Triazoledione

Triazoledione
Clinical data
Other names	BMS-180492
Pharmacokinetic data
Elimination half-life	18 hours
Identifiers
	IUPAC name 1-[3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl]-4-(2-phenoxyethyl)-1,2,4-triazolidine-3,5-dione;
CAS Number	153707-88-1;
PubChem CID	9804174;
ChemSpider	7979934;
UNII	3508097W2U;
ChEMBL	ChEMBL1598729;
CompTox Dashboard (EPA)	DTXSID701122505 ;
Chemical and physical data
Formula	C23H28ClN5O3
Molar mass	457.96 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCN1CCCN2C(=O)N(C(=O)N2)CCOC3=CC=CC=C3)C4=CC(=CC=C4)Cl;
	InChI InChI=1S/C23H28ClN5O3/c24-19-6-4-7-20(18-19)27-14-12-26(13-15-27)10-5-11-29-23(31)28(22(30)25-29)16-17-32-21-8-2-1-3-9-21/h1-4,6-9,18H,5,10-17H2,(H,25,30); Key:BTNXVMLCKOPOEP-UHFFFAOYSA-N;

Triazoledione (developmental code name BMS-180492) is a phenylpiperazine compound and a major metabolite of the antidepressant nefazodone.^[2]^[3] It is active, but with substantially reduced potency compared to nefazodone (approximately one-seventh).^[3]^[2] As such, it has been suggested that it is unlikely that triazoledione contributes significantly to the pharmacology of nefazodone.^[3] 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.^[2]

^ Golden RN, Dawkins K, Nicholas L (2017). "Trazodone and Nefazodone". In Schatzberg AF, Nemeroff CB (eds.). The American Psychiatric Association Publishing Textbook of Psychopharmacology (Fifth ed.). American Psychiatric Pub. pp. 460–. ISBN 978-1-58562-523-9.
^ ^a ^b ^c Preskorn SH, Catterson ML (6 December 2012). "General Principles of Pharmacokinetics". In Preskorn SH, Stanga CY, Feighner JP, Ross R (eds.). Antidepressants: Past, Present and Future. Springer Science & Business Media. pp. 68–. ISBN 978-3-642-18500-7.
^ ^a ^b ^c Davis R, Whittington R, Bryson HM (April 1997). "Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression". Drugs. 53 (4): 608–636. doi:10.2165/00003495-199753040-00006. PMID 9098663. S2CID 239077479.

[SchatzbergNemeroff2017-1] Golden RN, Dawkins K, Nicholas L (2017). "Trazodone and Nefazodone". In Schatzberg AF, Nemeroff CB (eds.). The American Psychiatric Association Publishing Textbook of Psychopharmacology (Fifth ed.). American Psychiatric Pub. pp. 460–. ISBN 978-1-58562-523-9.

[PreskornStanga2012-2] Preskorn SH, Catterson ML (6 December 2012). "General Principles of Pharmacokinetics". In Preskorn SH, Stanga CY, Feighner JP, Ross R (eds.). Antidepressants: Past, Present and Future. Springer Science & Business Media. pp. 68–. ISBN 978-3-642-18500-7.

[pmid9098663-3] Davis R, Whittington R, Bryson HM (April 1997). "Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression". Drugs. 53 (4): 608–636. doi:10.2165/00003495-199753040-00006. PMID 9098663. S2CID 239077479.

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