Dibenzepin

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Dibenzepin
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	N06AA08 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	25% (Oral)
Protein binding	80%
Metabolism	Hepatic
Elimination half-life	5 hours
Excretion	Urine (80%), Feces (20%)
Identifiers
	IUPAC name 10-(2-(dimethylamino)ethyl)-5-methyl-5H-dibenzo[b,e][1,4]diazepin-11(10H)-one;
CAS Number	4498-32-2 ;
PubChem CID	9419;
ChemSpider	9048 ;
UNII	510SJZ1Y6L;
KEGG	D07812 ;
ChEMBL	ChEMBL1442422 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C18H21N3O
Molar mass	295.379 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C2c1c(cccc1)N(c3c(N2CCN(C)C)cccc3)C;
	InChI InChI=1S/C18H21N3O/c1-19(2)12-13-21-17-11-7-6-10-16(17)20(3)15-9-5-4-8-14(15)18(21)22/h4-11H,12-13H2,1-3H3 ; Key:QPGGEKPRGVJKQB-UHFFFAOYSA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Dibenzepin (Noveril, Anslopax, Deprex, Ecatril, Neodit, Victoril) 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] Dibenzepin acts as a norepinephrine reuptake inhibitor, potent antihistamine, and weak anticholinergic.^[4]^[5]^[8] It lacks any 5-HT₂ antagonistic properties.^[9]

Chronic Pain

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

Overdose

As tricyclic antidepressants 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 tricyclic antidepressants, 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, tricyclic antidepressants are rarely selected as the first line treatment for depression.

Synthesis

The Ullmann reaction provides the key for preparing the diaryl-amine or -ether starting materials in this series.

Copper catalyzed coupling of methyl N-methylanthranilate () with nitrobromobenzene () leads to the arylaniline (). The ester is then saponified () and the nitro group reduced to the corresponding amine (). That product cyclizes to the lactam () on heating. A strong base preferentially removes the proton on the lactam nitrogen to form an anion. Alkylation with 2-chloroethyldimethylamine then affords dibenzepin (), a compound that shows antidepressant activity.^[11]

References

↑ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.
↑ Sittig, Marshall (1988). Pharmaceutical manufacturing encyclopedia. Park Ridge, N.J., U.S.A: Noyes Publications. ISBN 0-8155-1144-2.
↑ 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.
↑ ^4.0 ^4.1 "Novartis (dibenzepin) - Prescribing Information" (PDF).
↑ ^5.0 ^5.1 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.
↑ 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.
↑ 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.
↑ Rehavi M, Maayani S, Goldstein L, Assael M, Sokolovsky M (August 1977). "Antimuscarinic properties of antidepressants: dibenzepin (Noveril)". Psychopharmacology. 54 (1): 35–8. doi:10.1007/BF00426538. PMID 20647.
↑ Closse A, Jaton AL (July 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-Schmiedeberg's Archives of Pharmacology. 326 (4): 291–3. doi:10.1007/bf00501432. PMID 6148707.
↑ Hunziker, F.; Lauener, H.; Schmutz, J.; Arzneim. Forsch. 1963, 13, 324.
↑ Hunziker, F.; Lauener, H.; Schmutz, J.; Arzneim. Forsch. 1963, 13, 324.

External links

"Novartis - Noveral (dibenzepin) - Prescribing Information" (PDF).

Template:Antidepressants

[isbn3-88763-075-0-1] Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.

[isbn0-8155-1144-2-2] Sittig, Marshall (1988). Pharmaceutical manufacturing encyclopedia. Park Ridge, N.J., U.S.A: Noyes Publications. ISBN 0-8155-1144-2.

[pmid1687987-3] 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.

[urlwww.health.gov.il-4] 4.0 ^4.1 "Novartis (dibenzepin) - Prescribing Information" (PDF).

[isbn1-4200-4479-6-5] 5.0 ^5.1 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.

[pmid6928-6] 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.

[pmid8749-7] 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.

[pmid20647-8] Rehavi M, Maayani S, Goldstein L, Assael M, Sokolovsky M (August 1977). "Antimuscarinic properties of antidepressants: dibenzepin (Noveril)". Psychopharmacology. 54 (1): 35–8. doi:10.1007/BF00426538. PMID 20647.

[pmid6148707-9] Closse A, Jaton AL (July 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-Schmiedeberg's Archives of Pharmacology. 326 (4): 291–3. doi:10.1007/bf00501432. PMID 6148707.

[10] Hunziker, F.; Lauener, H.; Schmutz, J.; Arzneim. Forsch. 1963, 13, 324.

[11] Hunziker, F.; Lauener, H.; Schmutz, J.; Arzneim. Forsch. 1963, 13, 324.

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Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	N06AA08 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	25% (Oral)
Protein binding	80%
Metabolism	Hepatic
Elimination half-life	5 hours
Excretion	Urine (80%), Feces (20%)
Identifiers
IUPAC name 10-(2-(dimethylamino)ethyl)-5-methyl-5H-dibenzo[b,e][1,4]diazepin-11(10H)-one
CAS Number	4498-32-2^Y
PubChem CID	9419
ChemSpider	9048^Y
UNII	510SJZ1Y6L
KEGG	D07812^Y
ChEMBL	ChEMBL1442422^N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₁₈H₂₁N₃O
Molar mass	295.379 g/mol
3D model (JSmol)	Interactive image
SMILES O=C2c1c(cccc1)N(c3c(N2CCN(C)C)cccc3)C
InChI InChI=1S/C18H21N3O/c1-19(2)12-13-21-17-11-7-6-10-16(17)20(3)15-9-5-4-8-14(15)18(21)22/h4-11H,12-13H2,1-3H3^Y Key:QPGGEKPRGVJKQB-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)