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Revision as of 11:42, 23 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 461287243 of page Levamisole for the Chem/Drugbox validation project (updated: 'DrugBank').  Latest revision as of 18:58, 3 August 2024 edit GreenC bot (talk | contribs)Bots2,547,789 edits Move 1 url. Wayback Medic 2.5 per WP:URLREQ#nbcnews.com 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=March 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 420063529 | verifiedrevid = 462090529
| image = Levamisole.svg
| IUPAC_name = (''S'')-6-Phenyl-2,3,5,6-tetrahydroimidazothiazole
| width = 180
| image = Levamisole2.svg
| alt = Skeletal formula of levamisole
| width = 200
| image2 = Levamisole molecule ball.png
| alt2 = Ball-and-stick model of the levamisole molecule


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Decaris, Ergamisol
| Drugs.com = {{drugs.com|CONS|levamisole}} | Drugs.com = {{drugs.com|CONS|levamisole}}
| MedlinePlus = a697011 | MedlinePlus = a697011
| DailyMedID = Levamisole
| pregnancy_AU =
| pregnancy_US = | pregnancy_AU =
| routes_of_administration = ]
| legal_status =
| ATC_prefix = P02
| routes_of_administration = Oral
| ATC_suffix = CE01
| ATC_supplemental = {{ATCvet|P52|AE01}}

| legal_CA =
| legal_CA_comment = Withdrawn{{cn|date=March 2024}}
| legal_US =
| legal_US_comment = Withdrawn{{cn|date=March 2024}}
| legal_status = Rx-only (])


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| metabolism = ] | metabolism = ]
| elimination_half-life = 4.4-5.6 hours (biphasic) | elimination_half-life = 3–4 hours
| excretion = | excretion = ] (70%)


<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 7210
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 14769-73-4 | CAS_number = 14769-73-4
| ATC_prefix = P02
| ATC_suffix = CE01
| ATC_supplemental = {{ATCvet|P52|AE01}}
| PubChem = 26879 | PubChem = 26879
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08114 | KEGG = D08114
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 6432
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1454 | ChEMBL = 1454


<!--Chemical data--> <!--Chemical data-->
| IUPAC_name = (''S'')-6-Phenyl-2,3,5,6-tetrahydroimidazo thiazole
| C=11 | H=12 | N=2 | S=1
| C=11 | H=12 | N=2 | S=1
| molecular_weight = 204.292 g/mol
| smiles = N\2=C1/SCCN1C/2c3ccccc3 | smiles = N\2=C1/SCCN1C/2c3ccccc3
| InChI = 1/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1
| InChIKey = HLFSDGLLUJUHTE-SNVBAGLBBU
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1 | StdInChI = 1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1
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| StdInChIKey = HLFSDGLLUJUHTE-SNVBAGLBSA-N | StdInChIKey = HLFSDGLLUJUHTE-SNVBAGLBSA-N
| density = 1.31 | density = 1.31
| melting_point = 230 | melting_point = 60
| solubility = hydrochloride: 210
}} }}

<!-- Definition and medical uses -->
'''Levamisole''', sold under the brand name '''Ergamisol''' among others, is a medication used to treat ] infections, specifically ] and ]s.<ref>{{cite journal | vauthors = Keiser J, Utzinger J | title = Efficacy of current drugs against soil-transmitted helminth infections: systematic review and meta-analysis | journal = JAMA | volume = 299 | issue = 16 | pages = 1937–48 | date = April 2008 | pmid = 18430913 | doi = 10.1001/jama.299.16.1937 }}</ref> It is taken by mouth.<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | hdl-access=free | pages=86, 590}}</ref>

<!-- Side effects and mechanism -->
Side effects may include abdominal pain, vomiting, headache, and dizziness.<ref name=WHO2008/> Use is not recommended during ] or the ] of ].<ref name=WHO2008/> Serious side effects may include an increased risk of infection.<ref name=Cons2016>{{cite web|title=Levamisole Advanced Patient Information - Drugs.com|url=https://www.drugs.com/cons/levamisole.html|website=www.drugs.com|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220222556/https://www.drugs.com/cons/levamisole.html|archive-date=20 December 2016}}</ref> It belongs to the ] class of medications.<ref name=Cons2016/>

