isosorbide dinitrate
isosorbide dinitrate
CAS: 87-33-2
Molecular Formula: C6H8N2O8
isosorbide dinitrate - Names and Identifiers
| Name | isosorbide dinitrate |
| Synonyms | cardis carvasin carvanil sorbide nitrate Isosobide dinitrate isosorbide dinitrate Isosorbitol dinitrate [(3S,3aS,6R,6aS)-6-Nitrooxy-2,3,3a,5,6,6a-hexahydrofuro[2,3-d]furan-3-yl] nitrate |
| CAS | 87-33-2 |
| EINECS | 201-740-9 |
| 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 |
| InChIKey | MOYKHGMNXAOIAT-JGWLITMVSA-N |
isosorbide dinitrate - Physico-chemical Properties
| Molecular Formula | C6H8N2O8 |
| Molar Mass | 236.14 |
| Density | 1.7503 (rough estimate) |
| Melting Point | 700C |
| Boling Point | 378.59°C (rough estimate) |
| Specific Rotation(α) | D20 +135° (alc) |
| Flash Point | 186.6°C |
| Water Solubility | 549.7mg/L(25 ºC) |
| 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. |
| Vapor Presure | 3.19E-05mmHg at 25°C |
| Appearance | neat |
| Color | White to Off-White |
| Storage Condition | -20°C Freezer |
| Refractive Index | 1.5010 (estimate) |
| Physical and Chemical Properties | White crystalline powder. Melting point 70 ° C, soluble in chloroform, acetone, slightly soluble in ethanol, water-soluble. Odorless. Less explosive than nitroglycerin. |
| Use | Coronary vasodilators for the treatment of angina pectoris |
isosorbide dinitrate - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R5 - Heating may cause an explosion R22 - Harmful if swallowed |
| Safety Description | 36 - Wear suitable protective clothing. |
| UN IDs | UN 2907 |
| HS Code | 2932999000 |
| Hazard Class | 4.1 |
| Packing Group | II |
| Toxicity | LD50 oral in rat: 747mg/kg |
isosorbide dinitrate - Reference Information
| LogP | 1.31 at 25℃ |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | isosorbide dinitrate was marketed in Sweden in 1946 under the trade name Harrical in the form of tablets and ointments, in the 50 s, American chemists also synthesized isosorbide dinitrate independently. The trade name Isordil has been widely used in the world since then. Isosorbide dinitrate (ISDN) also known as isosorbide dinitrate, sorbitan nitrate, isosorbide dinitrate, etc. |
| mechanism of action | The study on the mechanism of action of nitrate ester also shows that its anti-angina mechanism is complex, in general, the mechanism of action of Isosorbide Dinitrate on angina pectoris has the following aspects:(1) reduce myocardial oxygen consumption. Nitrates dilate the venous vessels and increase the venous volume, thereby reducing the amount of return blood to the heart, reducing the cardiac volume, reducing the tension of the myocardial wall and shortening the ejection time; In addition, dilating the arterial vessels and reducing the afterload of the left ventricle, so as to achieve the purpose of reducing myocardial oxygen consumption. (2) the redistribution of myocardial blood flow is beneficial to the perfusion of ischemic area. Nitrates selectively dilate large coronary artery delivery vessels, increase the flow of ischemic area; Reduce left ventricular filling pressure, increase endocardial blood supply, improve left ventricular compliance; Also stimulate the formation of collateral, open the existing collateral, increased nutrient perfusion in ischemic areas. (3) in atherosclerosis or acute ischemia, endothelial cells can not release NO and PGI; But accelerate platelet aggregation and vascular endothelial cells release contractile substances. Exogenous nitrate can supplement the deficiency of endogenous NO and promote the release of PGI. Nitrate itself has significant anti-platelet aggregation and anti-thrombosis effects. NO is known to be an important biological messenger molecule and effector molecule, and nitrates are one of the NO donor drugs. |
| indication | This product is mainly used for long-term treatment and prevention of coronary heart disease, it is also suitable for the treatment of myocardial infarction and long-term treatment of chronic heart failure. |
