16106-20-0

Basic information

• Product Name: ISOSORBIDE 2-MONONITRATE
• Synonyms: IS-2-MN;ISOSORBIDE 2-MONONITRATE;1,4:3,6-dianhydro-,2-nitrate,d-glucito;1,4:3,6-dianhydro-d-glucito2-nitrate;1,4:3,6-dianhydro-d-glucitol2-nitrate;1,4:3,6-dianhydrosorbitol2-mononitrate;2-ismn;isosorbide2-nitrate
• CAS NO: 16106-20-0
• Molecular Formula: C₆H₉NO₆
• Molecular Weight: 191.14
• EINECS: 240-271-4
• Product Categories: Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 16106-20-0.mol

Chemical Properties

• Melting Point: >51.5°C
• Boiling Point: 326.86°C (rough estimate)
• Flash Point: 174.2°C
• Appearance: /
• Density: 1.5784 (rough estimate)
• Vapor Pressure: 8.66E-07mmHg at 25°C
• Refractive Index: 1.4860 (estimate)
• Storage Temp.: -20°C Freezer
• PKA: 13.09±0.40(Predicted)
• CAS DataBase Reference: ISOSORBIDE 2-MONONITRATE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOSORBIDE 2-MONONITRATE(16106-20-0)
• EPA Substance Registry System: ISOSORBIDE 2-MONONITRATE(16106-20-0)

Safety Data

• RTECS: LZ4385500
• Hazardous Substances Data: 16106-20-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Isosorbide 2-mononitrate is used as an antianginal agent for the treatment of angina pectoris. It functions by causing vasodilation, which helps to increase blood flow and reduce the workload on the heart, thereby alleviating the symptoms of angina.
Used in Cardiovascular Applications:
In the field of cardiology, Isosorbide 2-mononitrate is utilized to manage and prevent angina attacks. Its vasodilatory action helps to improve blood flow to the heart muscle, reducing the frequency and severity of angina episodes.
Used in Chronic Stable Angina Treatment:
Isosorbide 2-mononitrate is used as a long-acting medication for the management of chronic stable angina. It is particularly effective in providing relief from chest pain and discomfort associated with physical exertion or emotional stress.
Used in Pulmonary Hypertension Therapy:
In some cases, Isosorbide 2-mononitrate may also be used to treat pulmonary hypertension, a condition characterized by high blood pressure in the arteries of the lungs. Its vasodilatory properties help to reduce the pressure and improve overall lung function.
Overall, Isosorbide 2-mononitrate is a versatile compound with a range of applications in the medical field, primarily focused on cardiovascular health and the treatment of angina pectoris.

InChI:InChI=1/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5-,6-/m1/s1

Upstream product

• 87-33-2 isosorbide dinitrate 
• 7664-93-9 sulfuric acid 
• 79-31-2 isobutyric Acid 
• 652-67-5 Isosorbide 
• 56-23-5 tetrachloromethane 
• 75648-24-7 (3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl benzoate 
• 56389-86-7 (3S,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl benzoate 
• 13042-39-2 isosorbide 2-acetate 
• 13042-38-1 [(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate 
• 84207-83-0 isosorbide 2-O-butanoate 
• 39813-48-4 isosorbide 2-acetate-5-mononitrate 
• 50-70-4 D-sorbitol 

Downstream Products

• 646511-22-0 (1S,2S,5S,6R)-6-(nitrooxy)-4,8-dioxabicyclo(3.3.0)oct-2-yl 2-(1-((4-chlorophenyl)carbonyl)-5-methoxy-2-methylindol-3-yl)acetate 
• 1196117-80-2 (3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl 2-butyl-4-chloro-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate 
• 1609973-49-0 C₁₃H₁₂N₂O₁₀ 
• 1609973-56-9 C₂₇H₃₇N₃O₈S 
• 1609973-51-4 C₂₈H₃₇N₃O₁₁S 
• 1609973-52-5 C₂₈H₃₈N₂O₉S 
• 1609973-54-7 C₂₇H₃₆N₄O₁₀S 
• 1609973-57-0 C₂₇H₃₄N₄O₁₂S 
• 1185768-61-9 (3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl {[(2-butyl-4-chloro-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazol-5-yl)carbonyl]amino}acetate 
• 1196117-75-5 (1S)-1-[({[(3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl]oxy}carbonyl)oxy]ethyl 2-butyl-4-chloro-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate 
• 56389-86-7 (3S,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl benzoate 
• 13042-39-2 isosorbide 2-acetate 
• 75648-24-7 (3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl benzoate 