<!-- History -->
Levamisole was invented in 1966 in ] by ].<ref>{{cite book| vauthors = Prevenier W, Howelland M |title=From reliable sources : an introduction to historical methods|date=2001|publisher=Cornell university press|location=Ithaca|isbn=9780801485602|page=77|edition=1st |url=https://books.google.com/books?id=wSqgwOZPjJ4C&pg=PA77|url-status=live|archive-url=https://web.archive.org/web/20170910151722/https://books.google.com/books?id=wSqgwOZPjJ4C&pg=PA77|archive-date=10 September 2017}}</ref> It is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> Levamisole is also used as a ] for cattle.<ref name="Valcor FDA label" /><ref>{{cite book| vauthors = Taylor MA, Coop RL, Wall RL |title=Veterinary Parasitology|date=2015|publisher=John Wiley & Sons|isbn=9781119073673|page=329|url=https://books.google.com/books?id=ta7YCgAAQBAJ&pg=PA329|language=en|url-status=live|archive-url=https://web.archive.org/web/20170910151722/https://books.google.com/books?id=ta7YCgAAQBAJ&pg=PA329|archive-date=10 September 2017}}</ref>

==Medical uses==

===Worms===
Levamisole was originally used as an ] to treat worm infestations in both humans and animals. Levamisole works as a ] ] that causes continued stimulation of the parasitic worm muscles, leading to paralysis.<ref>{{cite web|title=Levamisole | work = Martindale: The Complete Drug Reference |url=http://online.lexi.com/lco/action/doc/retrieve/docid/martindale_f/1351191| publisher =Lexicomp|access-date=21 April 2014|url-status=live|archive-url= https://web.archive.org/web/20161221163156/http://online.lexi.com/lco/action/doc/retrieve/docid/martindale_f/1351191|archive-date=21 December 2016}}</ref> Levamisole has gained prominence among ] as an effective treatment for '']'' ] infestations in ] ].<ref>{{cite web | vauthors = Sanford S |title = Levamisole Hydrochloride: Its application and usage in freshwater aquariums |publisher = Loaches Online |year = 2007 |url = http://www.loaches.com/disease-treatment/levamisole-hydrochloride-1 |access-date = 27 February 2009 |url-status = live |archive-url = https://web.archive.org/web/20090301001606/http://www.loaches.com/disease-treatment/levamisole-hydrochloride-1 |archive-date = 1 March 2009 }}</ref> Levamisole has been used to treat small ruminant animals since the late 1960s.<ref>{{cite journal | vauthors = Harder A | title = Chemotherapeutic approaches to nematodes: current knowledge and outlook | journal = Parasitology Research | volume = 88 | issue = 3 | pages = 272–277 | date = March 2002 | pmid = 11954915 | doi = 10.1007/s00436-001-0535-x }}</ref> Levamisole-resistant parasitic worms are common in sheep farms in New Zealand,<ref>{{cite journal | vauthors = Waghorn TS, Leathwick DM, Rhodes AP, Lawrence KE, Jackson R, Pomroy WE, West DM, Moffat JR | title = Prevalence of anthelmintic resistance on sheep farms in New Zealand | journal = New Zealand Veterinary Journal | volume = 54 | issue = 6 | pages = 271–277 | date = December 2006 | pmid = 17151724 | doi = 10.1080/00480169.2006.36710 }}</ref> Uruguay,<ref>{{cite journal | vauthors = Nari A, Salles J, Gil A, Waller PJ, Hansen JW | title = The prevalence of anthelmintic resistance in nematode parasites of sheep in southern Latin America: Uruguay | journal = Veterinary Parasitology | volume = 62 | issue = 3–4 | pages = 213–222 | date = April 1996 | pmid = 8686167 | doi = 10.1016/0304-4017(95)00908-6 }}</ref> Paraguay,<ref>{{cite journal | vauthors = Maciel S, Giménez AM, Gaona C, Waller PJ, Hansen JW | title = The prevalence of anthelmintic resistance in nematode parasites of sheep in southern Latin America: Paraguay | journal = Veterinary Parasitology | volume = 62 | issue = 3–4 | pages = 207–212 | date = April 1996 | pmid = 8686166 | doi = 10.1016/0304-4017(95)00907-8 }}</ref> and Brazil.<ref>{{cite journal | vauthors = Echevarria F, Borba MF, Pinheiro AC, Waller PJ, Hansen JW | title = The prevalence of anthelmintic resistance in nematode parasites of sheep in southern Latin America: Brazil | journal = Veterinary Parasitology | volume = 62 | issue = 3–4 | pages = 199–206 | date = April 1996 | pmid = 8686165 | doi = 10.1016/0304-4017(95)00906-x }}</ref>

