Opipramol

Opipramol
Clinical data
Trade namesInsidon, Pramolan, others
Other namesG-33040; RP-8307[1]
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)[2]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability94%[3]
Protein binding91%[3]
MetabolismCYP2D6-mediated[3]
Elimination half-life6–11 hours[3]
ExcretionUrine (70%), feces (10%)[3]
Identifiers
  • 4-[3-(5H-dibenz[b,f]azepin- 5-yl)propyl]-1-piperazinethanol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.687 Edit this at Wikidata
Chemical and physical data
FormulaC23H29N3O
Molar mass363.505 g·mol−1
3D model (JSmol)
  • OCCN1CCN(CC1)CCCN4c2ccccc2\C=C/c3ccccc34
  • InChI=1S/C23H29N3O/c27-19-18-25-16-14-24(15-17-25)12-5-13-26-22-8-3-1-6-20(22)10-11-21-7-2-4-9-23(21)26/h1-4,6-11,27H,5,12-19H2 checkY
  • Key:YNZFUWZUGRBMHL-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Opipramol, sold under the brand name Insidon among others, is an anxiolytic and tricyclic antidepressant that is used throughout Europe.[1][4][5][6][7] Despite chemically being a tricyclic dibenzazepine (iminostilbene) derivative similar to imipramine, opipramol is not a monoamine reuptake inhibitor like most other tricyclic antidepressants, and instead, uniquely among antidepressants, acts primarily as a SIGMAR1 agonist.[7] It was developed by Schindler and Blattner in 1961.[8]

  1. ^ a b Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  2. ^ 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.
  3. ^ a b c d e Cite error: The named reference Mohapatra_2013 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  6. ^ Möller HJ, Volz HP, Reimann IW, Stoll KD (February 2001). "Opipramol for the treatment of generalized anxiety disorder: a placebo-controlled trial including an alprazolam-treated group". Journal of Clinical Psychopharmacology. 21 (1): 59–65. doi:10.1097/00004714-200102000-00011. PMID 11199949. S2CID 27014778.
  7. ^ a b Müller WE, Siebert B, Holoubek G, Gentsch C (November 2004). "Neuropharmacology of the anxiolytic drug opipramol, a sigma site ligand". Pharmacopsychiatry. 37 (Suppl 3): S189–S197. doi:10.1055/s-2004-832677. PMID 15547785. S2CID 260238755.
  8. ^ Grosser HH, Ryan E (February 1965). "Drug Treatment of Anxiety: A Controlled Study of Opipramol and Chlordiazepoxide". The British Journal of Psychiatry. 111 (471): 134–141. doi:10.1192/bjp.111.471.134. PMID 14270525. S2CID 40241272.