Tolvaptan Basic information

Description Synthesis Precautions References

Product Name: Tolvaptan

Synonyms: N-[4-(9-chloro-6-hydroxy-2-azabicyclo[5.4.0]undeca-8,10,12-triene-2-carbonyl)-3-methyl-phenyl]-2-methyl-benzamide;N-[4-[(5R)-7-Chloro-5-hydroxy-2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl]-3-methylphenyl]-2-methylbenzamide;Tolvaptan;OPC 41061;OPC-41061;SaMsca;Tolvaptan Tablets;N-(4-(7-Chloro-5-hydroxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-Methylphenyl)-2-MethylbenzaMide

CAS: 150683-30-0

MF: C26H25ClN2O3

MW: 448.94

EINECS:

Product Categories: APIs;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labelled Compounds;Tolvaptan;Samsca;Other APIs;Inhibitors

Mol File: 150683-30-0.mol

Tolvaptan Structure

Tolvaptan Chemical Properties

Melting point 219-222°C

storage temp. Refrigerator

solubility DMSO: ≥15mg/mL

color white to tan

Safety Information

MSDS Information

Tolvaptan Usage And Synthesis

Description Tolvaptan(trade names Samsca and Jinarc) is an oral selective vasopressin antagonist developed by Otsuka for the treatment of hyponatremia, and it is a non-peptide selective antidiuretic hormone receptor antagonist. The drug can increase the concentration of sodium ions in the plasma, and help the excess water discharge from the urine. The drug could enhance the ability of the kidney to deal with water, and significantly reduce the weight and edema of patients while not accompanied by increased electrolyte excretion, without destroying the blood electrolyte balance. The drug can be used to treat hyponatremia caused by congestive heart failure, various edematous diseases, cirrhosis and antidiuretic hormone deficiency syndrome. The study found that, when the plasma sodium concentration decreased, in order to maintain the balance of sodium concentration inside and outside the cell, extracellular fluid will enter the cell, so the cells will swell. When the brain cells swell, it will lead to a variety of hyponatremia symptoms, including dizziness, weakness, headache, nausea, confusion, consciousness and convulsions. Severe hyponatremia can lead to coma and death. There is no corresponding study of tolvaptan tablets in patients with severe hyponatremia.

Synthesis Synthesis of Tolvaptan

Fugure 1: Synthesis of Tolvaptan

Precautions Tolvaptan(SAMSCA) should be initiated and re-initiated in patients only in a hospital where serum sodium can be monitored closely. Too rapid correction of hyponatremia (e.g., >12 mEq/L/24 hours) can cause osmotic demyelination resulting in dysarthria, mutism, dysphagia, lethargy, affective changes, spastic quadriparesis, seizures, coma and death. In susceptible patients, including those with severe malnutrition, alcoholism or advanced liver disease, slower rates of correction may be advisable.

Tolvaptan(SAMSCA) is contraindicated in the following conditions:

 

Urgent need to raise serum sodium acutely

Inability of the patient to sense or appropriately respond to thirst

Hypovolemic hyponatremia

Concomitant use of strong CYP 3A inhibitors

Anuric patients

Hypersensitivity (e.g. anaphylactic shock, rash generalized) to tolvaptan or its components

References #

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Chemical Properties White Solid

Uses Tolvaptan (OPC-41061) is a selective, competitive arginine vasopressin receptor 2 antagonist with an IC50 of 1.28μM for the inhibition of AVP-induced platelet aggregation. Tolvaptan (OPC-41061) is used to treat hyponatremia (low blood sodium levels) assoc

Uses Labelled Tolvaptan s, and the syndrome of inappropriate antidiuretic hormone (SIADH).

Uses It is a selective, competitive arginine vasopressin V2 receptor antagonist f inappropriate antidiuretic hormone (SIADH).

Tolvaptan Preparation Products And Raw materials