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Loperamide
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{{Short description|Medicine used to reduce diarrhea}} {{Use dmy dates|date=January 2024}} {{cs1 config |name-list-style=vanc |display-authors=6}} {{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 416898838 | image = Loperamide.svg | image_class = skin-invert-image | width = 250 | alt = | image2 = Loperamide ball-and-stick.png | image_class2 = bg-transparent | width2 = 235 | alt2 = | USAN = Loperamide hydrochloride <!-- Clinical data --> | pronounce = {{IPAc-en|l|oʊ|ˈ|p|ɛr|ə|m|aɪ|d}} | tradename = Imodium, others<ref name=Names/> | Drugs.com = {{drugs.com|monograph|loperamide-hydrochloride}} | MedlinePlus = a682280 | DailyMedID = Loperamide | pregnancy_AU = B3 | routes_of_administration = [[Oral administration|By mouth]] | ATC_prefix = A07 | ATC_suffix = DA03 | ATC_supplemental = <br />{{ATC|A07|DA05}} (oxide) | legal_AU = S2 | 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 = OTC | legal_UK = GSL | legal_US = OTC | legal_US_comment = / Rx-only<ref>{{cite web | title=Loperamide hydrochloride capsule | website=DailyMed | date=30 September 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=72a7ae47-cdf3-4949-b9f8-f29b153f787f | access-date=8 January 2024 | archive-date=14 September 2023 | archive-url=https://web.archive.org/web/20230914040736/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=72a7ae47-cdf3-4949-b9f8-f29b153f787f | url-status=live }}</ref> <!-- Pharmacokinetic data --> | bioavailability = 0.3% | protein_bound = 97% | metabolism = [[Liver]] (extensive) | elimination_half-life = 9–14 hours<ref name=AHFS2015/> | excretion = Feces (30–40%), urine (1%) <!-- Identifiers --> | IUPHAR_ligand = 7215 | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 53179-11-6 | PubChem = 3955 | DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank = DB00836 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 3818 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 6X9OC3H4II | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D08144 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 6532 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 841 | synonyms = R-18553 <!-- Chemical data --> | IUPAC_name = 4-[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]-''N,N''-dimethyl-2,2-diphenylbutanamide | C=29 | H=33 | Cl=1 | N=2 | O=2 | SMILES = ClC1=CC=C(C2(CCN(CC2)CCC(C3=CC=CC=C3)(C(N(C)C)=O)C4=CC=CC=C4)O)C=C1 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C29H33ClN2O2/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RDOIQAHITMMDAJ-UHFFFAOYSA-N }} <!-- Definition and medical uses --> '''Loperamide''', sold under the brand name '''Imodium''', among others,<ref name=Names>Drugs.com [https://www.drugs.com/international/loperamide.html International brands for loperamide] {{webarchive|url=https://web.archive.org/web/20150923230214/http://www.drugs.com/international/loperamide.html |date=23 September 2015 }} Page accessed 4 September 2015</ref> is a [[medication]] of the [[opioid receptor agonist]] class used to decrease the frequency of [[diarrhea]].<ref name="auto">{{Cite web|url=https://www.nhs.uk/medicines/loperamide/about-loperamide/|title=About loperamide|date=11 April 2024|website=nhs.uk}}</ref><ref name=AHFS2015>{{cite web|title=Loperamide Hydrochloride|url=https://www.drugs.com/monograph/loperamide-hydrochloride.html|publisher=The American Society of Health-System Pharmacists|access-date=25 August 2015|url-status=live|archive-url=https://web.archive.org/web/20150907231103/http://www.drugs.com/monograph/loperamide-hydrochloride.html|archive-date=7 September 2015}}</ref> It is often used for this purpose in [[irritable bowel syndrome]], [[inflammatory bowel disease]], [[short bowel syndrome]],<ref name=AHFS2015/> [[Crohn's disease]], and [[ulcerative colitis]].<ref name="auto"/> It is not recommended for those with [[dysentery|blood in the stool]], mucus in the stool, or [[Fever|fevers]].<ref name=AHFS2015/> The medication is [[Oral administration|taken by mouth]].<ref name=AHFS2015/> <!-- Side effects --> Common side effects include [[abdominal pain]], [[constipation]], [[sleepiness]], [[vomiting]], and [[dry mouth]].<ref name=AHFS2015/> It may increase the risk of [[toxic megacolon]].<ref name=AHFS2015/> Loperamide's safety in [[pregnancy]] is unclear, but no evidence of harm has been found.<ref name=AG2015>{{cite web|title=Prescribing medicines in pregnancy database|url=http://www.tga.gov.au/hp/medicines-pregnancy.htm|work=Australian Government|access-date=22 April 2014|date=3 March 2014|url-status=live|archive-url=https://web.archive.org/web/20140408040902/http://www.tga.gov.au/hp/medicines-pregnancy.htm |archive-date=8 April 2014}}</ref> It appears to be safe in [[breastfeeding]].<ref>{{cite web|title=Loperamide use while Breastfeeding|url=https://www.drugs.com/breastfeeding/loperamide.html|access-date=26 August 2015|url-status=live|archive-url=https://web.archive.org/web/20150908034709/http://www.drugs.com/breastfeeding/loperamide.html|archive-date=8 September 2015}}</ref> It is an [[opioid]] with no significant absorption from the gut and does not cross the [[blood–brain barrier]] when used at normal doses.<ref name=NCI2015Dic>{{cite web|title=loperamide hydrochloride|url=http://www.cancer.gov/publications/dictionaries/cancer-drug?CdrID=41911|website=NCI Drug Dictionary|access-date=26 August 2015|url-status=live|archive-url=https://web.archive.org/web/20150907211727/http://www.cancer.gov/publications/dictionaries/cancer-drug?CdrID=41911|archive-date=7 September 2015|date=2 February 2011}}</ref> It works by slowing the contractions of the [[intestines]].<ref name=AHFS2015/> <!-- History, society, and culture --> Loperamide was first made in 1969 and used medically in 1976.<ref name="Oxford University Press">{{cite book|vauthors=Patrick GL|title=An introduction to medicinal chemistry|date=2013|publisher=Oxford University Press|location=Oxford|isbn=9780199697397|pages=644|edition=Fifth|url=https://books.google.com/books?id=Pj7xJRuhZxUC&pg=PA644|access-date=17 December 2020|archive-date=14 January 2023|archive-url=https://web.archive.org/web/20230114195405/https://books.google.com/books?id=Pj7xJRuhZxUC&pg=PA644|url-status=live}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> Loperamide is available as a [[generic medication]].<ref name=AHFS2015/><ref name=Ric2013>{{cite book| vauthors = Hamilton RJ |title=Tarascon pocket pharmacopoeia|date=2013|publisher=Jones & Bartlett Learning|location=[Sudbury, Mass.]|isbn=9781449673611|pages = 217|edition=14|url=https://books.google.com/books?id=zJay-fZCFGgC&pg=PA217|url-status=live|archive-url=https://web.archive.org/web/20160305005322/https://books.google.com/books?id=zJay-fZCFGgC&pg=PA217|archive-date=5 March 2016}}</ref> In 2022, it was the 297th most commonly prescribed medication in the United States, with more than 400,000 prescriptions.<ref name="Top 300 of 2022">{{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 = Loperamide Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Loperamide | access-date = 30 August 2024 }}</ref>
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