===Other===
Levamisole has been used to treat a variety of dermatologic conditions, including skin infections, ], ], ], and ]s.<ref>{{cite journal | vauthors = Scheinfeld N, Rosenberg JD, Weinberg JM | title = Levamisole in dermatology : a review | journal = American Journal of Clinical Dermatology | volume = 5 | issue = 2 | pages = 97–104 | year = 2004 | pmid = 15109274 | doi = 10.2165/00128071-200405020-00004 | s2cid = 1171779 }}</ref>

An interesting side effect these reviewers reported in passing was "neurologic excitement". Later papers, from the Janssen group and others, indicate levamisole and its enantiomer, dexamisole, have some mood-elevating or ] properties, although this was never a marketed use of the drug.<ref>{{cite journal | vauthors = Vanhoutte PM, Van Nueten JM, Verbeuren TJ, Laduron PM | title = Differential effects of the isomers of tetramisole on adrenergic neurotransmission in cutaneous veins of dog | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 200 | issue = 1 | pages = 127–40 | date = January 1977 | pmid = 189006 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=189006 }}</ref><ref>{{cite journal | vauthors = Przegaliński E, Bigajska K, Siwanowicz J | title = Psychopharmacological profile of dexamisole | journal = Polish Journal of Pharmacology and Pharmacy | volume = 32 | issue = 1 | pages = 21–9 | year = 1980 | pmid = 7454609 }}</ref>

== Adverse effects ==
One of the more serious side effects of levamisole is ], or the depletion of the white blood cells. In particular, neutrophils appear to be affected the most. This occurs in 0.08–5% of the studied populations.<ref>{{cite web |title=Levamisole |url=http://www.deadiversion.usdoj.gov/drug_chem_info/levamisole.pdf |publisher=DEA |access-date=21 April 2014 |url-status=live |archive-url=https://web.archive.org/web/20131017084451/http://www.deadiversion.usdoj.gov/drug_chem_info/levamisole.pdf |archive-date=17 October 2013}}</ref>

It has been used as an ] in ], resulting in serious side effects that present as ], in which ] painful ]s can appear almost anywhere on skin.<ref name="mmwr">{{cite journal | title = Agranulocytosis associated with cocaine use - four States, March 2008-November 2009 | journal = MMWR. Morbidity and Mortality Weekly Report | volume = 58 | issue = 49 | pages = 1381–5 | date = December 2009 | pmid = 20019655 | url = https://www.cdc.gov/mmwr/preview/mmwrhtml/mm5849a3.htm | author1 = Centers for Disease Control Prevention (CDC) }}</ref><ref>{{cite journal | vauthors = Chang A, Osterloh J, Thomas J | title = Levamisole: a dangerous new cocaine adulterant | journal = Clinical Pharmacology and Therapeutics | volume = 88 | issue = 3 | pages = 408–11 | date = September 2010 | pmid = 20668440 | doi = 10.1038/clpt.2010.156 | s2cid = 31414939 }}</ref><ref>{{cite web |title=Cocaine powder: review of its prevalence, patterns of use and harm |url=https://www.gov.uk/government/publications/cocaine-powder-review-of-its-prevalence-patterns-of-use-and-harm |date=12 March 2015 |publisher=Advisory Council on the Misuse of Drugs }}</ref>

