Etoperidone

In this article, we will explore the topic of Etoperidone in detail, analyzing its different aspects, impacts and perspectives. Etoperidone has been the subject of interest and controversy in recent times, and its relevance continues to grow in different areas. Throughout these pages, we will delve into its history, evolution and consequences, as well as the opinions and debates it has sparked. From a multidisciplinary approach, we will approach Etoperidone from various perspectives, trying to shed light on its implications and meanings. In short, this article aims to offer a broad and rigorous vision of Etoperidone, with the purpose of enriching knowledge and debate around this topic.

Etoperidone
Clinical data
Trade namesSeveral
Other namesST-1191; McN-A-2673-11
Routes of
administration		By mouth
ATC code
Identifiers
  • 2-propyl]-4,5-diethyl-1,2,4-triazol-3-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H28ClN5O
Molar mass377.92 g·mol−1
3D model (JSmol)
  • Clc3cccc(N2CCN(CCCN1/N=C(\N(C1=O)CC)CC)CC2)c3
  • InChI=1S/C19H28ClN5O/c1-3-18-21-25(19(26)24(18)4-2)10-6-9-22-11-13-23(14-12-22)17-8-5-7-16(20)15-17/h5,7-8,15H,3-4,6,9-14H2,1-2H3 checkY
  • Key:IZBNNCFOBMGTQX-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Etoperidone, associated with several brand names, is an atypical antidepressant which was developed in the 1970s and either is no longer marketed or was never marketed. It is a phenylpiperazine related to trazodone and nefazodone in chemical structure and is a serotonin antagonist and reuptake inhibitor (SARI) similarly to them.

Medical uses

Etoperidone was used or was intended for use as an antidepressant in the treatment of depression.

Pharmacology

Pharmacodynamics

Etoperidone
Site Ki (nM) Species Ref
SERTTooltip Serotonin transporter 890 Human
NETTooltip Norepinephrine transporter 20,000 Human
DATTooltip Dopamine transporter 52,000 Human
5-HT1A 85 Human
5-HT2A 36 Human
5-HT2C ? ? ?
α1 38 Human
α2 570 Human
D2 2,300 Human
H1 3,100 Human
mAChTooltip Muscarinic acetylcholine receptor >35,000 Human
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Etoperidone is as an antagonist of several receptors in the following order of potency: 5-HT2A receptor (36 nM) > α1-adrenergic receptor (38 nM) > 5-HT1A receptor (85 nM) (may be a partial agonist) > α2-adrenergic receptor (570 nM); it has only very weak or negligible affinity for blocking the following receptors: D2 receptor (2,300 nM) > H1 receptor (3,100 nM) > mACh receptors (>35,000 nM). In addition to its receptor blockade, etoperidone also has weak affinity for the monoamine transporters as well: serotonin transporter (890 nM) > norepinephrine transporter (20,000 nM) > dopamine transporter (52,000 nM).

Pharmacokinetics

Etoperidone is metabolized in part to meta-chlorophenylpiperazine (mCPP), which likely accounts for its serotonergic effects.

Chemistry

Etoperidone is a phenylpiperazine and is chemically related to nefazodone and trazodone.

History

Etoperidone was discovered by scientists at Angelini, who also discovered trazodone. Its development names have included ST-1191 and McN-A-2673-11. The INNTooltip International Nonproprietary Name etoperidone was proposed in 1976 and recommended in 1977. The drug was given brand names in Spain (Centren (Esteve) and Depraser (Lepori)) and Italy (Staff (Sigma Tau)) and was also given the brand names Axiomin and Etonin, but it is not entirely clear if it was actually marketed; the Pharmaceutical Manufacturing Encyclopedia provides no dates for commercial introduction. According to Micromedex's Index Nominum: International Drug Directory, etoperidone was indeed previously marketed in Spain and Italy.

Society and culture

Generic names

Etoperidone is the generic name of the drug and its INNTooltip International Nonproprietary Name, while etoperidone hydrochloride is its USANTooltip United States Adopted Name.

Brand names

Etoperidone has been associated with the brand names Axiomin, Centren, Depraser, Etonin, and Staff.

Research

Etoperidone has been studied in dementia and found to be about as effective as thioridazine.

See also

References

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  2. ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1533–. ISBN 978-0-8155-1856-3.
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  14. ^ Silvestrini B (1986). "Trazodone and the mental pain hypothesis of depression". Neuropsychobiology. 15 (Suppl 1): 2–9. doi:10.1159/000118270. PMID 3014372.
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  16. ^ "Proposed INN List 36" (PDF). Supplement to the WHO Chronicle. 30 (9). 1976.
  17. ^ "Recommended INN List 17" (PDF). Supplement to the WHO Chronicle. 31 (10). 1977.
  18. ^ a b McPherson EM (2007). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. p. 1533. ISBN 978-0-8155-1856-3.
  19. ^ Kirchner V, Kelly CA, Harvey RJ (2001). "Thioridazine for dementia". The Cochrane Database of Systematic Reviews (3): CD000464. doi:10.1002/14651858.CD000464. PMC 7034526. PMID 11686961.

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