CHEBI:32246 - tolvaptan

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ChEBI Name tolvaptan
ChEBI ID CHEBI:32246
Definition A benzazepine derivative incorporating a benzenedicarboxamide function whch is a selective vasopressin V2 receptor antagonist used to treat euvolemic and hypervolemic hyponatremia. It is also used in the treatment of rapidly progressing autosomal dominant polycystic kidney disease to slow the rate of cyst development and renal insufficiency. Tolvaptan is a racemate consisting of a 1:1 mixture of 5R and 5S stereomers.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C26H25ClN2O3
Net Charge 0
Average Mass 448.950
Monoisotopic Mass 448.15537
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)
InChIKey GYHCTFXIZSNGJT-UHFFFAOYSA-N
SMILES CC1=CC=CC=C1C(=O)NC1=CC(C)=C(C=C1)C(=O)N1CCCC(O)C2=CC(Cl)=CC=C12
Roles Classification
Biological Role(s): vasopressin receptor antagonist
Any drug which blocks vasopressin receptors.
Application(s): aquaretic
A class of diuretics which promote aquaresis (the excretion of water without electrolyte loss).
vasopressin receptor antagonist
Any drug which blocks vasopressin receptors.
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ChEBI Ontology
Outgoing tolvaptan (CHEBI:32246) has role aquaretic (CHEBI:194423)
tolvaptan (CHEBI:32246) has role vasopressin receptor antagonist (CHEBI:59680)
tolvaptan (CHEBI:32246) is a benzazepine (CHEBI:35676)
tolvaptan (CHEBI:32246) is a benzenedicarboxamide (CHEBI:38800)
Incoming DM-4103 (CHEBI:183655) has functional parent tolvaptan (CHEBI:32246)
DM-4107 (CHEBI:183656) has functional parent tolvaptan (CHEBI:32246)
IUPAC Name
N-[4-(7-chloro-5-hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide
INN Source
tolvaptan ChemIDplus
Synonyms Sources
jinarc DrugCentral
OPC 41061 DrugCentral
OPC-41061 DrugCentral
samsca DrugCentral
Tolvaptan KEGG COMPOUND
Manual Xrefs Databases
4110 DrugCentral
C12613 KEGG COMPOUND
D01213 KEGG DRUG
Tolvaptan Wikipedia
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Registry Numbers Types Sources
150683-30-0 CAS Registry Number KEGG COMPOUND
150683-30-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12742979 PubMed citation Europe PMC
16211205 PubMed citation Europe PMC
33078835 PubMed citation Europe PMC
34070416 PubMed citation Europe PMC
34386666 PubMed citation Europe PMC
34476570 PubMed citation Europe PMC
34514204 PubMed citation Europe PMC
34526469 PubMed citation Europe PMC
34554640 PubMed citation Europe PMC
Last Modified
20 February 2023