General Description
A crystalline solid. May be toxic by ingestion. Used to make pharmaceuticals. Used as a heart drug.
Reactivity Profile
Nitroalkanes, such as ISOSORBIDE DINITRATE MIXTURE(87-33-2), 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.
Air & Water Reactions
Highly flammable. Slightly soluble in 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.
Chemical Properties
white to light yellow crystal powde
Originator
Isordil,Ives,US,1959
Uses
Antianginal;Nitric oxide (NO) donor
Uses
Coronary vasodilator
Uses
Isosorbide dinitrate is also used in chronic cardiac insufficiency for preventing angina pectoris
attacks. It is a long-lasting drug.
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
Clinical Use
Vasodilator:
Prophylaxis and treatment of angina
Left ventricular failure
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.
Drug interactions
Potentially hazardous interactions with other drugs
Avanfil, sildenafil, tadalafil, vardenafil: hypotensive
effect significantly enhanced - avoid concomitant
use.
Riociguat: avoid concomitant use due to risk of
hypotension.
Metabolism
Isosorbide dinitrate undergoes extensive first-pass
metabolism in the liver. It is taken up by smooth muscle
cells of blood vessels and the nitrate group is cleaved
to inorganic nitrite and then to nitric oxide. It is also
rapidly metabolised in the liver to the major active
metabolites isosorbide 2-mononitrate and isosorbide
5-mononitrate. Isosorbide mononitrate is metabolised to
inactive metabolites, including isosorbide and isosorbide
glucuronide. Only about 2% of isosorbide mononitrate is
excreted unchanged in the urin
storage
4°C, protect from light