Dibenzepin

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Dibenzepin
Skeletal formula of dibenzepin
Space-filling model of the dibenzepin molecule
Clinical data
Trade names Noveril, Anslopax, Deprex, Ecatril, Neodit, Victoril
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 25%
Protein binding 80%
Metabolism Hepatic
Biological half-life 5 hours
Excretion Urine (80%), feces (20%)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
Formula C18H21N3O
Molar mass 295.379 g/mol
3D model (JSmol)
 NYesY (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[edit]

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[edit]

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[edit]

Pharmacodynamics[edit]

Dibenzepin[8]
Site Ki (nM) Species Ref
SERT ND ND ND
NET ND ND [9]
DAT >100,000 Rat [10]
5-HT1A >10,000 Rat [11]
5-HT2A ≥1,500 Rat [11]
5-HT2C ND ND ND
α1 >10,000 Rat [11]
α2 >10,000 Rat [11]
DA >10,000 Bovine [11]
H1 23 Human [12]
H2 1,950 Human [12]
H3 >100,000 Human [12]
H4 >100,000 Human [12]
mACh 1,750 Rat [11][13]
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.[11][12] The drug has weak or negligible effects on serotonin and dopamine reuptake.[14][10] 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.[11][13]

Pharmacokinetics[edit]

Therapeutic levels of dibenzepin are approximately 85 to 850 nM.[12] Its plasma protein binding is approximately 80%.[15]

History[edit]

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[edit]

Brand names[edit]

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[edit]

  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. 
  2. ^ a b c d e f Sittig, Marshall (1988). Pharmaceutical manufacturing encyclopedia. Park Ridge, N.J., U.S.A: Noyes Publications. ISBN 0-8155-1144-2. 
  3. ^ Beresewicz M, Bidzińska E, Koszewska I, Puzyński S (1991). "[Results of using tricyclic antidepressive drugs in the treatment of endogenous depression (comparative analysis of 7 drugs)]". Psychiatria Polska (in Polish). 25 (3-4): 13–8. PMID 1687987. 
  4. ^ "Novartis (dibenzepin) - Prescribing Information" (PDF). 
  5. ^ Paloucek, Frank P.; Leikin, Jerrold B. (2007). Poisoning and Toxicology Handbook, Fourth Edition (Poisoning and Toxicology Handbook (Leiken & Paloucek's)). Informa Healthcare. ISBN 1-4200-4479-6. 
  6. ^ Gowardman M, Brown RA (March 1976). "Dibenzepin and amitriptyline in depressive states: comparative double-blind trial". The New Zealand Medical Journal. 83 (560): 194–7. PMID 6928. 
  7. ^ Baron DP, Unger HR, Williams HE, Knight RG (April 1976). "A double blind study of the antidepressants dibenzepin (Noveril) and amitriptyline". The New Zealand Medical Journal. 83 (562): 273–4. PMID 8749. 
  8. ^ 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. Retrieved 14 August 2017. 
  9. ^ a b Barth N, Manns M, Muscholl E (1975). "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. PMID 1161046. 
  10. ^ a b Hyttel J (1978). "Inhibition of [3H]dopamine accumulation in rat striatal synaptosomes by psychotropic drugs". Biochem. Pharmacol. 27 (7): 1063–8. PMID 656154. 
  11. ^ a b c d e f g h Closse A, Jaton AL (1984). "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. PMID 6148707. 
  12. ^ a b c d e f Appl H, Holzammer T, Dove S, Haen E, Strasser A, Seifert R (2012). "Interactions of recombinant human histamine H₁R, H₂R, H₃R, and H₄R receptors with 34 antidepressants and antipsychotics". Naunyn Schmiedebergs Arch. Pharmacol. 385 (2): 145–70. doi:10.1007/s00210-011-0704-0. PMID 22033803. 
  13. ^ a b Rehavi M, Maayani S, Goldstein L, Assael M, Sokolovsky M (1977). "Antimuscarinic properties of antidepressants: dibenzepin (Noveril)". Psychopharmacology. 54 (1): 35–8. PMID 20647. 
  14. ^ Rao ML, Frahnert C, Zagorski O (2002). "Initial serotonin transport into viable platelets and imipramine binding to platelet membranes". J Neural Transm (Vienna). 109 (5-6): 547–56. doi:10.1007/s007020200045. PMID 12111448. 
  15. ^ Josef Aldenhoff (2007). Psychiatrische Therapie. Schattauer Verlag. pp. 270–. ISBN 978-3-7945-2189-0. 

External links[edit]