Chemistry:Dibenzepin

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Short description: Chemical compound
Dibenzepin
Skeletal formula of dibenzepin
Space-filling model of the dibenzepin molecule
Clinical data
Trade namesNoveril, Anslopax, Deprex, Ecatril, Neodit, Victoril
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability25%
Protein binding80%
MetabolismHepatic
Elimination half-life5 hours
ExcretionUrine (80%), feces (20%)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC18H21N3O
Molar mass295.386 g·mol−1
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Dibenzepin, sold under the brand name Noveril among others, is a tricyclic antidepressant (TCA) used widely throughout Europe for the treatment of depression.[1][2][3] It has similar efficacy and effects relative to other TCAs like imipramine but with fewer side effects.[4][5][6][7]

Medical uses

Dibenzepin is used mainly in the treatment of major depressive disorder.

Like other TCAs, dibenzepin may have potential use in the treatment of chronic neuropathic pain.

Overdose

Main page: Medicine:Tricyclic antidepressant overdose

As TCAs have a relatively narrow therapeutic index, the likelihood of overdose (both accidental and intentional) is fairly high and should be considered carefully by the prescribing physician prior to patient use. Symptoms of overdose are similar to those of other TCAs, with cardiac toxicity (due to inhibition of sodium and calcium channels) generally occurring before the threshold for serotonin syndrome is reached. Due to this risk, TCAs are rarely selected as the first-line treatment for depression.

Pharmacology

Pharmacodynamics

Dibenzepin[8]
Site Ki (nM) Species Ref
SERT ND ND ND
NET ND ND [9]
5-HT1A >10,000 Rat [10]
5-HT2A ≥1,500 Rat [10]
5-HT2C ND ND ND
α1 >10,000 Rat [10]
α2 >10,000 Rat [10]
DA >10,000 Bovine [10]
H1 23 Human [11]
H2 1,950 Human [11]
H3 >100,000 Human [11]
H4 >100,000 Human [11]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Dibenzepin acts as a selective norepinephrine reuptake inhibitor (NRI), with similar potency to that of imipramine.[9] It is also a potent antihistamine.[10][11] The drug has weak or negligible effects on serotonin and dopamine reuptake.[12][13] Unlike many other TCAs, dibenzepin has no antiadrenergic (α1, α2), antiserotonergic (5-HT1A, 5-HT2A), or antidopaminergic effects and has few or no anticholinergic (mACh) effects.[10][14]

Pharmacokinetics

Therapeutic levels of dibenzepin are approximately 85 to 850 nM.[11] Its plasma protein binding is approximately 80%.[15]

History

Dibenzepin was first introduced, in Switzerland and West Germany, in 1965.[2] It was introduced in France in 1967, in Italy in 1968, in the United Kingdom in 1970, and in Japan in 1975.[2] It was also marketed in a number of other countries, including Portugal and Israel.[2]

Society and culture

Brand names

Dibenzepin is or was marketed mainly under the brand name Noveril.[2] It has also been marketed under a number of other brand names, including Ansiopax, Deprex, Ecatril, Neodit, and Victoril.[2]

References

  1. ↑ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0. https://books.google.com/books?id=5GpcTQD_L2oC&q=dibenzepin&pg=PA323. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 Pharmaceutical manufacturing encyclopedia. Park Ridge, N.J., U.S.A: Noyes Publications. 1988. ISBN 0-8155-1144-2. https://books.google.com/books?id=X2EyLsG4bcUC&q=dibenzepin&pg=PA470. 
  3. ↑ "[Results of using tricyclic antidepressive drugs in the treatment of endogenous depression (comparative analysis of 7 drugs)]" (in pl). Psychiatria Polska 25 (3–4): 13–8. 1991. PMID 1687987. 
  4. ↑ "Novartis (dibenzepin) - Prescribing Information". http://www.health.gov.il/units/pharmacy/trufot/alonim/2107.pdf. 
  5. ↑ Poisoning and Toxicology Handbook, Fourth Edition (Poisoning and Toxicology Handbook (Leiken & Paloucek's)). Informa Healthcare. 2007. ISBN 978-1-4200-4479-9. https://books.google.com/books?id=0Bw2UJTC_uMC&q=dibenzepin&pg=PA242. 
  6. ↑ "Dibenzepin and amitriptyline in depressive states: comparative double-blind trial". The New Zealand Medical Journal 83 (560): 194–7. March 1976. PMID 6928. 
  7. ↑ "A double blind study of the antidepressants dibenzepin (Noveril) and amitriptyline". The New Zealand Medical Journal 83 (562): 273–4. April 1976. PMID 8749. 
  8. ↑ "PDSP Ki Database". Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. https://kidbdev.med.unc.edu/databases/pdsp.php?knowID=0&kiKey=&receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=dibenzepin&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query. 
  9. ↑ 9.0 9.1 "Arrhythmias and inhibition of noradrenaline uptake caused by tricyclic antidepressants and chlorpromazine on the isolated perfused rabbit heart". Naunyn Schmiedebergs Arch. Pharmacol. 288 (2–3): 215–31. 1975. doi:10.1007/bf00500528. PMID 1161046. 
  10. ↑ 10.0 10.1 10.2 10.3 10.4 10.5 10.6 "Investigation of the influence of lithium upon the down-regulation of serotonin2 receptors in rat frontal cortex induced by long-term treatment with dibenzepin, an antidepressant without appreciable affinity to serotonin2 receptors". Naunyn Schmiedebergs Arch. Pharmacol. 326 (4): 291–3. 1984. doi:10.1007/bf00501432. PMID 6148707. 
  11. ↑ 11.0 11.1 11.2 11.3 11.4 11.5 "Interactions of recombinant human histamine H1R, H2R, H3R, and H4R receptors with 34 antidepressants and antipsychotics". Naunyn Schmiedebergs Arch. Pharmacol. 385 (2): 145–70. 2012. doi:10.1007/s00210-011-0704-0. PMID 22033803. 
  12. ↑ "Initial serotonin transport into viable platelets and imipramine binding to platelet membranes". J Neural Transm (Vienna) 109 (5–6): 547–56. 2002. doi:10.1007/s007020200045. PMID 12111448. 
  13. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named pmid656154
  14. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named pmid20647
  15. ↑ "Medikamente und andere Behandlungsverfahren". Psychiatrische Therapie. Schattauer Verlag. 2007. pp. 270–. ISBN 978-3-7945-2189-0. https://books.google.com/books?id=Ag8-W3IqG4wC&pg=PA270. 

External links



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