(3R,3aS,6S,6aS)-6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl nitrate

• ChemBase ID: 761
• Molecular Formular: C6H8N2O8
• Molecular Mass: 236.13632
• Monoisotopic Mass: 236.02806523
• SMILES: O1[C@H]2[C@H](OC[C@H]2O[N+](=O)[O-])[C@@H](O[N+](=O)[O-])C1
• Canonical SMILES: [O-][N+](=O)O[C@@H]1CO[C@H]2[C@@H]1OC[C@@H]2O[N+](=O)[O-]
• InChI: InChI=1S/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

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,3aS,6S,6aS)-6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl nitrate
• IUPAC Traditional name: isosorbide dinitrate
• Brand Name: Cardio 10; Cardis; Carvanil; Carvasin; Cedocard; Claodical; Cornilat; Coronex; Corosorbide; Difutrat; Dilatrate; Dilatrate-SR; Dinitrosorbide; Emoper; Flindix; Harrical; IBD 20; ISD; ISDN; Ismotic; Iso-Bid; Isochron; Isoket; Isorbid; Isordil; Isordil Tembids; Isostat; Isotrate; Korodil; Lomilan; Maycor; Myorexon; Nitrosorbid; Nitrosorbide; Nitrosorbon; Nosim; Resoidan; Rifloc Retard; Rigedal; Sorbangil; Sorbide T.D.; Sorbidilat; Sorbislo; Sorbitrate; Sorbonit; Sorquad; Tinidil; Titradose; Vascardin; Vasodilat; Vasorbate; Xanyl
• Synonyms: Dianhydrosorbitol 2,5-dinitrate; Sorbide nitrate; Sorbide, dinitrate; Sorbidnitrate; Isosorbide Dinitrate; 1,4:3,6-Dianhydro-D-glucitol Dinitrate; Dinitrosorbide; 1,4:3,6-Dianhydrosorbitol 2,5-Dinitrate, Carvasin; Cedocard; Corovliss; Dignonitrat; Dilatrate; Diniket, ISDN

Database IDs

• CAS Number: 87-33-2
• PubChem SID: 46506412; 160964224
• PubChem CID: 6883

CALCULATED PROPERTIES

JChem

• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 0.4432914
• LogD (pH = 7.4): 0.4432914
• Log P: 0.4432914
• Molar Refractivity: 44.7714 cm^3
• Polarizability: 17.58034 Å^3
• Polar Surface Area: 128.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.87
• LOG S: -2.4
• Solubility (Water): 9.38e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.55 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Acetone; Chloroform; Ethyl Ether; Methanol
• Apperance: White Solid
• Melting Point: 62-64°C
• Hydrophobicity(logP): 1.31 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB00883

• Drug Groups: approved
• Description: A vasodilator used in the treatment of angina pectoris. Its actions are similar to nitroglycerin but with a slower onset of action. [PubChem]
• Indication: For the prevention of angina pectoris due to coronary artery disease.
• Pharmacology: Isosorbide Dinitrate is a moderate to long acting oral organic nitrate used for the relief and prophylactic management of angina pectoris. It relaxes the vascular smooth muscle and consequent dilatation of peripheral arteries and veins, especially the latter. Dilatation of the veins promotes peripheral pooling of blood and decreases venous return to the heart, thereby reducing left ventricular end- diastolic pressure and pulmonary capillary wedge pressure (preload). Arteriolar relaxation reduces systemic vascular resistance, systolic arterial pressure, and mean arterial pressure.
• Toxicity: Symptoms of overdose include reduced cardiac output and hypotension.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Absorption of isosorbide dinitrate after oral dosing is nearly complete, but bioavailability is highly variable (10% to 90%), with extensive first-pass metabolism in the liver. The average bioavailability of isosorbide dinitrate is about 25%.
• Half Life: 1 hour
• Protein Binding: Very low
• Distribution: * 2 to 4 L/kg
• External Links: RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - I901700

Coronary vasodilator.

REFERENCES

• Silvieri, L.A., et al.: Anal. Profiles Drug Subs., 4, 225 (1975)