| Revision as of 11:21, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 477105717 of page Desipramine for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 19:50, 22 December 2024 edit Citation bot (talk | contribs)Bots5,424,128 edits Altered volume. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Sodium channel blockers | #UCB_Category 3/77 |
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{{Short description|Antidepressant}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Distinguish|depramine}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 477166380 |
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| Verifiedfields = changed |
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| verifiedrevid = 460777705 |
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| IUPAC_name = 3-(10,11-dihydro-5''H''-dibenzoazepin-5-yl)-''N''-methylpropan-1-amine |
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| IUPAC_name = 3-(10,11-dihydro-5''H''-dibenzoazepin-5-yl)-''N''-methylpropan-1-amine |
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| image = Desipramine.svg |
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| image = Desipramine.svg |
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| alt = Skeletal formula of desipramine |
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| width = 200px |
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| image2 = Desipramine-3D-balls.png |
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| alt2 = Ball-and-stick model of the desipramine molecule |
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| width2 = 225px |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = Norpramin |
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| tradename = Norpramin, Pertofrane, others |
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| Drugs.com = {{drugs.com|monograph|desipramine-hydrochloride}} |
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| Drugs.com = {{drugs.com|monograph|desipramine-hydrochloride}} |
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| MedlinePlus = a682387 |
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| MedlinePlus = a682387 |
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| pregnancy_US = N |
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| pregnancy_category = X (US) |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_status = Rx-only |
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| legal_BR = C1 |
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| routes_of_administration = Oral |
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| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_DE = <!-- Anlage I, II, III or Unscheduled --> |
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| legal_NZ = <!-- Class A, B, C --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = Rx-only |
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| legal_EU = |
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| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> |
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| routes_of_administration = ], ] |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = 60–70%<ref name="LemkeWilliams2012">{{cite book| vauthors = Lemke TL, Williams DA |title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA588|date=24 January 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-60913-345-0|pages=588–}}</ref> |
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| bioavailability = 73-92% |
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| protein_bound = 91%<ref name="LemkeWilliams2012" /> |
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| metabolism = ] |
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| metabolism = ] (])<ref name=clinp>{{cite journal | vauthors = Sallee FR, Pollock BG | title = Clinical pharmacokinetics of imipramine and desipramine | journal = Clinical Pharmacokinetics | volume = 18 | issue = 5 | pages = 346–364 | date = May 1990 | pmid = 2185906 | doi = 10.2165/00003088-199018050-00002 | s2cid = 37529573 }}</ref> |
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| elimination_half-life = 21-23 hours |
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| elimination_half-life = 12–30 hours<ref name="LemkeWilliams2012" /> |
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| excretion = ] |
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| excretion = ] (70%), ]<ref name="LemkeWilliams2012" /> |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 50-47-5 |
