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Your Location：Home>Product Center >> Pharmaceutical API >> Isosorbide dinitrate
  • Isosorbide dinitrate
Name:Isosorbide dinitrate
CAS No:87-33-2

PRODUCT DESCRIPTION

【Name】
isosorbide dinitrate
【CAS Registry number】
87-33-2
【Synonyms】
1,4:3,6-dianhydrosorbitol 2,5-dinitrate
sorbide nitrate
Isosobide dinitrate
【EINECS(EC#)】
201-740-9
【Molecular Formula】
C6H8N2O8 (Products with the same molecular formula)
【Molecular Weight】
236.14
【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
【Canonical SMILES】
C1C(C2C(O1)C(CO2)O[N+](=O)[O-])O[N+](=O)[O-]
【Isomers smiles】
C1[C@H]([C@@H]2[C@H](O1)[C@H](CO2)O[N+](=O)[O-])O[N+](=O)[O-]
【MOL File】
87-33-2.mol

Chemical and Physical Properties

【Appearance】
white crystalline powder
【Density】
1.65g/cm3
【Melting Point】
69 C
【Boiling Point】
365.9°C at 760 mmHg
【Refractive Index】
1.537
【Flash Point】
186.6°C
【Solubilities】
Insoluble
【Color/Form】
Hard, colorless crystals
DILUTED: IVORY-WHITE, POWDER; UNDILUTED: WHITE, CRYSTALLINE ROSETTES
【Stability】
No data.
【Storage temp】
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
【Spectral properties】
Specific optical rotation: +135 deg @ 20 deg C/D (alcohol, 1%)
【Computed Properties】
Molecular Weight:236.13632 [g/mol]
Molecular Formula:C6H8N2O8
XLogP3:1.3
H-Bond Donor:0
H-Bond Acceptor:8
Rotatable Bond Count:2
Exact Mass:236.028065
MonoIsotopic Mass:236.028065
Topological Polar Surface Area:129
Heavy Atom Count:16
Formal Charge:0
Complexity:268
Isotope Atom Count:0
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:6
Feature 3D Ring Count:2
Effective Rotor Count:5.2
Conformer Sampling RMSD:0.6
CID Conformer Count:22

Safety and Handling

【Hazard Codes】
Xn:Harmful;
【Risk Statements】
R5;R22
【Safety Statements 】
S36
【HazardClass】
1.1A
【Safety】

Moderately toxic by ingestion, intraperitoneal, intramuscular, and subcutaneous routes. Experimental reproductive effects. Mutation data reported. A flammable solid. When heated to decomposition it emits toxic fumes of NOx. A coronary vasodilator. 
Hazard Codes: HarmfulXn
Risk Statements: 5-22
R5 :Heating may cause an explosion. 
R22:Harmful if swallowed. 
Safety Statements: 36 
S36:Wear suitable protective clothing. 
RIDADR: UN 2907 
HazardClass: 1.1A 
PackingGroup: II

【PackingGroup 】
II
【Transport】
UN 2907
【Formulations/Preparations】
SUBLINGUAL TABLETS: 2.5, 5 MG; CHEWABLE ORAL TABLETS: 5, 10 MG; ORAL TABLETS: 5, 10, 20 MG; TIME-RELEASE TABLETS: 40 MG. /FROM TABLE/
Sorbitrate 5, 10, 20, 40 mg tablets
Isordil titradose 5, 10, 20, 30, 40 mg tablets
Dilatrate-SR 40 mg capsules, extended release
Trade Names: Isoket (Pharma-Schwarz, Iso Mack (Mack), Isordril (Wyeth), Sorbitrate (Stuart).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl isosorbide dinitrate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Drug preparations intended for human use containing certain "coronary vasodilators". The Food and Drug Administraton finds that the following "coronary vasodilators" are extensively regarded by physicians as safe and useful as employed under medical supervision for the management of angina pectoris in some patients. Isosorbide dinitrate is included on this list.
【Reactivities and Incompatibilities】
Exptl studies were carried out on pure isosorbide dinitrate and its mixture with lactose to investigate thermal stability, impact and friction sensitivities, and sensitivity to initiation to detonation by std no. 6 and no. 8 strength detonators; compounds had low hazard potential.
【Specification】

  Cardis (CAS NO.87-33-2), its Synonyms are Isosorbide dinitrate ; 1,4:3,6-Dianhydro-D-glucitol dinitrate ; 1,4:3,6-Dianhydrosorbitol 2,5-dinitrate ; Angidil ; Astridine ; Corosorbide ; Corovliss ; D-Isosorbide dinitrate ; Dianhydrosorbitol 2,5-dinitrate ; D-Glucitol, 1,4:3,6-dianhydro-, 2,5-dinitrate ; D-Glucitol, 1,4:3,6-dianhydro-, dinitrate ; Glucitol, 1,4:3,6-dianhydro-, dinitrate, D- . It is crystalline solid. May be toxic by ingestion.

