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Etoperidone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Etoperidone
Clinical data
Trade namesSeveral
Other namesST-1191; McN-A-2673-11
Routes of
administration		By mouth
ATC code
Identifiers
  • 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-4,5-diethyl-1,2,4-triazol-3-one
CAS Number
PubChemCID
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 anatypical antidepressant which was developed in the 1970s and either is no longer marketed or was never marketed.[1][2][3] It is aphenylpiperazine related totrazodone andnefazodone inchemical structure and is aserotonin antagonist and reuptake inhibitor (SARI) similarly to them.[4]

Medical uses

[edit]

Etoperidone was used or was intended for use as an antidepressant in the treatment ofdepression.[1][5]

Etoperidone might be useful as ahallucinogen antidote or "trip killer" in blocking the effects ofserotonergic psychedelics likepsilocybin andlysergic acid diethylamide (LSD).[6]

Pharmacology

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Pharmacodynamics

[edit]
Etoperidone[7]
SiteKi (nM)SpeciesRef
SERTTooltip Serotonin transporter890Human[8]
NETTooltip Norepinephrine transporter20,000Human[8]
DATTooltip Dopamine transporter52,000Human[8]
5-HT1A85Human[9]
5-HT2A36Human[9]
5-HT2C???
α138Human[9]
α2570Human[9]
D22,300Human[9]
H13,100Human[9]
mAChTooltip Muscarinic acetylcholine receptor>35,000Human[9][10]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Etoperidone is as anantagonist of severalreceptors in the following order ofpotency:5-HT2A receptor (36 nM) >α1-adrenergic receptor (38 nM) >5-HT1A receptor (85 nM) (may be apartial agonist) >α2-adrenergic receptor (570 nM);[9] it has only very weak or negligibleaffinity for blocking the following receptors:D2 receptor (2,300 nM) >H1 receptor (3,100 nM) >mACh receptors (>35,000 nM).[9] In addition to its receptor blockade, etoperidone also has weak affinity for themonoaminetransporters as well:serotonin transporter (890 nM) >norepinephrine transporter (20,000 nM) >dopamine transporter (52,000 nM).[8]

Pharmacokinetics

[edit]

Etoperidone ismetabolized in part tometa-chlorophenylpiperazine (mCPP), which likely accounts for itsserotonergic effects.[11][12]

Chemistry

[edit]

Etoperidone is aphenylpiperazine and is chemically related tonefazodone andtrazodone.[3][13][14]

History

[edit]

Etoperidone was discovered by scientists atAngelini, who also discovered trazodone.[15] Its development names have included ST-1191 and McN-A-2673-11.[16][1] TheINNTooltip International Nonproprietary Nameetoperidone was proposed in 1976 and recommended in 1977.[17][18] The drug was given brand names inSpain (Centren (Esteve) and Depraser (Lepori)) andItaly (Staff (Sigma Tau))[1] and was also given the brand names Axiomin and Etonin,[16] but it is not entirely clear if it was actually marketed; the Pharmaceutical Manufacturing Encyclopedia provides no dates for commercial introduction.[19] According toMicromedex's Index Nominum: International Drug Directory, etoperidone was indeed previously marketed in Spain and Italy.[1]

Society and culture

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Generic names

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Etoperidone is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name, whileetoperidone hydrochloride is itsUSANTooltip United States Adopted Name.[16][1][5]

Brand names

[edit]

Etoperidone has been associated with the brand names Axiomin, Centren, Depraser, Etonin, and Staff.[1][16][19]

Research

[edit]

Etoperidone has been studied indementia and found to be about as effective asthioridazine.[20]

See also

[edit]