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| CAS_number = 50-47-5 |
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| CAS_supplemental = <br />58-28-6 (])<br />62265-06-9 (]) |
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| ATC_prefix = N06 |
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| ATC_prefix = N06 |
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| ATC_suffix = AA01 |
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| ATC_suffix = AA01 |
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| PubChem = 2995 |
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| PubChem = 2995 |
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| IUPHAR_ligand = 2399 |
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| IUPHAR_ligand = 2399 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB01151 |
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| DrugBank = DB01151 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 72 |
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| ChEMBL = 72 |
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| synonyms = Desmethylimipramine; Norimipramine; EX-4355; G-35020; JB-8181; NSC-114901<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Drugs.com" /> |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=18 | H=22 | N=2 |
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| C=18 | H=22 | N=2 |
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| SMILES = c1cc3c(cc1)CCc2c(cccc2)N3CCCNC |
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| molecular_weight = 266.381 g/mol |
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| smiles = c1cc3c(cc1)CCc2c(cccc2)N3CCCNC |
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| InChI = 1/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3 |
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| InChIKey = HCYAFALTSJYZDH-UHFFFAOYAV |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3 |
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| StdInChI = 1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3 |
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| StdInChIKey = HCYAFALTSJYZDH-UHFFFAOYSA-N |
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| StdInChIKey = HCYAFALTSJYZDH-UHFFFAOYSA-N |
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}} |
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}} |
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'''Desipramine''', sold under the brand name '''Norpramin''' among others, is a ] (TCA) used in the treatment of ].<ref name="GG">{{cite book | isbn = 978-0-07-162442-8 | title = Goodman and Gilman's The Pharmacological Basis of Therapeutics | edition = 12th | vauthors = Brunton L, Chabner B, Knollman B | year = 2010 | publisher = McGraw-Hill Professional | location = New York | title-link = Goodman and Gilman's The Pharmacological Basis of Therapeutics }}</ref> It acts as a relatively selective ], though it does also have other activities such as weak ]y, ], ], and ] effects. The drug is not considered a first-line treatment for depression since the introduction of ] (SSRI) ]s, which have fewer ]s and are safer in ]. |
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==Medical uses== |
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Desipramine is primarily used for the treatment of depression.<ref name = GG/> It may also be useful to treat symptoms of ] (ADHD).<ref>{{cite journal | vauthors = Ghanizadeh A | title = A systematic review of the efficacy and safety of desipramine for treating ADHD | journal = Current Drug Safety | volume = 8 | issue = 3 | pages = 169–174 | date = July 2013 | pmid = 23914752 | doi = 10.2174/15748863113089990029 }}</ref> Evidence of benefit is only in the short term, and with concerns of side effects its overall usefulness is not clear.<ref>{{cite journal | vauthors = Otasowie J, Castells X, Ehimare UP, Smith CH | title = Tricyclic antidepressants for attention deficit hyperactivity disorder (ADHD) in children and adolescents | journal = The Cochrane Database of Systematic Reviews | volume = 2014 | issue = 9 | pages = CD006997 | date = September 2014 | pmid = 25238582 | doi = 10.1002/14651858.CD006997.pub2 | pmc = 11236426 }}</ref> Desipramine at very low doses is also used to help reduce the pain associated with ].<ref>{{cite web|url=http://www.uptodate.com/contents/upset-stomach-functional-dyspepsia-in-adults-beyond-the-basics|title=UpToDate|website=www.uptodate.com}}</ref> It has also been tried, albeit with little evidence of effectiveness, in the treatment of ].