Related news

Development and validation of a chiral LC-ESI-MS/MS method for simultaneous determination of the enantiomeric metabolites ISOSORBIDE 2-MONONITRATE (cas 16106-20-0) and isosorbide 5-mononitrate of isosorbide dinitrate in rat and human plasma07/16/2019

A specific liquid chromatography–tandem mass spectrometry (LC-ESI-MS/MS) assay was developed and validated for simultaneous determination of two active metabolites of isosorbide dinitrate (ISDN), namely, isosorbide 2-mononitrate (IS 2-MN) and isosorbide 5-mononitrate (IS 5-MN). A simple protein...detailed

Relevant articles and documents

Active oxygen responsive antioxidant nitric oxide donor, and preparation method and application thereof

The invention relates to the field of medicinal chemistry, and especially relates to an active oxygen responsive antioxidant nitric oxide donor, and a preparation method and application thereof. The donor has a structural formula shown in the specification. The preparation method comprises the following steps: reacting PBAP with CDI to obtain PBAP-CDI; and reacting with ISN under the action of a catalyst to obtain the antioxidant nitric oxide donor. The active oxygen responsive antioxidant nitric oxide donor disclosed by the invention is good in stability and long in half-life period in a physiological environment, can be decomposed and released only under the stimulation of high-concentration active oxygen in inflammatory tissues, and does not generate side effects on normal tissues. Meanwhile, active oxygen can be effectively removed, and the anti-oxidation effect is achieved; and the antioxidant nitric oxide donor can promote the growth of endothelial cells and inhibit the growth of smooth muscle cells, is beneficial to rapid endothelialization of heart and blood vessels, has diversified functions, can be widely applied to drug development, and has popularization and application values.

Synthesis method and application of isosorbide mononitrate

The invention belongs to the field of medicine synthesis, and discloses a synthesis method and application of isosorbide mononitrate. The synthesis method of the isosorbide mononitrate provided by the invention adopts a one-pot method and comprises the following steps: adding sorbitol into concentrated sulfuric acid, dehydrating and cyclizing, adding nitrate, carrying out nitration reaction, and adding zinc powder to carry out reduction reaction, thereby obtaining the isosorbide mononitrate. The synthesis method has the advantages of simple process flow, high raw material utilization rate and production cost saving. The method is suitable for synthesizing the isosorbide mononitrate, and the obtained isosorbide mononitrate is used for preparing the isosorbide mononitrate for injection.

A 5 - isosorbide Mononitrate preparation method (by machine translation)

The present invention provides a 5 - isosorbide Mononitrate synthetic method. The method includes the steps of: in order to isosorbide as raw materials, with the nitrates TMSCl nitrating agent in three of the aluminum chloride under the action of selective nitration sorbitan 5 - hydroxyl, completion of the reaction, the reaction liquid is poured into ice water, adjusting the pH value to neutral, filtering precipitation, phase separation, the aqueous phase of the liquid organic solvent extraction, the organic phase into the drying agent and, decolorized with active carbon, concentrated under reduced pressure to dry, to obtain high-purity of 5 - isosorbide Mononitrate. The scheme of this invention mild reaction conditions, nitration high selectivity, after treatment is simple, high product yield and purity, is suitable for industrial production. (by machine translation)

An Improved Process for Industrial Production of Isosorbide-5-mononitrate: Recycling of Wastes

Different schemes were studied for the recovery of wastes generated during the industrial production of isosorbide-5-mononitrate (IS-5-MN). For the wastewater, disposal was achieved by hydrolysis of isosorbide-2-mononitrate (IS-2-MN) to the starting material isosorbide (IS) utilizing its alkaline environment, where NaOAc was also recovered effectively in the form of the trihydrate. For the solid waste, two different schemes were investigated: direct crystallization and catalytic hydrogenation. The former afforded useful isosorbide dinitrate (ISDN) efficiently, and the latter provided an efficient and scalable route to synthesize IS-5-MN from ISDN. The combinations of unit operations were evaluated on a 100 kg scale and proved to be feasible and robust. The waste recycling strategy provides an eco-friendly complement for the industrial-scale preparation of IS-5-MN, which minimizes waste emission during the process.