== Metabolism ==
Levamisole is readily absorbed from the gastrointestinal tract and metabolized in the liver. Its time to peak plasma concentration is 1.5–2 hours. The plasma elimination half-life is fairly quick at 3–4 hours which can contribute to not detecting levamisole intoxication. The metabolite half-life is 16 hours. Levamisole's excretion is primarily through the kidneys, with about 70% being excreted over 3 days. Only about 5% is excreted as unchanged levamisole.<ref>{{cite journal | vauthors = Kouassi E, Caillé G, Léry L, Larivière L, Vézina M | title = Novel assay and pharmacokinetics of levamisole and p-hydroxylevamisole in human plasma and urine | journal = Biopharmaceutics & Drug Disposition | volume = 7 | issue = 1 | pages = 71–89 | year = 1986 | pmid = 3754161 | doi = 10.1002/bdd.2510070110 }}</ref><ref>{{cite journal | vauthors = Luyckx M, Rousseau F, Cazin M, Brunet C, Cazin JC, Haguenoer JM, Devulder B, Lesieur I, Lesieur D, Gosselin P, Adenis L, Cappelaere P, Demaille A | title = Pharmacokinetics of levamisole in healthy subjects and cancer patients | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 7 | issue = 4 | pages = 247–54 | year = 1982 | pmid = 7166176 | doi = 10.1007/bf03189626 | s2cid = 13206196 }}</ref>

Drug testing of racehorse urine has led to the revelation that among levamisole equine metabolites are both ] and ], stimulants that are forbidden by racing authorities.<ref>{{cite journal | vauthors = Gutierrez J, Eisenberg RL, Koval NJ, Armstrong ER, Tharappel J, Hughes CG, Tobin T | title = Pemoline and tetramisole 'positives' in english racehorses following levamisole administration | journal = Irish Veterinary Journal | volume = 63 | issue = 8 | pages = 498 | date = August 2010 | pmid = 21777496 | pmc = 4177197 | doi = 10.1186/2046-0481-63-8-498 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Ho EN, Leung DK, Leung GN, Wan TS, Wong AS, Wong CH, Soma LR, Rudy JA, Uboh C, Sams R | title = Aminorex and rexamino as metabolites of levamisole in the horse | journal = Analytica Chimica Acta | volume = 638 | issue = 1 | pages = 58–68 | date = April 2009 | pmid = 19298880 | doi = 10.1016/j.aca.2009.02.033 | bibcode = 2009AcAC..638...58H }}</ref><ref>{{cite book | vauthors = Scarth, etal | chapter = The use of ''in vitro'' drug metabolism studies to complement, reduce and refine ''in vivo'' administrations in medication and doping control. | veditors = Beresford GD, Howitt RG |title=Proceedings of the 18th International Conference of Racing analysts and Veterinarians (ICRAV), Queenstown, New Zealand |date=2012 |publisher=Dumnor Publishing, Limited |location=Auckland |isbn=978-0-473-22084-6 | pages = 213–222 }}</ref> Further testing confirmed aminorex in human and canine urine, meaning that both humans and dogs also metabolize levamisole into aminorex,<ref name="pmid21531521">{{cite journal | vauthors = Bertol E, Mari F, Milia MG, Politi L, Furlanetto S, Karch SB | title = Determination of aminorex in human urine samples by GC-MS after use of levamisole | journal = Journal of Pharmaceutical and Biomedical Analysis | volume = 55 | issue = 5 | pages = 1186–1189 | date = July 2011 | pmid = 21531521 | doi = 10.1016/j.jpba.2011.03.039 }}</ref> though it is unclear whether plasma aminorex is present at any appreciable level. Blood samples following oral administration of levamisole out to 172 hr post-dose did not demonstrate any plasma aminorex levels above that of the limit of quantification (LoQ). Additionally, in cocaine-positive plasma samples, of which 42% contained levamisole, aminorex was never reported at concentrations higher than LoQ.<ref>{{cite journal | vauthors = Hess C, Ritke N, Broecker S, Madea B, Musshoff F | title = Metabolism of levamisole and kinetics of levamisole and aminorex in urine by means of LC-QTOF-HRMS and LC-QqQ-MS | journal = Analytical and Bioanalytical Chemistry | volume = 405 | issue = 12 | pages = 4077–4088 | date = May 2013 | pmid = 23436169 | doi = 10.1007/s00216-013-6829-x | s2cid = 2222462 }}</ref>

