87-33-2 Usage
Chemical Properties
white to light yellow crystal powde
Originator
Isordil,Ives,US,1959
Uses
Different sources of media describe the Uses of 87-33-2 differently. You can refer to the following data:
1. Isosorbide dinitrate is also used in chronic cardiac insufficiency for preventing angina pectoris
attacks. It is a long-lasting drug.
2. Antianginal;Nitric oxide (NO) 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).
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 87-33-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 87-33:
(4*8)+(3*7)+(2*3)+(1*3)=62
62 % 10 = 2
So 87-33-2 is a valid CAS Registry Number.
InChI:InChI=1/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
87-33-2Relevant articles and documents
METHOD FOR PREPARING NITRATE ESTER
-
Paragraph 0026-0030, (2020/05/29)
A method for preparing a nitrate ester is provided. The method includes providing a first solution including a compound (which has at least one hydroxyl group) and a carboxylic acid having 2-5 carbon atoms; providing a second solution including nitric acid, acetic anhydride, and acetic acid; and transferring the first solution and the second solution to a microreactor, obtaining a nitrate ester after a residence time. In particular, the ratio of the weight of nitric acid to the total volume of the acetic anhydride and acetic acid is 1:1 to 1:3.5. The ratio of the molar amount of nitric acid to the hydroxyl group equivalent of the compound is from 1:1 to 15:1.
Method for synthesizing 5-isosorbide mononitrate by aid of micro-channel reactors
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Paragraph 0048-0078; 0095; 0097, (2018/10/19)
The invention belongs to the field of medicine synthesis, and particularly discloses a method for synthesizing 5-isosorbide mononitrate by the aid of micro-channel reactors. The method includes pumping nitrification reagents and isosorbide liquid into the micro-channel reactors and carrying out hybrid reaction; allowing products to flow out from outlets of the micro-channel reactors after the reaction is completely carried out; carrying out after-treatment on the products and separating and purifying the products to obtain the 5-isosorbide mononitrate which is a target product. The method hasthe advantages that the method is short in reaction time and is safe as compared with the traditional processes, and the yield of the 5-isosorbide mononitrate can be greatly increased.
A 5-isosorbide Mononitrate the synthesis and purification method
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Paragraph 0045-0051, (2017/01/23)
The invention provides a method for synthesizing and purifying 5-isosorbide mononitrate. The method comprises the steps of: (1) preparing a nitrifying reagent from concentrated nitric acid, acetic acid and acetic anhydride, and directly nitrifying isosorbide to obtain an isosorbide nitride mixture; (2) adding water to arouse a quenching reaction, separating out 2,5-isoscrbide dinifrate at a temperature ranging from 0 to 5 DEG C, and filtering out the 2,5-isoscrbide dinifrate; (3) reacting the filtrate with sodium hydroxide to prepare an isosorbide mononitrate sodium salt aquo-complex, filtering, and hydrolyzing the sodium salt; and (4) extracting, concentrating and recrystallizing to obtain high-purity 5-isosorbide mononitrate. The preparation method provided by the invention is simple, safe, easy to operate and short in reaction period; impurities are easy to remove, and the yield and the purity are high; therefore, the method lays a foundation for industrial production.