Oxypertine

Antipsychotic medication From Wikipedia, the free encyclopedia

Oxypertine, sold under the brand name Oxypertine among others, is an antipsychotic medication of the pertine group 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]

Trade namesOxypertine, others
Other namesWIN-18501; WIN18501; WIN-18,501, Win-18501; Win-18501-2
Quick facts Clinical data, Trade names ...
Oxypertine
Clinical data
Trade namesOxypertine, others
Other namesWIN-18501; WIN18501; WIN-18,501, Win-18501; Win-18501-2
AHFS/Drugs.comInternational Drug Names
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Identifiers
  • 5,6-Dimethoxy-2-methyl-3-[2-(4-phenylpiperazin-1-yl)ethyl]-1H-indole
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.005.291 Edit this at Wikidata
Chemical and physical data
FormulaC23H29N3O2
Molar mass379.504 g·mol−1
3D model (JSmol)
  • CC1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4
  • 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)
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Pharmacology

Pharmacodynamics

The drug shows high affinity for the serotonin 5-HT2 and dopamine D2 receptors (Ki = 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]

See also

References

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