【Octanol/Water Partition Coefficient】
log Kow = 1.31
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

PREPARATION FROM SORBITAL
【Usage】
Coronary vasodilator

Biomedical Effects and Toxicity

【Pharmacological Action】
- A diverse group of agents, with unique chemical structures and biochemical requirements, which generate NITRIC OXIDE. These compounds have been used in the treatment of cardiovascular diseases and the management of acute myocardial infarction, acute and chronic congestive heart failure, and surgical control of blood pressure. (Adv Pharmacol 1995;34:361-81)
- Drugs used to cause dilation of the blood vessels.
【Therapeutic Uses】
Vasodilator Agents
In a limited number of patients with diffuse esophageal spasm without gastroesophageal reflux, isosorbide dinitrate has been used effectively to relieve pain, dysphagia and spasm.
Isosorbide dinitrate (in combination with cardiac glycosides and diuretics or with hydralazine) has been used effectively for the treatment of congestive heart failure or other low cardiac output states.
...Isosorbide dinitrate shares the actions of the other nitrates and nitrites. The drug is used for the acute relief of angina pectoris, for prophylactic management in situations likely to provoke angina attacks, and for long term prophylactic management of angina pectoris.
Antianginal or cardiac load-reducing agent... thought to cause a reduction of myocardial oxygen demand. this is attributed to a reduction in left ventricular preload and afterload because of venous and aterial dilation with a more efficient redistribution of blood flow within the myocardium. /nitrates/
/EXPTL THER/ ...Isosorbide dinitrate, Isoket spray (Schwarz-Pharma, Mannheim, Germany), was used to treat 41 patients with chronic anal fissure. Anal manometry was performed in all patients before they entered the study. The treatment program consisted of digital application of isosorbide dinitrate in a dose of 1.25 mg or 2.5 mg three times each day for 4 wk. At the end of the trial, patients were followed up for an avg time of 11 +/- 1 months. In 34 (83%) patients, the fissure healed within 1 month of treatment (mean, 3 +/- 0.1 weeks). The avg time for symptoms to disappear was 6.5 +/- 0.7 days. In 6 (14.6%) patients the anal fissure did not heal even after 4 wk of further treatment, and they underwent lateral sphincterotomy. Six patients relapsed during the follow-up period, but responded to another course of treatment. A dose of 2.5 mg of isosorbide dinitrate caused a greater reduction in max anal resting pressure than a dose of 1.25 mg. ... [Lysy J et al; Dis Colon Rectum 41 (11): 1406-10 (1998)]
【Biomedical Effects and Toxicity】
After sublingual admin, onset of effect is 2-3 min & offset of effect is about 2 hr.
Following sublingual doses of 5 mg, oral conventional tablets of 5 mg, and oral sustained-release tablets of 20 mg, mean peak isosorbide dinitrate levels of 8.9, 3.1, and 1.4 ng/ml, occurred at 30, 40, and 40 min respectively. Plasma levels...after sustained-release dosage...maintained above half of mean peak level for 10 hours.
Chronic oral administration of isosorbide dinitrate (120 to 720 mg daily) has resulted in persistence of parent compound and higher concentration of metabolite in plasma.
Since denitration markedly reduces activity of organic nitrates, their rapid clearance from blood indicates that transient duration of action under these conditions correlates with concentration of parent compounds. /organic nitrates/
Levels of (14)C in plasma of dogs were maximal within 15 min of iv injection of (14)C isosorbide dinitrate and within 2 hr after oral dose, declining rapidly to negligible levels after 24 hr.
18 subjects were given 5 mg isosorbide dinitrate sublingually. It was rapidly absorbed and metabolized with elimination t/2 of 29 min. Amplitude of alpha-wave of digital plethysmograph increased within 4 min of administration and reached max after 14 min.
When (14)C-labelled isosorbide dinitrate was cutaneously applied in an ointment base, 90, 30, and 10-15% of the radioactivity was absorbed by rabbits, rats, and humans, respectively.
Plasma concentrations of isosorbide dinitrate were measured after iv infusion of drug at 5.0 mg/hr for 150 min to 2 human subjects. Avg steady-state plasma levels were 258 ng/ml and 514 ng/ml, respectively. T/2 of elimination after end of infusion was 9-10 min.
Isosorbide dinitrate is readily (and almost completely) absorbed from the gastrointestinal tract and oral mucosa, but considerable variations in the bioavailability of the drug (10-90%) have been reported as a result of extensive first-pass metabolism in the liver. The bioavailability of isosorbide dinitrate, as unchanged drug, following oral administration of conventional tablets (25%) generally appears to be about half that following sublingual administration (40-50%).
Once absorbed, isosorbide dinitrate is widely distributed into body tissues and fluids including smooth muscle cells of blood vessels with an apparent volume of distribution reported to be 2-4 l/kg in adults. ... Isosorbide dinitrate /is/... approximately 28% ...bound to plasma proteins... .
After a single oral dose of isosorbide dinitrate, 80 to 100% of the amount is excreted in urine within 24 hours, chiefly as metabolites.
After oral admin of ISMN as a soln or immediate-release tablets, max plasma concns of ISMN are achieved in 30-60 min, with an absolute bioavailability of approx 100%. After iv admin, ISMN is distributed into total body water in about 9 min with a volume of distribution of approx 0.6-0.7 l/kg. Isosorbide mononitrate is approx 5% bound to human plasma proteins and is distributed into blood cells and saliva. ...At least 6 different compounds have been detected in urine, with about 2% of the dose excreted as the unchanged drug and at least five metabolites. The metabolites are not pharmacologically active. Renal clearance accounts for only about 4% of total body clearance. /Isosorbide mononitrate/
The plasma clearence of isosorbide dinitrate reportedly is 2-4 l/min. Since plasma clearance exceeds hepatic blood flow, it appears that the drug also is metabolized at extrahepatic sites.

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