==Detection in body fluids==
Levamisole may be quantified in blood, plasma, or urine as a diagnostic tool in clinical poisoning situations or to aid in the medicolegal investigation of suspicious deaths involving adulterated street drugs. About 3% of an oral dose is eliminated unchanged in the 24-hour urine of humans. A post mortem blood levamisole concentration of 2.2&nbsp;mg/L was present in a woman who died of a cocaine overdose.<ref>{{cite journal | vauthors = Vandamme TF, Demoustier M, Rollmann B | title = Quantitation of levamisole in plasma using high performance liquid chromatography | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 20 | issue = 2 | pages = 145–9 | year = 1995 | pmid = 8582440 | doi = 10.1007/bf03226369 | s2cid = 9258640 }}</ref><ref>{{cite book | vauthors = Baselt R | title = Disposition of Toxic Drugs and Chemicals in Man | edition = 9th | publisher = Biomedical Publications | location = Seal Beach, CA | date = 2011 | pages = 901–902 | url= http://www.biomedicalpublications.com/levamisole.pdf |access-date=22 January 2011 |url-status=dead |archive-url= https://web.archive.org/web/20110910160556/http://www.biomedicalpublications.com/levamisole.pdf |archive-date=10 September 2011 }}</ref>

== Adulterant in illegal drugs ==
Levamisole has increasingly been used as a ] in ] sold around the globe with the highest incidence being in the United States. In 2008–2009, levamisole was found in 69% of cocaine samples seized by the ] (DEA).<ref name="mmwr"/> By April 2011, the DEA reported the adulterant was found in 82% of seizures.<ref name="abc20110623">{{cite news | vauthors = Moisse K | title = Cocaine Laced With Veterinary Drug Levamisole Eats Away at Flesh | date = 23 June 2011 | url = https://abcnews.go.com/Health/Wellness/flesh-eating-cocaine-laced-veterinary-drug-levamisole/story?id=13902353 | work = ABC News | access-date = 23 June 2011 | url-status = live | archive-url = https://web.archive.org/web/20110625225534/https://abcnews.go.com/Health/Wellness/flesh-eating-cocaine-laced-veterinary-drug-levamisole/story?id=13902353 | archive-date = 25 June 2011 }}</ref>

Levamisole adds bulk and weight to powdered ] (whereas other adulterants produce smaller "rocks" of cocaine) and makes the drug appear purer.<ref>{{cite news|url=https://news.yahoo.com/s/hsn/contaminatedcocainecancausefleshtorot;_ylt=Arpc.e2vZk4K0VyhIadneKes0NUE;_ylu=X3oDMTRhMzAybmR2BGFzc2V0A2hzbi8yMDEwMDYwMS9jb250YW1pbmF0ZWRjb2NhaW5lY2FuY2F1c2VmbGVzaHRvcm90BGNjb2RlA21vc3Rwb3B1bGFyBGNwb3MDOARwb3MDNQRwdANob21lX2Nva2UEc2VjA3luX2hlYWRsaW5lX2xpc3QEc2xrA2NvbnRhbWluYXRlZA--|title=Contaminated Cocaine Can Cause Flesh to Rot| vauthors = Doheny K |date=1 June 2010|work=]|access-date=8 June 2010|url-status=dead|archive-url=https://web.archive.org/web/20100607071126/http://news.yahoo.com/s/hsn/contaminatedcocainecancausefleshtorot|archive-date=7 June 2010}}</ref> In a series of investigative articles for '']'', Brendan Kiley details other rationales for levamisole's rise as an adulterant: possible stimulant effects, a similar appearance to cocaine, and an ability to pass street purity tests.<ref name=kiley>{{cite news |title=The Mystery of the Tainted Cocaine | vauthors = Kiley B |url=http://www.thestranger.com/seattle/the-mystery-of-the-tainted-cocaine/Content?oid=4683741 |work=] |date=17 August 2010 |access-date=21 December 2010 |url-status=live |archive-url=https://web.archive.org/web/20101211143437/http://www.thestranger.com/seattle/the-mystery-of-the-tainted-cocaine/Content?oid=4683741 |archive-date=11 December 2010 }}</ref>

