tolvaptan   Click here for help

GtoPdb Ligand ID: 2226

Synonyms: OPC-41061 | Samsca®
Approved drug
tolvaptan is an approved drug (FDA and EMA (2009))
Compound class: Synthetic organic
Comment: Tolvaptan is a selective, competitive vasopressin receptor 2 (V2) antagonist.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 69.64
Molecular weight 448.16
XLogP 5.4
No. Lipinski's rules broken 1
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Canonical SMILES Clc1ccc2c(c1)C(O)CCCN2C(=O)c1ccc(cc1C)NC(=O)c1ccccc1C
Isomeric SMILES Clc1ccc2c(c1)C(O)CCCN2C(=O)c1ccc(cc1C)NC(=O)c1ccccc1C
InChI InChI=1S/C26H25ClN2O3/c1-16-6-3-4-7-20(16)25(31)28-19-10-11-21(17(2)14-19)26(32)29-13-5-8-24(30)22-15-18(27)9-12-23(22)29/h3-4,6-7,9-12,14-15,24,30H,5,8,13H2,1-2H3,(H,28,31)
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Summary of Clinical Use Click here for help
Approved to treat hyponatraemia (abnormally low levels of sodium in the blood). Hyponatraemia may be caused by excessive (inappropriate) production of vasopressin (aka antidiuretic hormone), leading to retention of water in the bloodstream, which has a diluting effect on blood sodium levels. The EMA expanded marketing approval to include treatment of genetically inherited autosomal dominant polycystic kidney disease (ADPKD) in mid-2015 under the brand name (Jynarc®). This is the first drug approved for this serious genetic kidney disease. The FDA followed in April 2018, approving the use of Jynarque® branded tolvaptan as a first-line treatment aimed at slowing down the decline in kidney function in adults at risk of rapidly progressing ADPKD.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Tolvaptan is a competitive antagonist of vasopressin receptor 2 (AVPR2). Antagonism of the effect of endogenous vasopressin leads to an increase in urine production, decreased water in the blood and an increased blood sodium level.
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