Chemical Properties
white to light yellow crystal powde
Originator
Isordil,Ives,US,1959
Uses
Isosorbide dinitrate is also used in chronic cardiac insufficiency for preventing angina pectoris
attacks. It is a long-lasting drug.
Uses
Antianginal;Nitric oxide (NO) donor
Uses
Coronary vasodilator
Definition
ChEBI: Isosorbide dinitrate is a nitrate ester and a glucitol derivative. It has a role as a vasodilator agent and a nitric oxide donor.
Manufacturing Process
An aqueous syrup of 1,4:3,6-dianhydro-D-glucitol is slowly added to a cooled
mixture of HNO3 and H2SO4. After standing a few minutes the mixture is
poured into cold water and the precipitated product is collected and
recrystallized from ethanol.
brand name
Dilatrate (Schwarz Pharma); Isordil (Biovail);
Isordil (Wyeth); Sorbitrate (AstraZeneca).
Therapeutic Function
Coronary vasodilator
General Description
A crystalline solid. May be toxic by ingestion. Used to make pharmaceuticals. Used as a heart drug.
Air & Water Reactions
Highly flammable. Slightly soluble in water.
Reactivity Profile
Nitroalkanes, such as Isosorbide dinitrate, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. Nitroalkanes are milder oxidizing agents, but still react violently with reducing agents at higher temperature and pressures. Nitroalkanes react with inorganic bases to form explosive salts. The presence of metal oxides increases the thermal sensitivity of nitroalkanes. Nitroalkanes with more than one nitro group are generally explosive. Nitroalkanes are insoluble in water. This heart drug is detonable when dry, but non-explosive with 30% of water.
Health Hazard
Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.
Fire Hazard
Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished.
Clinical Use
Vasodilator:
Prophylaxis and treatment of angina
Left ventricular failure
Safety Profile
Moderately toxic by
ingestion, intraperitoneal, intramuscular, and
subcutaneous routes. Experimental
reproductive effects. Mutation data
reported. A flammable solid. When heated
to decomposition it emits toxic fumes of
NOx. A coronary vasodilator. See also
NITRATES.
Synthesis
Isosorbiddinitrate, 1,4:3,6-dianhydrosorbate-2,5-dinitrate (19.1.4), is
synthesized by intermolecular dehydration of D-sorbite into isosorbide (19.1.3) using paratoluenesulfonic
acid and subsequent nitration of the two hydroxyl groups by nitric acid.
Veterinary Drugs and Treatments
Isosorbide mononitrate (ISMN) and dinitrate (ISDN) are organic
nitrates potentially useful as preload reducing agents in treating
heart failure in small animals, however, research and clinical experience
demonstrating clinical efficacy are lacking in dogs or cats.
Limited research indicates that dogs may require much higher dosages
of isosorbide dinitrate to achieve therapeutic effects than do
humans.
In humans, isosorbide nitrates are used for treating or preventing
angina, treating esophageal spasm, and as an adjunctive treatment
in CHF.