References

[edit]
  1. ^abcdefgIndex Nominum 2000: International Drug Directory. Taylor & Francis. 2000. p. 421.ISBN 978-3-88763-075-1.
  2. ^William Andrew Publishing (22 October 2013).Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1533–.ISBN 978-0-8155-1856-3.
  3. ^abAkritopoulou-Zanze I (16 August 2012)."Arylpiperazine-Based 5-HT1A Receptor Partial Agonists and 5-HT2A Antagonists for the Treatment of Autism, Depression, Anxiety, Psychosis, and Schizophrenia". In Lamberth C, Dinges J (eds.).Bioactive Heterocyclic Compound Classes: Pharmaceuticals. John Wiley & Sons. pp. 81–97.doi:10.1002/9783527664450.ch6.ISBN 978-3-527-66447-4.
  4. ^Morrison-Valfre M (23 August 2016).Foundations of Mental Health Care - E-Book. Elsevier Health Sciences. pp. 245–.ISBN 978-0-323-37104-9.
  5. ^abMorton IK, Hall JM (6 December 2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 117–.ISBN 978-94-011-4439-1.
  6. ^Halman A, Kong G, Sarris J, Perkins D (January 2024)."Drug-drug interactions involving classic psychedelics: A systematic review".J Psychopharmacol.38 (1):3–18.doi:10.1177/02698811231211219.PMC 10851641.PMID 37982394.
  7. ^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.
  8. ^abcdTatsumi M, Groshan K, Blakely RD, Richelson E (1997). "Pharmacological profile of antidepressants and related compounds at human monoamine transporters".Eur. J. Pharmacol.340 (2–3):249–58.doi:10.1016/s0014-2999(97)01393-9.PMID 9537821.
  9. ^abcdefghiCusack B, Nelson A, Richelson E (1994). "Binding of antidepressants to human brain receptors: focus on newer generation compounds".Psychopharmacology.114 (4):559–65.doi:10.1007/bf02244985.PMID 7855217.S2CID 21236268.
  10. ^Stanton T, Bolden-Watson C, Cusack B, Richelson E (1993). "Antagonism of the five cloned human muscarinic cholinergic receptors expressed in CHO-K1 cells by antidepressants and antihistaminics".Biochem. Pharmacol.45 (11):2352–4.doi:10.1016/0006-2952(93)90211-e.PMID 8100134.
  11. ^Garattini S (1985). "Active drug metabolites. An overview of their relevance in clinical pharmacokinetics".Clinical Pharmacokinetics.10 (3):216–227.doi:10.2165/00003088-198510030-00002.PMID 2861928.S2CID 21305772.
  12. ^Raffa RB, Shank RP, Vaught JL (1992). "Etoperidone, trazodone and MCPP: in vitro and in vivo identification of serotonin 5-HT1A (antagonistic) activity".Psychopharmacology.108 (3):320–326.doi:10.1007/BF02245118.PMID 1387963.S2CID 24965789.
  13. ^Dörwald FZ, ed. (2012). "46. Arylalkylamines".Lead optimization for medicinal chemists: pharmacokinetic properties of functional groups and organic compounds. Weinheim: Wiley-VCH.ISBN 978-3-527-64564-0.
  14. ^Eison MS, Taylor DB, Riblet LA (1987)."Atypical Psychotropic Agents". In Williams M, Malick JB (eds.).Drug Discovery and Development. Springer Science & Business Media. p. 390.ISBN 978-1-4612-4828-6.
  15. ^Silvestrini B (1986). "Trazodone and the mental pain hypothesis of depression".Neuropsychobiology.15 (Suppl 1):2–9.doi:10.1159/000118270.PMID 3014372.
  16. ^abcdElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 527–.ISBN 978-1-4757-2085-3.
  17. ^"Proposed INN List 36"(PDF).Supplement to the WHO Chronicle.30 (9). 1976.
  18. ^"Recommended INN List 17"(PDF).Supplement to the WHO Chronicle.31 (10). 1977.
  19. ^abMcPherson EM (2007).Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. p. 1533.ISBN 978-0-8155-1856-3.
  20. ^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.

External links

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SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
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NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
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SMSTooltip Serotonin modulator and stimulators
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DATTooltip Dopamine transporter
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NETTooltip Norepinephrine transporter
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SERTTooltip Serotonin transporter
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VMATsTooltip Vesicular monoamine transporters
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