Isosorbide Mononitrate; Isosorbide mononitrate (JAN/USAN); Olicardin; Isopen-20; Monocord 40; Monolong 40; Ismo; Olicard; Conpin; Monisid; Sorbimon; Mononit 20; Epicordin; Monis; ISMN; Monolong; Mono Mack; Isosorbidi mononitras [Latin]; ISMN AbZ; Plodin; Monicor; Monosorbitrate; 16051-77-7; Glucitol, 1,4:3,6-dianhydro-, 5-nitrate, D-; Duride; ISMN AL; D00630; Mono-Mack; IS 5MN; ISMN Hexal; BM 22-145; Elantan Long; Etimonis; Furo(3,2-b)furan, D-glucitol deriv.; Monoket; Isomon; ISMN Atid; AHR 4698; 1,4:3,6-Dianhydro-D-glucitol 5-nitrate; Monit 20; Monodur Durules; Mononit 40; Monocord 50 SR; Monoket OD; Imtrate; Isosorbide mononitrate [USAN:BAN:INN:JAN]; MonoSigma; ISMN Basics; Isomonit; Imodur; EINECS 240-197-2; Ismox; Isosorbide-5-mononitrate; Promocard; Isomonat; D-Glucitol, 1,4:3,6-dianhydro-, 5-nitrate; Uniket; Orasorbil; C07714; Monoket Retard; ZINC01849548; Pentacard 20; Imdur Durules; Percorina; Sigacora; ISMN Heumann; Isosobide-5-mononitrate [UN3251] [Flammable solid]; Elantan Retard; Mononitrato de isosorbida [Spanish]; ISMN Apogepha; Isosorbide 5-mononitrate; Turimonit; Imazin; Mononit; Mono-Sanorania; ISMN Lannacher; Mononitrate d'isosorbide [French]; Ismexin; Mono Corax Retard; Conpin Retardkaps; Imdur 60; Monopront show less «

DrugBank

Identification

Name:	isosorbide-5-mononitrate
Name (isomeric):	DB01020
Drug Type:	small molecule
Synonyms:	Monosorbitrate; IHD; Isosorbidi Mononitras [Latin]; ISMN; Mononitrate d'Isosorbide [French]; Mononitrato de Isosorbida [Spanish]
Brand:	Edistol, Monoclair, Elantan Retard, Olicard, Monocord 20, Sigacora, Duride, Ismox, Monicor, Monoket Retard, Ismexin, Monisid, Pentacard, Monolong 60, IS 5MN, Conpin, Elantan, Isomon, Ismn Abz, Monizid, Nitex, Mononit 40, Ismn Basics, Monit 20, Monotrate, Mono-Mack, Isopen-20, Nitramin, Vasdilat, Mononit Retard 50, Conpin Retardkaps, Etimonis, Ismn Heumann, Medocor, Iturol, Pentacard 20, Ismn Hexal, Ismo-20, Epicordin, Corangin Sr, Mono Corax Retard, Imodur, Uniket, Isomonit, Plodin, Isomonat, Olicardin, Multitab, Monodur Durules, Imdur 60, Pertil, Monopront, Orasorbil, Imazin, Monocord 40, ISMN AL, Mono-Sanorania, Ismn Stada, Promocard, Turimonit, Ismn Apogepha, Monis, Monit, Monolong 40, Ismn Atid, Imtrate, Monoket, Imdur, Monosordil, Mononit 20, Monosorb, Elantan Long, Sorbimon, Monocedocard, Mono Corax, Imdur Durules, Mono Mack, Monocord 50 Sr, Monoket Od, Ismn Lannacher, Vasotrate, Monolong, Corangin, Fem-Mono, Ismo, Monosigma, Mononit, Percorina, Titarane
Category:	Nitrates and Nitrites, Vasodilator Agents, Nitric Oxide Donors
CAS number:	16051-77-7

Pharmacology

Indication:	For the prevention of angina pectoris due to coronary artery disease and the treatment of acute and chronic angina pectoris, hypertension, and myocardial infarction.
Pharmacology:	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-d... show more » 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. show less «
Absorption:	100%
Protein binding:	5%
Biotransformation:	Hepatic
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:	5 hours
Clearance:	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]
Toxicity:	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

Interactions

Food interaction:

Take without regard to meals.

Drug interaction:

Telithromycin	Telithromycin may reduce clearance of Isosorbide Mononitrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Isosorbide Mononitrate if Telithromycin is initiated, discontinued or dose changed.
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of isosorbide mononitrate by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of isosorbide mononitrate if voriconazole is initiated, discontinued or dose changed.
Tadalafil	The vasodilatory effects of Isosobide mononitrate may be increased by Tadalafil. Severe hypotension may occur. Concomitant therapy is contraindicated.
Sildenafil	Possible significant hypotension with this combination
Udenafil	The vasodilatory effects of Isosobide mononitrate may be increased by Udenafil. Severe hypotension may occur. Concomitant therapy is contraindicated.

Targets

Guanylate cyclase soluble subunit alpha-2

Enzymes

Cytochrome P450 3A4