Editing Amitriptyline (section)

{{Short description|Tricyclic antidepressant}}
{{Use American English|date=February 2024}}
{{Use dmy dates|date=September 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 477169407
| image = Amitriptyline2DACS.svg
| image_class = skin-invert-image
| width = 200
| alt =
| image2 = Amitriptyline-from-picrate-xtal-3D-balls.png
| width2 = 250
| alt2 =


| pronounce = {{IPAc-en|ˌ|æ|m|ᵻ|ˈ|t|ɹ|ɪ|p|t|ᵻ|l|iː|n}}<ref>{{cite web|url=https://www.lexico.com/en/definition/amitriptyline|archive-url=https://web.archive.org/web/20140714140116/http://www.oxforddictionaries.com/us/definition/english/amitriptyline?q=amitriptyline |url-status= dead |title=Amitriptyline |work= Oxford Dictionary |via= Lexico.com |archive-date=14 July 2014 | language= en |access-date=6 January 2021}}</ref>
| tradename = Elavil, others
| Drugs.com = {{drugs.com|monograph|amitriptyline-hydrochloride}}
| MedlinePlus = a682388
| DailyMedID = Amitriptyline
| pregnancy_AU = C
| pregnancy_AU_comment =<ref name="Drugs.com pregnancy">{{cite web | title=Amitriptyline Use During Pregnancy | website=Drugs.com | date=2 September 2020 | url=https://www.drugs.com/pregnancy/amitriptyline.html | access-date=13 September 2020 | archive-date=9 November 2020 | archive-url=https://web.archive.org/web/20201109214320/https://www.drugs.com/pregnancy/amitriptyline.html | url-status=live }}</ref>
| routes_of_administration = [[Oral administration|Oral]], [[intramuscular injection]]
| class = [[Tricyclic antidepressant]] (TCA)
| ATC_prefix = N06
| ATC_suffix = AA09
| legal_AU = S4
| legal_BR = C1
| legal_BR_comment = <ref>{{cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=31 March 2023 |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=3 August 2023 |access-date=16 August 2023 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=4 April 2023}}</ref>
| legal_CA = Rx-only
| legal_UK = POM
| legal_US = Rx-only
| bioavailability = 45%<ref name="pmid3893842"/>-53%<ref name = pmid33438398/>
| protein_bound = 96%<ref name = TGA/>
| metabolism = [[Liver]] (CYP2D6, CYP2C19, CYP3A4)<ref name="pmid15554244"/><ref name = pmid33438398/><ref name="pmid11583471"/>
| metabolites = nortriptyline, (''E'')-10-hydroxynortriptyline
| elimination_half-life = 21 hours<ref name="pmid3893842"/>
| excretion = [[Urine]]: 12–80% after 48 hours;<ref name="pmid6667101"/> feces: not studied
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 50-48-6
| CAS_supplemental = <br />549-18-8 ([[hydrochloride]])<br />17086-03-2 ([[embonate]])
| PubChem = 2160
| IUPHAR_ligand = 200
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00321
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2075
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1806D8D52K
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07448
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2666
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 629
| synonyms =
| IUPAC_name = 3-(10,11-dihydro-5''H''-dibenzo[''a'',''d'']cycloheptene-5-ylidene)-''N'',''N''-dimethylpropan-1-amine
| C=20 | H=23 | N=1
| SMILES = c3cc2c(/C(c1c(cccc1)CC2)=C\CCN(C)C)cc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KRMDCWKBEZIMAB-UHFFFAOYSA-N
| melting_point = 197.5
| melting_notes =<ref>{{cite journal |vauthors=Blessel KW, Rudy BC, Senkowski BZ |title=Amitriptyline Hydrochloride |journal=Analytical Profiles of Drug Substances |volume=3 |pages=127–148 |date=1974 |doi=10.1016/S0099-5428(08)60066-0|isbn=9780122608032 }}</ref><!-- all melting points for "amitriptyline" in the literature are for the hydrochloride salt -->
}}

'''Amitriptyline''', sold under the brand name '''Elavil''' among others, is a [[tricyclic antidepressant]] primarily used to treat [[major depressive disorder]], and a variety of pain syndromes such as [[neuropathic pain]], [[fibromyalgia]], [[migraine]] and [[tension headaches]].<ref name=EMC>{{cite web|title=Amitriptyline Tablets BP 50mg – Summary of Product Characteristics (SPC)|work=electronic Medicines Compendium|publisher=Actavis UK Ltd.|date=24 March 2013|access-date=1 December 2013|url=http://www.medicines.org.uk/emc/medicine/23738/SPC/Amitriptyline+Tablets+BP+50mg/|url-status=live|archive-url=https://web.archive.org/web/20131203015148/http://www.medicines.org.uk/emc/medicine/23738/SPC/Amitriptyline+Tablets+BP+50mg/|archive-date=3 December 2013}}</ref> Due to the frequency and prominence of side effects, amitriptyline is generally considered a [[Therapy#Lines of therapy|second-line therapy]] for these indications.<ref name=top100drugs/><ref name="pmid32040849"/><ref name="pmid27377815"/><ref name="pmid22529202"/>

The most common side effects are dry mouth, drowsiness, dizziness, constipation, and weight gain. [[Glaucoma]], liver toxicity and [[arrhythmia|abnormal heart rhythms]] are rare but serious side effects. Blood levels of amitriptyline vary significantly from one person to another,<ref name="pmid28405886">{{cite journal | vauthors = Tfelt-Hansen P, Ågesen FN, Pavbro A, Tfelt-Hansen J | title = Pharmacokinetic Variability of Drugs Used for Prophylactic Treatment of Migraine | journal = CNS Drugs | volume = 31 | issue = 5 | pages = 389–403 | date = May 2017 | pmid = 28405886 | doi = 10.1007/s40263-017-0430-3 | s2cid = 23560743 }}</ref> and amitriptyline interacts with many other medications potentially aggravating its side effects.

Amitriptyline was discovered in the late 1950s by scientists at [[Merck & Co.|Merck]] and approved by the US [[Food and Drug Administration]] (FDA) in 1961.<ref name="Half a century of antidepressant dr">{{cite journal | vauthors = Fangmann P, Assion HJ, Juckel G, González CA, López-Muñoz F | title = Half a century of antidepressant drugs: on the clinical introduction of monoamine oxidase inhibitors, tricyclics, and tetracyclics. Part II: tricyclics and tetracyclics | journal = Journal of Clinical Psychopharmacology | volume = 28 | issue = 1 | pages = 1–4 | date = February 2008 | pmid = 18204333 | doi = 10.1097/jcp.0b013e3181627b60 | s2cid = 31018835 }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> It is available as a [[generic medication]].<ref name=AHFS2014>{{cite web| title= Amitriptyline Hydrochloride| url= https://www.drugs.com/monograph/amitriptyline-hydrochloride.html |publisher= The American Society of Health-System Pharmacists| website= Drugs.com| access-date=25 September 2014|url-status=live| archive-url= https://web.archive.org/web/20140924185142/http://www.drugs.com/monograph/amitriptyline-hydrochloride.html|archive-date=24 September 2014}}</ref> In 2022, it was the 87th most commonly prescribed medication in the United States, with more than 7{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Amitriptyline Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Amitriptyline | access-date = 30 August 2024 | archive-date = 30 April 2017 | archive-url = https://web.archive.org/web/20170430155658/https://clincalc.com/DrugStats/Drugs/Amitriptyline | url-status = live }}</ref>
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