<ref>{{cite journal | vauthors = Pani PP, Trogu E, Vecchi S, Amato L | title = Antidepressants for cocaine dependence and problematic cocaine use | journal = The Cochrane Database of Systematic Reviews | issue = 12 | pages = CD002950 | date = December 2011 | pmid = 22161371 | doi = 10.1002/14651858.CD002950.pub3 }}</ref> Evidence for usefulness in ] is also poor.<ref name="pmid25246131">{{cite journal | vauthors = Hearn L, Moore RA, Derry S, Wiffen PJ, Phillips T | title = Desipramine for neuropathic pain in adults | journal = The Cochrane Database of Systematic Reviews | volume = 2014 | issue = 9 | pages = CD011003 | date = September 2014 | pmid = 25246131 | pmc = 6804291 | doi = 10.1002/14651858.CD011003.pub2 | veditors = Hearn L }}</ref> |
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==Side effects== |
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Desipramine tends to be less ] than other TCAs and tends to produce fewer ] effects such as ], ], ], ], and ] or ]s.<ref name = MD>{{cite web|title=Desipramine Hydrochloride|work=Martindale: The Complete Drug Reference|publisher=Pharmaceutical Press|location=London, UK|date=13 December 2013|access-date=17 July 2014|url=https://www.medicinescomplete.com/mc/martindale/current/2509-y.htm}}</ref> |
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==Overdose== |
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{{Main|Tricyclic antidepressant overdose}} |
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Desipramine is particularly toxic in cases of overdose, compared to other antidepressants.<ref>{{cite journal | vauthors = White N, Litovitz T, Clancy C | title = Suicidal antidepressant overdoses: a comparative analysis by antidepressant type | journal = Journal of Medical Toxicology | volume = 4 | issue = 4 | pages = 238–250 | date = December 2008 | pmid = 19031375 | pmc = 3550116 | doi = 10.1007/BF03161207 }}</ref> Any overdose or suspected overdose of desipramine is considered to be a medical emergency and can result in death without prompt medical intervention. |
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==Pharmacology== |
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===Pharmacodynamics=== |
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{{See also|Pharmacology of antidepressants|Tricyclic antidepressant#Binding profiles}} |
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{| class="wikitable floatleft" style="font-size:small;" |
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|+ Desipramine<ref name="PDSP">{{cite web | title = PDSP K<sub>i</sub> Database | work = Psychoactive Drug Screening Program (PDSP)|author1-link=Bryan Roth | vauthors = Roth BL, Driscol J | publisher = University of North Carolina at Chapel Hill and the United States National Institute of Mental Health | access-date = 7 May 2022 | url = https://pdsp.unc.edu/databases/pdsp.php?receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=Desipramine&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query}}</ref> |
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! Site !! K<sub>i</sub> (nM) !! Species !! Ref |
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|{{abbrlink|SERT|Serotonin transporter}}|| 17.6–163 || Human ||<ref name="pmid9537821">{{cite journal | vauthors = Tatsumi M, Groshan K, Blakely RD, Richelson E | title = Pharmacological profile of antidepressants and related compounds at human monoamine transporters | journal = European Journal of Pharmacology | volume = 340 | issue = 2–3 | pages = 249–258 | date = December 1997 | pmid = 9537821 | doi = 10.1016/s0014-2999(97)01393-9 }}</ref><ref name="pmid9400006">{{cite journal | vauthors = Owens MJ, Morgan WN, Plott SJ, Nemeroff CB | title = Neurotransmitter receptor and transporter binding profile of antidepressants and their metabolites | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 283 | issue = 3 | pages = 1305–1322 | date = December 1997 | pmid = 9400006 }}</ref> |
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|{{abbrlink|NET|Norepinephrine transporter}}|| 0.63–3.5 || Human ||<ref name="pmid9537821" /><ref name="pmid9400006" /> |
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| {{abbrlink|DAT|Dopamine transporter}} || 3,190 || Human || <ref name="pmid9537821" /> |