Levamisole suppresses the production of ]s, resulting in ] and ]. With the increasing use of levamisole as an ], a number of these complications have been reported among cocaine users.<ref name="mmwr"/><ref name="annals">{{cite journal | vauthors = Zhu NY, Legatt DF, Turner AR | title = Agranulocytosis after consumption of cocaine adulterated with levamisole | journal = Annals of Internal Medicine | volume = 150 | issue = 4 | pages = 287–289 | date = February 2009 | pmid = 19153405 | doi = 10.7326/0003-4819-150-4-200902170-00102 }}</ref><ref>{{cite journal | vauthors = Kinzie E | title = Levamisole found in patients using cocaine | journal = Annals of Emergency Medicine | volume = 53 | issue = 4 | pages = 546–547 | date = April 2009 | pmid = 19303517 | doi = 10.1016/j.annemergmed.2008.10.017 | doi-access = free }}</ref> Levamisole has also been linked to a risk of ],<ref>{{cite journal | vauthors = Menni S, Pistritto G, Gianotti R, Ghio L, Edefonti A | title = Ear lobe bilateral necrosis by levamisole-induced occlusive vasculitis in a pediatric patient | journal = Pediatric Dermatology | volume = 14 | issue = 6 | pages = 477–479 | year = 1997 | pmid = 9436850 | doi = 10.1111/j.1525-1470.1997.tb00695.x | s2cid = 26527277 }}</ref> and two cases of vasculitic skin necrosis have been reported in users of cocaine adulterated with levamisole.<ref>{{cite journal | vauthors = Bradford M, Rosenberg B, Moreno J, Dumyati G | title = Bilateral necrosis of earlobes and cheeks: another complication of cocaine contaminated with levamisole | journal = Annals of Internal Medicine | volume = 152 | issue = 11 | pages = 758–759 | date = June 2010 | pmid = 20513844 | doi = 10.7326/0003-4819-152-11-201006010-00026 | doi-access = free }}</ref>

Levamisole-tainted cocaine has caused three deaths and sickened over 100 in US and Canada, as of 2009.<ref>{{Cite web | vauthors = Johnston D |date= 31 August 2009 |title=Tainted cocaine kills 3, sickens dozens|url=https://www.nbcnews.com/id/wbna32633293|access-date=31 August 2020|website=msnbc.com|language=en}}</ref>

==Chemistry==
The original synthesis at Janssen Pharmaceutica resulted in the preparation of a ] of two ], whose hydrochloride salt was reported to have a melting point of 264–265&nbsp;°C; the free base of the racemate has a melting point of 87–89&nbsp;°C. The racemic mixture is referred to as "tetramisole" - levamisole refers only to the levorotatory enantiomer of tetramisole.{{cn|date=December 2022}}

==Toxicity==
The ] (intravenous, mouse) is 22&nbsp;mg/kg.<ref name = Sym>{{cite book | vauthors = Symoens J, DeCree J, Bever WV, Janssen PA | chapter = Levamisole | date = 1979 | title = Pharmacological and Biochemical Properties of Drug Substances | volume = 2 | veditors = Goldberg ME | pages = 407–464 | location = Washington | publisher = American Pharmaceutical Association | oclc = 1106595378 }}</ref>

