16051-77-7

Basic information

• Product Name: Isosorbide 5-mononitrate
• Synonyms: IMDUR;IS-5-MN;ISOSORBIDE MONONITRATE;ISOSORBIDE 5-MONONITRATE;ISOSORBIDE 5-NITRATE;ELANTAN;ELAN;CORANGIN
• CAS NO: 16051-77-7
• Molecular Formula: C₆H₉NO₆
• Molecular Weight: 191.14
• EINECS: 240-197-2
• Product Categories: chiral;Nitric Oxide Reagents;Various Metabolites and Impurities;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;API's;LEXAPRO
• Mol File: 16051-77-7.mol
• Article Data: 25

Chemical Properties

• Melting Point: 88-93 °C
• Boiling Point: 326.86°C (rough estimate)
• Flash Point: 174.2 °C
• Appearance: white to light yellow crystal powder
• Density: 1.5784 (rough estimate)
• Refractive Index: 145 ° (C=5, H2O)
• Storage Temp.: -20°C Freezer
• Solubility: Undiluted isosorbide mononitrate is freely soluble in water, in acetone, in ethanol (96 per cent) and in methylene chloride. The solubility of the diluted product depends on the diluent and its concentration.
• PKA: 13.09±0.40(Predicted)
• Water Solubility: soluble
• Merck: 5225
• CAS DataBase Reference: Isosorbide 5-mononitrate(CAS DataBase Reference)
• NIST Chemistry Reference: Isosorbide 5-mononitrate(16051-77-7)
• EPA Substance Registry System: Isosorbide 5-mononitrate(16051-77-7)

Safety Data

• Hazard Codes: Xi-F,Xi,F
• Statements: 36/37/38-11
• Safety Statements: 37/39-16-15
• RIDADR: 3251
• RTECS: LZ4386500
• HazardClass: 1.1A
• Hazardous Substances Data: 16051-77-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 16051-77-7 differently. You can refer to the following data:
1. Isosorbide 5-Mononitrate is a metabolite of Isosorbide Dinitrate; used as an antianginal.
2. antidepressant, 5HT reuptake inhibitor
3. A metabolite of Isosorbide Dinitrate. Used as an antianginal

Brand name

Imdur (Schering-Plough); Ismo (Dr. Reddy’s); Monoket (Schwarz Pharma) .

General Description

Isosorbide 5-mononitrate is a crystalline solid. Isosorbide 5-mononitrate is very flammable and may be toxic by ingestion.

Air & Water Reactions

Highly flammable.

Reactivity Profile

The dinitrate, a heart drug, can detonate when dry, but is non explosive with 30% of water [J. Haz.. Mater., 1992, 32(1), 87]. The mononitrate would be expected to be less reactive.

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: Treatment and prophylaxis of angina Adjunct in congestive heart failure

Drug interactions

Potentially hazardous interactions with other drugs Avanafil: hypotensive effect significantly enhanced - avoid. Levosimendan: possible severe hypotension. Riociguat: avoid concomitant use due to risk of hypotension. Sildenafil: hypotensive effect significantly enhanced - avoid. Tadalafil: hypotensive effect significantly enhanced - avoid. Vardenafil: hypotensive effect significantly enhanced - avoid.

Metabolism

Unlike isosorbide dinitrate, isosorbide mononitrate does not undergo first-pass hepatic metabolism. Isosorbide mononitrate is taken up by smooth muscle cells of blood vessels and the nitrate group is cleaved to inorganic nitrite and then to nitric oxide. Isosorbide mononitrate is metabolised to inactive metabolites, including isosorbide and isosorbide glucuronide

InChI:InChI=1/C6H7NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h4-6H,1-2H2/t4-,5+,6+/m1/s1

Upstream product

• 87-33-2 isosorbide dinitrate 
• 56389-86-7 (3S,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl benzoate 
• 75648-24-7 (3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl benzoate 
• 39813-48-4 isosorbide 2-acetate-5-mononitrate 
• 50-70-4 D-sorbitol 
• 652-67-5 Isosorbide 
• 65940-93-4 (6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate 
• 39698-15-2 5-O-acetyl-2-isosorbide nitrate 
• 13042-39-2 isosorbide 2-acetate 
• 56-23-5 tetrachloromethane 
• 7664-93-9 sulfuric acid 
• 79-31-2 isobutyric Acid 
• 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 

Downstream Products

• 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 
• 652-67-5 Isosorbide 
• 847202-70-4 ethyl (2S)-2-(((1S)-2-((2S)-2-(((1S,2S,5S,6R)-6-(nitrooxy)-4,8-dioxabicyclo(3.3.0)oct-2-yl)oxycarbonyl)pyrrolidinyl)-1-methyl-2-oxoethyl)amino)-4-phenylbutanoate 
• 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 
• 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 
• 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 
• 1072106-21-8 2-(benzylaminocarbonyloxy)-1,4:3,6-dianhydro-D-glucitol 

Relevant articles and documents

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.

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.

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.