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| ] || ≥6,400 || Human || <ref name="pmid7855217" /><ref name="pmid3816971">{{cite journal | vauthors = Wander TJ, Nelson A, Okazaki H, Richelson E | title = Antagonism by antidepressants of serotonin S1 and S2 receptors of normal human brain in vitro | journal = European Journal of Pharmacology | volume = 132 | issue = 2–3 | pages = 115–121 | date = December 1986 | pmid = 3816971 | doi = 10.1016/0014-2999(86)90596-0 }}</ref> |
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|]|| 115–350 || Human ||<ref name="pmid7855217" /><ref name="pmid3816971" /> |
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| ] || 244–748 || Rat || <ref name="pmid8876023">{{cite journal | vauthors = Pälvimäki EP, Roth BL, Majasuo H, Laakso A, Kuoppamäki M, Syvälahti E, Hietala J | title = Interactions of selective serotonin reuptake inhibitors with the serotonin 5-HT2c receptor | journal = Psychopharmacology | volume = 126 | issue = 3 | pages = 234–240 | date = August 1996 | pmid = 8876023 | doi = 10.1007/bf02246453 | s2cid = 24889381 }}</ref><ref name="pmid9686407">{{cite journal | vauthors = Toll L, Berzetei-Gurske IP, Polgar WE, Brandt SR, Adapa ID, Rodriguez L, Schwartz RW, Haggart D, O'Brien A, White A, Kennedy JM, Craymer K, Farrington L, Auh JS | display-authors = 6 | title = Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications | journal = NIDA Research Monograph | volume = 178 | pages = 440–466 | date = March 1998 | pmid = 9686407 }}</ref> |
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| ] || ≥2,500 || Rodent || <ref name="pmid9686407" /><ref name="pmid2533080">{{cite journal | vauthors = Schmidt AW, Hurt SD, Peroutka SJ | title = 'quipazine' degradation products label 5-HT uptake sites | journal = European Journal of Pharmacology | volume = 171 | issue = 1 | pages = 141–143 | date = November 1989 | pmid = 2533080 | doi = 10.1016/0014-2999(89)90439-1 | doi-access = free }}</ref> |
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| ] || >1,000 || Rat || <ref name="pmid8394362">{{cite journal | vauthors = Shen Y, Monsma FJ, Metcalf MA, Jose PA, Hamblin MW, Sibley DR | title = Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype | journal = The Journal of Biological Chemistry | volume = 268 | issue = 24 | pages = 18200–18204 | date = August 1993 | pmid = 8394362 | doi = 10.1016/S0021-9258(17)46830-X | doi-access = free }}</ref> |
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|]|| 23–130 || Human ||<ref name="pmid7855217" /><ref name="pmid6086881" /><ref name="pmid9400006" /> |
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| ] || ≥1,379 || Human || <ref name="pmid7855217" /><ref name="pmid6086881" /><ref name="pmid9400006" /> |
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| ] || ≥1,700 || Rat || <ref name="pmid3790168">{{cite journal | vauthors = Muth EA, Haskins JT, Moyer JA, Husbands GE, Nielsen ST, Sigg EB | title = Antidepressant biochemical profile of the novel bicyclic compound Wy-45,030, an ethyl cyclohexanol derivative | journal = Biochemical Pharmacology | volume = 35 | issue = 24 | pages = 4493–4497 | date = December 1986 | pmid = 3790168 | doi = 10.1016/0006-2952(86)90769-0 }}</ref><ref name="pmid10379421">{{cite journal | vauthors = Sánchez C, Hyttel J | title = Comparison of the effects of antidepressants and their metabolites on reuptake of biogenic amines and on receptor binding | journal = Cellular and Molecular Neurobiology | volume = 19 | issue = 4 | pages = 467–489 | date = August 1999 | pmid = 10379421 | doi = 10.1023/A:1006986824213 | s2cid = 19490821 }}</ref> |
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| ] || 410 || Human || <ref name="pmid16844100">{{cite journal | vauthors = Benjamin ER, Pruthi F, Olanrewaju S, Shan S, Hanway D, Liu X, Cerne R, Lavery D, Valenzano KJ, Woodward RM, Ilyin VI | display-authors = 6 | title = Pharmacological characterization of recombinant N-type calcium channel (Cav2.2) mediated calcium mobilization using FLIPR | journal = Biochemical Pharmacology | volume = 72 | issue = 6 | pages = 770–782 | date = September 2006 | pmid = 16844100 | doi = 10.1016/j.bcp.2006.06.003 }}</ref> |
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| ] || 5,460 || Human || <ref name="pmid17850785">{{cite journal | vauthors = Deupree JD, Montgomery MD, Bylund DB | title = Pharmacological properties of the active metabolites of the antidepressants desipramine and citalopram | journal = European Journal of Pharmacology | volume = 576 | issue = 1–3 | pages = 55–60 | date = December 2007 | pmid = 17850785 | pmc = 2231336 | doi = 10.1016/j.ejphar.2007.08.017 }}</ref> |
