Triazoledione

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Triazoledione
File:Triazoledione.svg
Clinical data
Other namesBMS-180492
Pharmacokinetic data
Elimination half-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
PubChem CID
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
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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 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]

Pharmacology

[edit | edit source]
Triazoledione[4][5][3]
Site Ki (nM) Species Ref
SERTTooltip Serotonin transporter ≥34,527
≥26,471		 Human
Rat		 [5]
[5][3]
NETTooltip Norepinephrine transporter >100,000
100,000		 Human
Rat		 [5]
DATTooltip Dopamine transporter ND ND ND
5-HT1A 636–1,371 Rat [3][5]
5-HT2A 159–211 Rat [5][3]
5-HT2C ND ND ND
α1 173
1,000		 Human
Rat		 [5]
[3]
α2 1,915
1,000		 Human
Rat		 [5]
[3]
β >100,000 Rat [3]
H1 11 Guinea pig [5]
mAChTooltip Muscarinic acetylcholine receptor >100,000 Rat [5]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Triazoledione shows significant affinity for the serotonin 5-HT1A and 5-HT2A receptors, the α1-adrenergic receptor, and the histamine H1 receptor.[3][5] It shows negligible affinity for the serotonin and norepinephrine transporters and the muscarinic acetylcholine receptors.[3][5]

Comparison of binding profiles of triazoledione and related compounds[3][5]
Compound 5-HT1A 5-HT2A SERTTooltip Serotonin transporter NETTooltip Norepinephrine transporter α1 α2 β H1 mAChTooltip Muscarinic acetylcholine receptor
Hydroxynefazodone 56–589 7.2–34 165–1,203 376–1,053 8.0–145 63–2,490 >1,000 28 11,357
mCPPTooltip meta-Chlorophenylpiperazine 16–411 110–433 127–432 490–4,360 97–763 112–371 4,890 449 4,702
Nefazodone 52–1,030 7.1–32 181–549 200–713 5.5–144 84–41,700 >100,000 30 4,569
Trazodone 42–288 11–20 115–690 ≥20,887 12–23 106–1,070 47,100 29 12,188
Triazoledione 636–1,371 159–211 ≥26,471 >100,000 ≥173 ≥1,915 >100,000 11 >100,000
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

See also

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References

[edit | edit source]
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  2. ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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