Compound

Triazoledione

Original Wikipedia articleen.wikipedia.org/wiki/Triazoledione revision used (24 October 2026)

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Part of the metabolic pathway of Nefazodone. See the timeline on the metabolic highway.

Overview

Triazoledione (developmental code name BMS-180492) is a phenylpiperazine compound and a major metabolite of the antidepressant nefazodone. It is active, but with substantially reduced potency compared to nefazodone (approximately one-seventh). As such, it has been suggested that it is unlikely that triazoledione contributes significantly to the pharmacology of nefazodone. However, triazoledione may reach concentrations as great as 10 times those of nefazodone, and hence could still be a significant contributor to its therapeutic effects.[1][2] WP

Pharmacology

Triazoledione shows significant affinity for the serotonin 5-HT1A and 5-HT2A receptors, the α₁-adrenergic receptor, and the histamine H₁ receptor. It shows negligible affinity for the serotonin and norepinephrine transporters and the muscarinic acetylcholine receptors.[2][3] WP⚠ A table follows this text in the source and is not copied here. Open the source to see it.

Chemistry

Formula: C23H28ClN5O3 PC
CAS number: 153707-88-1 PC
Molar mass (g/mol): 458.0 PC
IUPAC name (computed by PubChem): 1-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-4-(2-phenoxyethyl)-1,2,4-triazolidine-3,5-dione PC
SMILES: C1CN(CCN1CCCN2C(=O)N(C(=O)N2)CCOC3=CC=CC=C3)C4=CC(=CC=C4)Cl PC
InChIKey: BTNXVMLCKOPOEP-UHFFFAOYSA-N PC
PubChem CID: 9804174

Harm reduction information

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Sources

Other Preskorn SH, Catterson ML. Antidepressants: Past, Present and Future. 6 December 2012
Journal / agency Davis R, Whittington R, Bryson HM. Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. April 1997. doi:10.2165/00003495-199753040-00006 · PMID 9098663
Journal / agency Owens MJ, Morgan WN, Plott SJ, Nemeroff CB. Neurotransmitter receptor and transporter binding profile of antidepressants and their metabolites. The Journal of Pharmacology and Experimental Therapeutics. December 1997. PMID 9400006

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.