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| ] || 3,400 || Human || <ref name="pmid7855217" /><ref name="pmid6086881" /> |
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|]|| 60–110 || Human ||<ref name="pmid7855217">{{cite journal | vauthors = Cusack B, Nelson A, Richelson E | title = Binding of antidepressants to human brain receptors: focus on newer generation compounds | journal = Psychopharmacology | volume = 114 | issue = 4 | pages = 559–565 | date = May 1994 | pmid = 7855217 | doi = 10.1007/bf02244985 | s2cid = 21236268 }}</ref><ref name="pmid6086881">{{cite journal | vauthors = Richelson E, Nelson A | title = Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 230 | issue = 1 | pages = 94–102 | date = July 1984 | pmid = 6086881 }}</ref><ref name="pmid22033803">{{cite journal | vauthors = Appl H, Holzammer T, Dove S, Haen E, Strasser A, Seifert R | title = Interactions of recombinant human histamine H₁R, H₂R, H₃R, and H₄R receptors with 34 antidepressants and antipsychotics | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 385 | issue = 2 | pages = 145–170 | date = February 2012 | pmid = 22033803 | doi = 10.1007/s00210-011-0704-0 | s2cid = 14274150 }}</ref> |
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| ] || 1,550 || Human || <ref name="pmid22033803" /> |
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| ] || >100,000 || Human || <ref name="pmid22033803" /> |
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| ] || 9,550 || Human || <ref name="pmid22033803" /> |
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|{{abbrlink|mACh|Muscarinic acetylcholine receptor}}|| 66–198 || Human ||<ref name="pmid7855217" /><ref name="pmid6086881" /> |
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| ''' ''']|| 110 || Human ||<ref name="pmid8100134">{{cite journal | vauthors = Stanton T, Bolden-Watson C, Cusack B, Richelson E | title = Antagonism of the five cloned human muscarinic cholinergic receptors expressed in CHO-K1 cells by antidepressants and antihistaminics | journal = Biochemical Pharmacology | volume = 45 | issue = 11 | pages = 2352–2354 | date = June 1993 | pmid = 8100134 | doi = 10.1016/0006-2952(93)90211-e }}</ref> |
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| ] || 540 || Human || <ref name="pmid8100134" /> |
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| ] || 210 || Human || <ref name="pmid8100134" /> |
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| ''' ''']|| 160 || Human ||<ref name="pmid8100134" /> |
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| ''' ''']|| 143 || Human ||<ref name="pmid8100134" /> |
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| ] || 1,990–4,000 || Rodent || <ref name="pmid2877462">{{cite journal | vauthors = Weber E, Sonders M, Quarum M, McLean S, Pou S, Keana JF | title = 1,3-Di(2-tolyl)guanidine: a selective ligand that labels sigma-type receptors for psychotomimetic opiates and antipsychotic drugs | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 83 | issue = 22 | pages = 8784–8788 | date = November 1986 | pmid = 2877462 | pmc = 387016 | doi = 10.1073/pnas.83.22.8784 | doi-access = free | bibcode = 1986PNAS...83.8784W }}</ref><ref name="pmid20373470">{{cite journal | vauthors = Hindmarch I, Hashimoto K | title = Cognition and depression: the effects of fluvoxamine, a sigma-1 receptor agonist, reconsidered | journal = Human Psychopharmacology | volume = 25 | issue = 3 | pages = 193–200 | date = April 2010 | pmid = 20373470 | doi = 10.1002/hup.1106 | s2cid = 26491662 }}</ref> |
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| ] || ≥1,611 || Rat || <ref name="PDSP" /><ref name="pmid20373470" /> |
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| colspan="4" style="width: 1px;" | Values are K<sub>i</sub> (nM). The smaller the value, the more strongly the drug binds to the site. |
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Desipramine is a very potent and relatively selective ] (NRI), which is thought to enhance ] ].<ref name="MartinVolkmar2007" /><ref name="pmid6384207">{{cite journal | vauthors = Janowsky DS, Byerley B | title = Desipramine: an overview | journal = The Journal of Clinical Psychiatry | volume = 45 | issue = 10 Pt 2 | pages = 3–9 | date = October 1984 | pmid = 6384207 }}</ref> Based on one study, it has the highest affinity for the ] (NET) of any other TCA,<ref name="pmid9537821" /> and is said to be the most noradrenergic<ref name="Curtin2016" /> and the most selective for the NET of the TCAs.<ref name="MartinVolkmar2007">{{cite book| vauthors = Martin A, Volkmar FR, Lewis M |title=Lewis's Child and Adolescent Psychiatry: A Comprehensive Textbook|url=https://books.google.com/books?id=s9Jdn43iac8C&pg=PA764|year=2007|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-6214-4|pages=764–}}</ref> The observed effectiveness of desipramine in the treatment of ADHD was the basis for the development of the selective NRI ] and its use in ADHD.<ref name="MartinVolkmar2007" /> |