| pharmacokinetics | isosorbide dinitrate is completely absorbed after oral administration, but the first-pass effect in the liver is more significant, is metabolized to 2-mononitrate Isosorbide and 5-mononitrate isosorbide. Plasma half-life of 30~60min, because of the significant first pass effect and short half-life, Isosorbide nitrate is more suitable for sustained-release preparation. The absorption phase of isosorbide dinitrate sustained-release preparation was significantly prolonged, the peak time was delayed, the peak concentration was lower, the concentration of isosorbide dinitrate and its metabolites in plasma changed gently with time, and the hemodynamic effect was relatively stable. The patient discomfort caused by the "burst release" of the common preparation can be overcome, and the sustained-release preparation of isosorbide dinitrate can reduce the number of administration and improve the compliance. |
| preparation | a sorbitol solution was obtained by dehydration cyclization and esterification with nitric acid. The details are as follows: 50g fuming nitric acid and 7.5g concentrated sulfuric acid are added to a reaction bottle equipped with a stirrer and thermometer, and the mixture is cooled to 10 ° C, the liquid obtained by slightly heat dissolving 10g of solid Sorbitan and 1ml of water was slowly added dropwise, the temperature of the reaction solution was maintained at 10-15 ° C., and the reaction was maintained for 2 hours after the addition. The reactant was poured into 7 times the amount of ice water with stirring, and the crystals were sufficiently stirred for crystallization. Suction filtration, washing to neutral, dry, crude product. The crude product was added to 1.5 times the amount of 95% ethanol, heated and dissolved, and the activated carbon was decolorized and refluxed for 30min. Hot Suction filtration, cold to below 10 ℃, Suction filtration precipitation of crystals, ethanol washing, low temperature drying, Isosorbide nitrate ester, yield 70%. |
| adverse reaction | was lighter than nitroglycerin. Common Head Pain, facial flushing, dizziness, Nausea, sometimes the occurrence of postural hypotension, occasionally rash and even exfoliative dermatitis. |
| Use | This product is a quick-acting, long-acting nitrates anti-anginal drug with the same effect as nitroglycerin, mainly used for the prevention of heart before the onset, can also be used to relieve symptoms. coronary vasodilator for angina pectoris |
| production method | The sorbitol solution is obtained by dehydration cyclization and esterification with nitric acid. |
| category | flammable solid |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 747 mg/kg; Oral-mouse LD50: 1050 mg/kg |
| stimulation data | Skin-rabbits 500 mg/24 h mild |
| flammability hazard characteristics | when exposed to heat, the flame is flammable; Thermal decomposition emits toxic nitrogen oxide smoke |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; Fire-proof; Stored separately from oxidant |
| extinguishing agent | water, carbon dioxide, foam, dry powder |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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View History
isosorbide dinitrate
3-[(4-(4-[2-(PHENYLSULFONYL)ETHYL]PIPERAZIN-1-YL)PIPERIDIN-1-YL)METHYL]BENZONITRILE HYDROCHLORIDE
依玛鲁单抗
Bromocresol Green
RAF1 KINASE INHIBITOR I
BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID
Valeric acid 1-methylethyl ester
6-TAMRA 6羧基四甲基罗丹明马来酰亚胺
3β.6β-Dihydroxy-Δ4-cholansaeure
PALMITIC ACID OLEYL ESTER
3-[(4-(4-[2-(PHENYLSULFONYL)ETHYL]PIPERAZIN-1-YL)PIPERIDIN-1-YL)METHYL]BENZONITRILE HYDROCHLORIDE
依玛鲁单抗
Bromocresol Green
RAF1 KINASE INHIBITOR I
BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID
Valeric acid 1-methylethyl ester
6-TAMRA 6羧基四甲基罗丹明马来酰亚胺
3β.6β-Dihydroxy-Δ4-cholansaeure
PALMITIC ACID OLEYL ESTER