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Triazoledione

From Wikipedia, the free encyclopedia
Phenylpiperazine compound
Pharmaceutical compound
Triazoledione
Clinical data
Other namesBMS-180492
Pharmacokinetic data
Eliminationhalf-life18 hours[1]
Identifiers
  • 1-[3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl]-4-(2-phenoxyethyl)-1,2,4-triazolidine-3,5-dione
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC23H28ClN5O3
Molar mass457.96 g·mol−1
3D model (JSmol)
  • C1CN(CCN1CCCN2C(=O)N(C(=O)N2)CCOC3=CC=CC=C3)C4=CC(=CC=C4)Cl
  • 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 nameBMS-180492) is aphenylpiperazinecompound and a majormetabolite of theantidepressantnefazodone.[2][3] It isactive, but with substantially reducedpotency 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]

Pharmacology

[edit]
Triazoledione[4][5][3]
SiteKi (nM)SpeciesRef
SERTTooltip Serotonin transporter≥34,527
≥26,471		Human
Rat		[5]
[5][3]
NETTooltip Norepinephrine transporter>100,000
100,000		Human
Rat		[5]
DATTooltip Dopamine transporterNDNDND
5-HT1A636–1,371Rat[3][5]
5-HT2A159–211Rat[5][3]
5-HT2CNDNDND
α1173
1,000		Human
Rat		[5]
[3]
α21,915
1,000		Human
Rat		[5]
[3]
β>100,000Rat[3]
H111Guinea pig[5]
mAChTooltip Muscarinic acetylcholine receptor>100,000Rat[5]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Triazoledione shows significantaffinity for theserotonin5-HT1A and5-HT2A receptors, theα1-adrenergic receptor, and thehistamineH1 receptor.[3][5] It shows negligible affinity for theserotonin andnorepinephrine transporters and themuscarinic acetylcholine receptors.[3][5]

Comparison of binding profiles of triazoledione and related compounds[3][5]
Compound5-HT1A5-HT2ASERTTooltip Serotonin transporterNETTooltip Norepinephrine transporterα1α2βH1mAChTooltip Muscarinic acetylcholine receptor
Hydroxynefazodone56–5897.2–34165–1,203376–1,0538.0–14563–2,490>1,0002811,357
mCPPTooltip meta-Chlorophenylpiperazine16–411110–433127–432490–4,36097–763112–3714,8904494,702
Nefazodone52–1,0307.1–32181–549200–7135.5–14484–41,700>100,000304,569
Trazodone42–28811–20115–690≥20,88712–23106–1,07047,1002912,188
Triazoledione636–1,371159–211≥26,471>100,000≥173≥1,915>100,00011>100,000
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

See also

[edit]

References

[edit]
  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.
  2. ^abcPreskorn 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.
  3. ^abcdefghijklmDavis 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.
  4. ^Roth BL, Driscol J."PDSP Ki Database".Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved14 August 2017.
  5. ^abcdefghijklmOwens MJ, Morgan WN, Plott SJ, Nemeroff CB (December 1997). "Neurotransmitter receptor and transporter binding profile of antidepressants and their metabolites".The Journal of Pharmacology and Experimental Therapeutics.283 (3):1305–1322.PMID 9400006.
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