Isosorbide dinitrate

Isosorbide dinitrate

Clinical data
Trade names	Isordil, others
AHFS/Drugs.com	Monograph
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	by mouth
ATC code	C01DA08 (WHO) C05AE02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	10–90%, average 25%
Metabolism	Liver
Biological half-life	1 hour
Excretion	Kidney
Identifiers
IUPAC name 1,4:3,6-dianhydro-2,5-di-O-nitro-D-glucitol
Synonyms	(3R,3aS,6S,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl dinitrate
CAS Number	87-33-2 Y
PubChem CID	6883
DrugBank	DB00883 Y
ChemSpider	6619 Y
UNII	IA7306519N
KEGG	D00516 Y
ChEBI	CHEBI:6061 Y
ChEMBL	CHEMBL2171310 N
ECHA InfoCard	100.001.583
Chemical and physical data
Formula	C6H8N2O8
Molar mass	236.136 g/mol
3D model (Jmol)	Interactive image
SMILES [O-][N+](=O)O[C@H]1[C@H]2OC[C@H](O[N+]([O-])=O)[C@H]2OC1
InChI InChI=1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1 Y Key:MOYKHGMNXAOIAT-JGWLITMVSA-N Y
NY (what is this?)

Isosorbide dinitrate (ISDN) is a medication used for heart failure, esophageal spasms, and to treat and prevent chest pain from not enough blood flow to the heart. It has been found to be particularly useful in heart failure due to systolic dysfunction together with hydralazine in black people. It is taken by mouth or under the tongue.

Common side effects include headache, lightheadedness with standing, and blurred vision. Severe side effects include low blood pressure. It is unclear if use in pregnancy is safe for the baby. It should not be used together with medications within the sildenafil family. ISDN is in the nitrate family of medications and works by dilating blood vessels.

Isosorbide dinitrate was first written about in 1939. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. ISDN is available as a generic medication. The wholesale cost in the developing world is about 6.36 USD a month. In the United States it costs less than 25 USD per month. A long acting form exists.

It is used for angina, in addition to other medications for congestive heart failure, and for esophageal spasms.

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 patients, 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: