Isosorbide mononitrate

Base Information

• Chemical Name: Isosorbide mononitrate
• CAS No.: 16051-77-7
• Molecular Formula: C6H9NO6
• Molecular Weight: 191.141
• Hs Code.: 3003.90
• European Community (EC) Number: 240-197-2
• NSC Number: 758619
• UN Number: 3251
• UNII: LX1OH63030
• DSSTox Substance ID: DTXSID9023176
• Wikipedia: Isosorbide_mononitrate
• Wikidata: Q423401
• NCI Thesaurus Code: C47575
• RXCUI: 28004
• Pharos Ligand ID: YJ3P9WPZHQZJ
• Metabolomics Workbench ID: 43264
• ChEMBL ID: CHEMBL1311
• Mol file: 16051-77-7.mol

Synonyms:5-ISMN;5-ISMN Durules;Elantan;Imdur;Ismo;isosorbide mononitrate;isosorbide-5-mononitrate;isosorbide-5-nitrate;Monizid;Mono Mac 50D;monocinque;Monoket;Mononit;Olicard 40;Olicard-retard

Chemical Property of Isosorbide mononitrate

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 88-93 °C
• Refractive Index: 145 ° (C=5, H2O)
• Boiling Point: 364.5 °C at 760 mmHg
• PKA: 13.09±0.40(Predicted)
• Flash Point: 174.2 °C
• PSA: 93.74000
• Density: 1.56 g/cm³
• LogP: -0.75500
• 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.
• Water Solubility.: soluble
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 191.04298701
• Heavy Atom Count: 13
• Complexity: 216
• Transport DOT Label: Flammable Solid

Purity/Quality:

99% ^*data from raw suppliers

Isosorbide5-Mononitrate(1.0mg/mLinDimethylSulfoxide) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi-F,Xi,F
• Statements: 36/37/38-11
• Safety Statements: 37/39-16-15

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2C(O1)C(CO2)O[N+](=O)[O-])O
• Isomeric SMILES: C1[C@@H]([C@@H]2[C@H](O1)[C@@H](CO2)O[N+](=O)[O-])O
• Recent ClinicalTrials: Isosorbide Mononitrate For Anti-Vascular Endothelial Growth Factor (VEGF) Induced Kidney Injury
• Recent EU Clinical Trials: LACunar Intervention (LACI-2) Trial-2: Assessment of safety and efficacy of cilostazol and isosorbide mononitrate to prevent recurrent lacunar stroke and progression of cerebral small vessel disease.
• Recent NIPH Clinical Trials: Clinical trial of effects of isosorbide mononitrate on vascular function
• Uses: Isosorbide 5-Mononitrate is a metabolite of Isosorbide Dinitrate; used as an antianginal. antidepressant, 5HT reuptake inhibitor A metabolite of Isosorbide Dinitrate. Used as an antianginal
• 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.

Technology Process of Isosorbide mononitrate

There total 35 articles about Isosorbide mononitrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

Isosorbide (652-67-5) → isosorbide mononitrate (16106-20-0,16908-90-0,16908-91-1,35993-37-4,38709-03-4,114718-64-8,127001-76-7,16051-77-7)

Guidance literature:

Isosorbide; With chloro-trimethyl-silane; triethylamine; at -5 ℃; for 0.5h;

With aluminum (III) chloride; sodium nitrate; at -5 ℃; for 2h; Reagent/catalyst; Temperature;

Reference yield: 91.0%

isosorbide 2-acetate-5-mononitrate (39813-48-4) → isosorbide mononitrate (16106-20-0,16908-90-0,16908-91-1,35993-37-4,38709-03-4,114718-64-8,127001-76-7,16051-77-7)

Guidance literature:

With potassium carbonate; In methanol; water;

Reference yield: 85.0%

(3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl benzoate (75648-24-7) → isosorbide mononitrate (16106-20-0,16908-90-0,16908-91-1,35993-37-4,38709-03-4,114718-64-8,127001-76-7,16051-77-7)

Guidance literature:

With potassium hydroxide; In ethanol; at 50 ℃; for 0.333333h;

DOI:10.1002/cmdc.201500275

upstream raw materials:

D-sorbitol

isosorbide 2-acetate-5-mononitrate

isosorbide dinitrate

isosorbide 2-O-butanoate

Downstream raw materials:

(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

Isosorbide

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

Refernces

• 1、 -. "Synthesis method and application of isosorbide mononitrate". Paragraph 0032-0040. . Retrieved 2021/07/14.
• 2、 -. "A 5 - isosorbide Mononitrate preparation method (by machine translation)". Paragraph 0020; 0037-0052. . Retrieved 2019/11/14.