Isosorbide dinitrate

Isosorbide dinitrate Basic information
Product Name:Isosorbide dinitrate
Synonyms:isosorbide dinitrates;Isosorbide USP2000,BP98;Isosorbide Dinitrate 40% EU or BP;ISOSORBIDE DINITRATE, EP STANDARD;ISOSORBIDE DINITRATE, 97+%;ISOSORBIDE DINITRATE(CONTAINS APPROX. 60% LACTOSE) MM(CRM STANDARD);ISOSORBIDE DINITRATE, USP23 50%;ISOSORBIDE DINITRATE IMP. B (EP): ISOSORBIDE 2-NITRATE MM(CRM STANDARD)
CAS:87-33-2
MF:C6H8N2O8
MW:236.14
EINECS:201-740-9
Product Categories:chiral;Nitric Oxide Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;87-33-2
Mol File:87-33-2.mol
Isosorbide dinitrate Structure
Isosorbide dinitrate Chemical Properties
Melting point 700C
alpha D20 +135° (alc)
Boiling point 378.59°C (rough estimate)
density 1.7503 (rough estimate)
refractive index 1.5010 (estimate)
storage temp. -20°C Freezer
solubility Undiluted isosorbide dinitrate is very slightly soluble in water, very soluble in acetone, sparingly soluble in ethanol (96 per cent). The solubility of the diluted product depends on the diluent and its concentration.
form neat
color White to Off-White
Water Solubility 549.7mg/L(25 ºC)
BCS Class3
InChIKeyMOYKHGMNXAOIAT-JGWLITMVSA-N
LogP1.31 at 25℃
CAS DataBase Reference87-33-2(CAS DataBase Reference)
EPA Substance Registry SystemD-Glucitol, 1,4:3,6-dianhydro-, dinitrate (87-33-2)
Safety Information
Hazard Codes Xn
Risk Statements 5-22
Safety Statements 36
RIDADR UN 2907
HazardClass 4.1
PackingGroup II
HS Code 2932999000
Hazardous Substances Data87-33-2(Hazardous Substances Data)
ToxicityLD50 oral in rat: 747mg/kg
MSDS Information
ProviderLanguage
Dilatrate-SR English
Isosorbide dinitrate Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powde
OriginatorIsordil,Ives,US,1959
UsesIsosorbide dinitrate is also used in chronic cardiac insufficiency for preventing angina pectoris attacks. It is a long-lasting drug.
UsesAntianginal;Nitric oxide (NO) donor
UsesCoronary vasodilator
DefinitionChEBI: Isosorbide dinitrate is a nitrate ester and a glucitol derivative. It has a role as a vasodilator agent and a nitric oxide donor.
Manufacturing ProcessAn 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 nameDilatrate (Schwarz Pharma); Isordil (Biovail); Isordil (Wyeth); Sorbitrate (AstraZeneca).
Therapeutic FunctionCoronary vasodilator
General DescriptionA crystalline solid. May be toxic by ingestion. Used to make pharmaceuticals. Used as a heart drug.
Air & Water ReactionsHighly flammable. Slightly soluble in water.
Reactivity ProfileNitroalkanes, 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 HazardFire 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 HazardFlammable/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 UseVasodilator:
Prophylaxis and treatment of angina
Left ventricular failure

Safety ProfileModerately 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.
SynthesisIsosorbiddinitrate, 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.

Synthesis_87-33-2

Veterinary Drugs and TreatmentsIsosorbide 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.
Isosorbide dinitrate Preparation Products And Raw materials
Raw materialsSorbitol-->D-Sorbitol-->SORBITOL SOLUTION 70-->Nitric acid-->Isosorbide
Preparation ProductsIsosorbide 5-mononitrate
ISOSORBIDE 2-MONONITRATE Prenyl acetate ISOSORBIDE DINITRATE PELLETES 1-Butyl nitrite ISOSORBIDE DINITRATE IMP. C (EP): ISOSORBIDE MONONITRATE(ISOSORBIDE 5-NITRATE) Pentyl nitrite D-isosorbide dinitrate-lactose mixture 2:3,D-Isosorbide dinitrate-Lactose mixture,D-ISOSORBIDE DINITRATE Isosorbide dinitrate U.S.P24,BP98,Diluted isosorbide dinitrate ISOSORBIDE DINITRATE, 25% MANNITOL Isosorbide dinitrate mixture with not less than 60% lactose,mannose,starch or calcium hydrogen phosphate,Mixed isosorbide dinitrate ISOPROPYL NITRITE 1-MONONITROGLYCERIN ISOSORBIDE-13C6 DINITRATE 2-MONONITROGLYCERIN Isosorbide Dinitrate(25 kg) ISOSORBIDE MONONITRATE IMP. B (EP): ISOSORBIDE DINITRATE (CONTAINS APPROX. 60% LACTOSE) MM(CRM STANDARD) SEC-BUTYL NITRITE ISOSORBIDE MONONITRATE IMP. B (EP): ISOSORBIDE DINITRATE (CONTAINS APPROX. 60% LACTOSE)

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