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Desipramine has the weakest ] and ] effects of the TCAs.<ref name="GoldCarman1984">{{cite book| vauthors = Gold MS, Carman JS, Lydiard RB |title=Advances in Psychopharmacology|url=https://books.google.com/books?id=wwP1iOanWAAC&pg=PA98|date=2 July 1984|publisher=CRC Press|isbn=978-0-8493-5680-3|pages=98–}}</ref><ref name="Curtin2016">{{cite book| vauthors = Curtin C |title=Pain Management, An Issue of Hand Clinics, E-Book|url=https://books.google.com/books?id=TeGZCwAAQBAJ&pg=PA55|date=19 January 2016|publisher=Elsevier Health Sciences|isbn=978-0-323-41691-7|pages=55–}}</ref><ref name="BaylessDiehl2005">{{cite book| vauthors = Bayless TM, Diehl A |title=Advanced Therapy in Gastroenterology and Liver Disease|url=https://books.google.com/books?id=XR-Jsxz0qRwC&pg=PA263|year=2005|publisher=PMPH-USA|isbn=978-1-55009-248-6|pages=263–}}</ref> It tends to be slightly ] rather than ], unlike most others TCAs.<ref name="Curtin2016" /> Whereas other TCAs are useful for treating ], desipramine can cause insomnia as a side effect due to its activating properties.<ref name="Curtin2016" /> The drug is also not associated with ], in contrast to many other TCAs.<ref name="Curtin2016" /> Secondary amine TCAs like desipramine and ] have a lower risk of ] than other TCAs,<ref name="Leigh2012">{{cite book| vauthors = Leigh H |title=Biopsychosocial Approaches in Primary Care: State of the Art and Challenges for the 21st Century|url=https://books.google.com/books?id=5kcIBgAAQBAJ&pg=PA108|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4615-5957-3|pages=108–}}</ref><ref name="HalesYudofsky2011">{{cite book| vauthors = Hales RE, Yudofsky SC, Gabbard GO |title=Essentials of Psychiatry|url=https://books.google.com/books?id=Hf50vMMMv_wC&pg=PA468|year=2011|publisher=American Psychiatric Pub|isbn=978-1-58562-933-6|pages=468–}}</ref> although desipramine can still cause moderate orthostatic hypotension.<ref name="Rakel2007">{{cite book| vauthors = Rakel RE |title=Textbook of Family Medicine E-Book|url=https://books.google.com/books?id=ntcoDwAAQBAJ&pg=PA313|date=May 2007|publisher=Elsevier Health Sciences|isbn=978-1-4377-2190-4|pages=313–}}</ref> |
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===Pharmacokinetics=== |
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Desipramine is the major ] of ] and ].<ref name="pmid2891742">{{cite journal | vauthors = Leonard BE | title = A comparison of the pharmacological properties of the novel tricyclic antidepressant lofepramine with its major metabolite, desipramine: a review | journal = International Clinical Psychopharmacology | volume = 2 | issue = 4 | pages = 281–297 | date = October 1987 | pmid = 2891742 | doi = 10.1097/00004850-198710000-00001 }}</ref> |
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==Chemistry== |
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Desipramine is a ], specifically a ], and possesses three ]s fused together with a ] attached in its ].<ref name="Ritsner2013">{{cite book | vauthors= Ritsner MS |title=Polypharmacy in Psychiatry Practice, Volume I: Multiple Medication Use Strategies|url=https://books.google.com/books?id=jy-LMZU7338C&pg=PA270|date=15 February 2013|publisher=Springer Science & Business Media|isbn=978-94-007-5805-6|pages=270–271}}</ref> Other dibenzazepine TCAs include ] (''N''-methyldesipramine), ], ], and ] (''N''-(4-chlorobenzoylmethyl)desipramine).<ref name="Ritsner2013" /><ref name="LemkeWilliams2008">{{cite book| vauthors = Lemke TL, Williams DA |title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=R0W1ErpsQpkC&pg=PA580|year=2008|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-6879-5|pages=580–}}</ref> Desipramine is a ] TCA, with its ''N''-] ] imipramine being a ].