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Isosorbide dinitrate

Isosorbide dinitrate
Systematic (IUPAC) name
(3R,3aS,6S,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl dinitrate
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.


Legal status

Prescription only

Routes Oral

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.



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.


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


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 a 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.


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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Isosorbide_dinitrate". A list of authors is available in Wikipedia.
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