Method for synthesizing 5-isosorbide mononitrate by aid of micro-channel reactors

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.

Preparation method of 5-isosorbide mononitrate

The invention provides a preparation method of 5-isosorbide mononitrate. The synthetic method comprises the following steps: selectively nitrating 5-site hydroxyl radicals in a dried organic solvent by taking sorbitan as a raw material and a silver nitrate/sulfoxide chloride system as a nitrating agent, after the reaction is finished, carrying out suction filtration on reaction liquid, filtering precipitates, pouring filtrate into water, washing the filtrate to be neutral, adding a drying agent into an organic phase for drying, carrying out activated carbon decoloration, and carrying out reduced pressure concentration until the liquid is dried, so as to obtain high-purity 5-isosorbide mononitrate. The scheme provided by the invention has the beneficial effects that reaction conditions are mild, the nitrating selectivity is high, post-treatment is simple, the yield and purity of a product are high, and the preparation method is suitable for industrial production.

A 5 - isosorbide Mononitrate preparation method

The invention provides a preparation method for isosorbide 5-mononitrate. The preparation method comprises the following steps: with isosorbide dinitrate as a raw materials and Pd/C as a catalyst in a special mixed solvent, carrying out selective hydrogenation reduction on 2-nitro, filtering after reaction, steaming to remove ethyl alcohol in filtrate, extracting residual concentrated liquid through ethyl acetate, washing extracting liquid through dilute acid, washing to be neutral through water, drying through anhydrous magnesium sulfate, filtering to remove a drying agent and steaming to remove ethyl acetate so as to obtain high-purity isosorbide 5-mononitrate. Compared with the prior art, the synthetic method provided by the invention is simple and easy to operate, impurities are easy to remove, the yield and purity are higher, the cost is reduced since the Pd/C and the solvent can be recycled and reused, isosorbide generated through over reduction can be recycled and the preparation method is suitable for industrial production.

A 5-isosorbide Mononitrate the synthesis and purification method

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.

Synthesis of 2-[18F]Fluoro-2-deoxyisosorbide 5-mononitrate and Assessment of Its in vivo Biodistribution as Determined by Dynamic Positron Emission Tomography (PET)

Herein we disclose the synthesis of 2-fluoro-2-deoxyisosorbide 5-mononitrate (2F-IS-5MN), a fluorinated analogue of the commonly prescribed vasodilator isosorbide 5-mononitrate (IS-5MN). X-ray structural data for IS-5MN and its C2-epimeric congener IM-5MN are presented together with structural data for 2F-IS-5MN. Radioisotope labeling of 2F-IS-5MN has, for the first time, allowed observation of the in vivo biodistribution of this organic nitrate by means of dynamic positron emission tomography (PET) in wild-type mice. Visualization breakthrough: Herein we disclose the synthesis of a fluorinated analogue of the commonly prescribed vasodilator isosorbide 5-mononitrate (IS-5MN). Radioisotope labeling of 2F- IS-5MN has, for the first time, allowed observation of the in vivo biodistribution of this organic nitrate by means of dynamic positron emission tomography (PET) in wild-type mice.

VASODILATOR-ENHANCED CARDIOPULMONARY RESUSCITATION

A method for increasing blood flow to vital organs during cardiopulmonary resuscitation of a person experiencing a cardiac arrest may include performing standard or active compression decompression cardiopulmonary resuscitation on a person to create artificial circulation by repetitively compressing the person's chest such that the person's chest is subject to a compression phase and a relaxation or decompression phase. The method may also include administering one or more vasodilator drugs to the person to improve the artificial circulation created by the cardiopulmonary resuscitation. The method may also include binding at least a portion of the person's abdomen, either manually or with an abdominal compression device. Performing cardiopulmonary resuscitation on a person may include ventilating the person with either an impedance threshold device or a intrathoracic pressure regulator.