<ref name="CutlerSramek1994">{{cite book| vauthors = Cutler NR, Sramek JJ, Narang PK |title=Pharmacodynamics and Drug Development: Perspectives in Clinical Pharmacology|url=https://books.google.com/books?id=ncRXa8Dq88QC&pg=PA160|date=20 September 1994|publisher=John Wiley & Sons|isbn=978-0-471-95052-3|pages=160–}}</ref><ref name="AnzenbacherZanger2012">{{cite book| vauthors = Anzenbacher P, Zanger UM |title=Metabolism of Drugs and Other Xenobiotics|url=https://books.google.com/books?id=f-XHh17NfwgC&pg=PA302|date=23 February 2012|publisher=John Wiley & Sons|isbn=978-3-527-64632-6|pages=302–}}</ref> Other secondary amine TCAs include ] and ].<ref name="Anthony2002">{{cite book| vauthors = Anthony PK |title=Pharmacology Secrets|url=https://books.google.com/books?id=_QQsj3PAUrEC&pg=PA39|year=2002|publisher=Elsevier Health Sciences|isbn=978-1-56053-470-9|pages=39–}}</ref><ref name="CowenHarrison2012">{{cite book| vauthors = Cowen P, Harrison P, Burns T |title= Shorter Oxford Textbook of Psychiatry|url=https://books.google.com/books?id=Y1DtSGq-LnoC&pg=PA532|date=9 August 2012|publisher=OUP Oxford|isbn=978-0-19-162675-3|pages=532–}}</ref> The ] of desipramine is 3-(10,11-dihydro-5''H''-dibenzoazepin-5-yl)-''N''-methylpropan-1-amine and its ] form has a ] of C<sub>18</sub>H<sub>22</sub>N<sub>2</sub> with a ] of 266.381 g/mol.<ref name="Elks2014" /> The drug is used commercially mostly as the ] ]; the ] salt is or has been used for ] in ] (brand name Nebril) and the free base form is not used.<ref name="Elks2014" /><ref name="IndexNominum2000" /> The ] of the free base is 50-47-5, of the hydrochloride is 58-28-6, and of the dibudinate is 62265-06-9.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="ChemIDplus">{{cite web|url=https://chem.nlm.nih.gov/chemidplus/rn/62265-06-9| work = ChemIDplus | title = Desipramine dibudinate | publisher = U.S. National Library of Medicine | vauthors = Chambers M }}</ref> |
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==History== |
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Desipramine was developed by ].<ref name="pmid19557250">{{cite journal | vauthors = Andersen J, Kristensen AS, Bang-Andersen B, Strømgaard K | title = Recent advances in the understanding of the interaction of antidepressant drugs with serotonin and norepinephrine transporters | journal = Chemical Communications | issue = 25 | pages = 3677–3692 | date = July 2009 | pmid = 19557250 | doi = 10.1039/b903035m }}</ref> It first appeared in the literature in 1959 and was patented in 1962.<ref name="pmid19557250" /> The drug was first introduced for the treatment of depression in 1963 or 1964.<ref name="pmid19557250" /><ref name="Dart2004">{{cite book| vauthors = Dart RC |title=Medical Toxicology|url=https://books.google.com/books?id=BfdighlyGiwC&pg=PA836|year=2004|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-2845-4|pages=836–}}</ref> |
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==Society and culture== |
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===Generic names=== |
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''Desipramine'' is the ] of the drug and its {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|BAN|British Approved Name}}, while ''desipramine hydrochloride'' is its {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|USP|United States Pharmacopeia}}, {{abbrlink|BAN|British Approved Name}}, and {{abbrlink|JAN|Japanese Accepted Name}}.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA363|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=363–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA304|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=304–}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA94|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=94–}}</ref><ref name="Drugs.com">{{cite web|url=https://www.drugs.com/international/desipramine.html|title=Desipramine - Drugs.com|website=drugs.com}}</ref> Its generic name in ] and its {{abbrlink|DCF|Dénomination Commune Française}} are ''désipramine'', in ] and ] and its {{abbrlink|DCIT|Denominazione Comune Italiana}} are ''desipramina'', in ] is ''desipramin'', and in ] is ''desipraminum''.<ref name="IndexNominum2000" /><ref name="Drugs.com" /> |
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===Brand names=== |
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Desipramine is or has been marketed throughout the world under a variety of brand names, including Irene, Nebril, Norpramin, Pertofran, Pertofrane, Pertrofran, and Petylyl among others.<ref name="IndexNominum2000" /><ref name="Drugs.com" /> |
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== References == |
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