Isosorbide dinitrate

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Isosorbide dinitrate
Systematic (IUPAC) name
(3R,3aS,6S,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl dinitrate
Identifiers
CAS number	87-33-2
ATC code	C01DA08 D03AX08
PubChem	3780
DrugBank	APRD00455
Chemical data
Formula	C6H8N2O8
Mol. mass	236.136 g/mol
Pharmacokinetic data
Bioavailability	10–90%, average 25%
Metabolism	Hepatic
Half life	1 hour
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	C(US)
Legal status	℞ Prescription only
Routes	Oral

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Overview

Isosorbide dinitrate (ISDN) is a nitrate used pharmacologically as a vasodilator, e.g. in angina pectoris but also for anal fissure, a condition which is known to involve decreased blood supply leading to poor healing. It is also used as a direct vasodilator to treat congestive heart failure.

Isosorbide dinitrate is sold under the brand names Isordil®^[1] by Biovail, Cedocard® and Sorbitrate®. It is also a component of BiDil.

Uses

It is more useful in preventing angina attacks than reversing them once they have commenced. It may be given as a tablet for the treatment of an angina attack.

Advantages

Long acting nitrates can be more useful as they are generally more effective and stable in the short term.

Disadvantages

After long term use for treating chronic conditions, tolerance may develop in a patient reducing its effectiveness. The mechanisms of nitrate tolerance have been thoroughly investigated in the last 30 years and several hypotheses have been proposed. these include:

1. Impaired biotransformation of ISDN to its active pinciple NO (or a NO-related species)
2. Neurohormonal activation, causing sympathetic activation and release of vasoconstrictors such as endothelin and angiotensin II which counteract the vasodilation induced by ISDN
3. Plasma volume expansion
4. The oxidative stress hypothesis (proposed by Munzel et al in 1995).

Recent evidence suggests that the latter hypothesis might represent a unifying hypothesis, and an ISDN-induced inappropriate production of oxygen free radicals might induce a number of abnormalities which include the ones described above. Furthermore, studies have shown that nitrate tolerance is associated with vascular abnormalities which have the potential to worsen patients prognosis (Nakamura et al): these include endothelial and autonomic dysfunction (Gori et al). In the short run, ISDN can cause severe headaches, necessitating analgesic (very rarely up to morphine) administration for relief of pain as well as severe hypotension, and, in certain cases, bradycardia. This makes some physicians nervous and should prompt caution when starting nitrate administration.

Notes

v • d • e Vasodilators used in cardiac diseases (C01D)
Nitrates	Glyceryl trinitrate • Isosorbide dinitrate • Isosorbide mononitrate • Molsidomine • Pentaerythritol tetranitrate
Quinolone vasodilators	Flosequinan
Others	Itramin tosilate • Prenylamine • Oxyfedrine • Benziodarone • Carbocromen • Hexobendine • Etafenone • Heptaminol • Imolamine • Dilazep • Trapidil • Molsidomine • Efloxate • Cinepazet • Cloridarol • Nicorandil • Linsidomine • Nesiritide

v • d • e Preparations for treatment of wounds and ulcers (D03)
Cicatrizants	Cadexomer iodine - Dextranomer - Dexpanthenol - Calcium pantothenate - Hyaluronic acid - Becaplermin - Glyceryl trinitrate - Isosorbide dinitrate - Crilanomer - Enoxolone
Proteolytic enzymes	Trypsin - Clostridiopeptidase

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Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .