Oxypertine

Oxypertine, sold under the brand name Oxypertine among others, is an antipsychotic medication of the tryptamine and phenylpiperazine groups which was previously used in the treatment of schizophrenia but is no longer marketed.^[2] It was also evaluated for the treatment of anxiety.^[3]

Oxypertine

Clinical data
Trade names	Oxypertine, others
Other names	WIN-18501; WIN18501; WIN-18,501, Win-18501; Win-18501-2
AHFS/Drugs.com	International Drug Names
Routes of administration	By mouth
ATC code	N05AE01 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1] In general: ℞ (Prescription only)
Identifiers
IUPAC name 5,6-Dimethoxy-2-methyl-3-[2-(4-phenylpiperazin-1-yl)ethyl]-1H-indole
CAS Number	153-87-7 Y
PubChem CID	4640
ChemSpider	4479 Y
UNII	5JGL4G25R7
KEGG	D01219 Y
CompTox Dashboard (EPA)	DTXSID20165185
ECHA InfoCard	100.005.291
Chemical and physical data
Formula	C23H29N3O2
Molar mass	379.504 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4
InChI InChI=1S/C23H29N3O2/c1-17-19(20-15-22(27-2)23(28-3)16-21(20)24-17)9-10-25-11-13-26(14-12-25)18-7-5-4-6-8-18/h4-8,15-16,24H,9-14H2,1-3H3 N Key:XCWPUUGSGHNIDZ-UHFFFAOYSA-N N
(verify)

Pharmacology

Pharmacodynamics

The drug shows high affinity for the serotonin 5-HT₂ and dopamine D₂ receptors (K_i = 8.6 nM and 30 nM, respectively).^[4] It antagonizes the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.^[4][5] Like reserpine and tetrabenazine, oxypertine depletes catecholamines, though not serotonin, possibly contributing to its antipsychotic effectiveness.^[6]

Chemistry

Chemically, it is a substituted tryptamine and phenylpiperazine derivative.^[7] Its chemical structure is similar to other "pertines" including alpertine, milipertine, and solypertine.^[8][9]

History

Oxypertine was first described in the scientific literature by 1962.^[10]

Society and culture

Names

Oxypertine is the generic name of the drug and its INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name, DCFTooltip Dénomination Commune Française, and JANTooltip Japanese Accepted Name.^{[10][11][12][13]} It is also known by its former developmental code name WIN-18501.^{[10][11][12][13]} The drug has been sold under brand names including Equipertine, Forit, Integrin, Lanturil, Lotawin, Opertil, and Oxypertine.^{[10][11][12][13]}

References

1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
2. Hall C, Rhodes PH (1996). Dictionary of organic compounds. London: Chapman & Hall. ISBN 0-412-54090-8.
3. Somohano MD, Broissin MC, Sobrino ZA (1976). "[Clinical evaluation of oxypertine in anxiety conditions]". Neurologia, Neurocirugia, Psiquiatria (in Spanish). 17 (3): 171–180. PMID 12484.
4. Megens AA, Kennis LE (1996). "Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent?". Progress in Medicinal Chemistry. 33: 185–232. doi:10.1016/s0079-6468(08)70306-0. ISBN 978-0-444-82310-6. PMID 8776944. {{cite journal}}: Cite journal requires |journal= (help)
5. Niemegeers CJ, Janssen PA (June 1979). "A systematic study of the pharmacological activities of dopamine antagonists". Life Sciences. 24 (24). Elsevier BV: 2201–2216. doi:10.1016/0024-3205(79)90096-1. PMID 388130.
6. Bak IJ, Hassler R, Kim JS (1969). "Differential monoamine depletion by oxypertine in nerve terminals. Granulated synaptic vesicles in relation to depletion of norepinephrine, dopamine and serotonin". Zeitschrift Fur Zellforschung und Mikroskopische Anatomie. 101 (3): 448–462. doi:10.1007/BF00335580. PMID 5362847. S2CID 32583722.
7. Breulet M, Labar P, Delree C, Collard J, Bobon J (February 1968). "[Oxypertine, peperazine derivative of tryptophan with neuroleptic and dynamogenic properties]". Acta Neurologica et Psychiatrica Belgica (in French). 68 (2): 116–127. PMID 4972600.
8. Ellis GP, Luscombe DK (1996). Progress in Medicinal Chemistry. Elsevier Science. p. 219. ISBN 978-0-08-086281-1. Retrieved 30 October 2024. Pertines (class 7; Table 5.12) The pertines oxypertine, solypertine, milipertine, and alpertine are piperazinylethylindoles.
9. Lednicer D, Mitscher LA (1980). The Organic Chemistry of Drug Synthesis, Volume 2. Organic Chemistry Series of Drug Synthesis. Wiley. pp. 341–343. ISBN 978-0-471-04392-8. Retrieved 30 October 2024.
10. Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 924. ISBN 978-1-4757-2085-3. Retrieved 2 November 2024.
11. Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 779. ISBN 978-3-88763-075-1. Retrieved 2 November 2024.
12. Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 212. ISBN 978-94-011-4439-1. Retrieved 2 November 2024.
13. "List of Antipsychotics". Archived from the original on 2016-03-03.