== Laboratory use ==
Levamisole ] and ] most ]s of ] (e.g., human liver, bone, kidney, and spleen) except the intestinal and placental isoform.<ref name="pmid6169">{{cite journal | vauthors = Van Belle H | title = Alkaline phosphatase. I. Kinetics and inhibition by levamisole of purified isoenzymes from humans | journal = Clinical Chemistry | volume = 22 | issue = 7 | pages = 972–6 | date = July 1976 | doi = 10.1093/clinchem/22.7.972 | pmid = 6169| doi-access = free }}</ref><ref>{{cite journal|title=Levamisole inhibition of alkaline phosphatase and 5'-nucleotidase of bovine milk fat globule membranes|journal=International Journal of Biochemistry|vauthors=Khodaparast-Sharifi SH, Snow LD|year=1989|volume=21|issue=4|pages=401–405|doi=10.1016/0020-711X(89)90364-9|pmid=2545478}}</ref> It is thus used as an inhibitor along with substrate to reduce background alkaline phosphatase activity in biomedical assays involving detection signal amplification by intestinal alkaline phosphatase, for example in ] or ] protocols.{{cn|date=December 2022}}

It is used to immobilize the nematode '']'' on glass slides for imaging and dissection.<ref>{{cite web |url=http://genetics.wustl.edu/tslab/protocols/dissection-staining-in-situ/gonad-dissections/ |title=Gonad Dissections &#124; Schedl Lab |access-date=15 May 2014 |url-status=live |archive-url=https://web.archive.org/web/20140517154147/http://genetics.wustl.edu/tslab/protocols/dissection-staining-in-situ/gonad-dissections/ |archive-date=17 May 2014 }} Schedl Lab Protocol for gonad dissections</ref>

In a ''C. elegans'' behavioral assay, analyzing the time course of paralysis provides information about the neuromuscular junction. Levamisole acts as an acetylcholine receptor agonist, which leads to muscle contraction. Continuing activation leads to paralysis. The time course of paralysis provides information about the acetylcholine receptors on the muscle. For example, mutants with fewer acetylcholine receptors may paralyze slower than wild type.<ref>{{cite journal | vauthors = Rand JB | title = Acetylcholine | journal = WormBook | pages = 1–21 | date = January 2007 | pmid = 18050502 | pmc = 4781110 | doi = 10.1895/wormbook.1.131.1 | url = https://www.ncbi.nlm.nih.gov/books/NBK19736/ }}</ref>

==Research==
It has been studied as a method to stimulate the immune system as part of the treatment of ].<ref>{{cite journal | vauthors = Dillman RO | title = Cancer immunotherapy | journal = Cancer Biotherapy & Radiopharmaceuticals | volume = 26 | issue = 1 | pages = 1–64 | date = February 2011 | pmid = 21355777 | doi = 10.1089/cbr.2010.0902 }}</ref> It has also shown some efficacy in the treatment of ] in children.<ref>{{cite journal | vauthors = Couderc A, Bérard E, Guigonis V, Vrillon I, Hogan J, Audard V, Baudouin V, Dossier C, Boyer O | title = | journal = Archives de Pédiatrie | volume = 24 | issue = 12 | pages = 1312–1320 | date = December 2017 | pmid = 29146214 | doi = 10.1016/j.arcped.2017.09.002 }}</ref>

After being pulled from the market in the US and Canada in 1999 and 2003, respectively, levamisole has been tested in combination with ] to treat ]. Evidence from ]s support its addition to fluorouracil therapy to benefit patients with colon cancer. In some of the leukemic cell line studies, both levamisole and ] showed similar effect.<ref>(Chirigos et al. (1969, 1973, 1975)).</ref>

== Veterinary uses ==
The combination ]/levamisole, sold under the brand name Valcor, is ] for the treatment and control of gastrointestinal roundworms, lungworms, grubs, sucking lice, and mange mites in cattle.<ref name="Valcor FDA label">{{cite web | title=Animal Drugs @ FDA | website=animaldrugsatfda.fda.gov | url=https://animaldrugsatfda.fda.gov/adafda/views/#/home/previewsearch/141-553 | access-date=25 January 2023}}</ref> It is given by ] injection.<ref name="Valcor FDA label" />

== References ==
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{{Anthelmintics}}
{{Nicotinic acetylcholine receptor modulators}}
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