Difference between revisions of "Levamisole"

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'''Levamisole''' (marketed as the [[hydrochloride]] salt under the trade name '''Ergamisol''') is an [[anthelminthic]] and [[immunomodulator]] belonging to a class of synthetic [[imidazothiazole]] derivatives. It was discovered at [[Janssen Pharmaceutica]] in 1966. Levamisole has been used in humans to treat [[parasitic worm]] infections, and has been studied in combination with other forms of [[chemotherapy]] for [[colon cancer]], [[melanoma]], and [[head and neck cancer]]. The drug was withdrawn from the U.S. and Canadian markets in 2000 and 2003 respectively, due to the risk of serious side effects and the availability of more effective replacement medications.<ref>{{cite news |url=http://findarticles.com/p/articles/mi_m3374/is_18_22/ai_68536218/ |title=Janssen discontinues Ergamisol |last=Frederick |first=James |work=Drug Store News |date=November 27, 2000 |accessdate=2009-08-13}}</ref><ref>{{cite web |url=http://www.pharmacists.ca/content/hcp/tools/drugnews/discontinued.htm |title=Products Discontinued from the Market Since Publication of the 2000 CPS |publisher=Canadian Pharmacists Association |accessdate=2009-08-13}}</ref>
 
'''Levamisole''' (marketed as the [[hydrochloride]] salt under the trade name '''Ergamisol''') is an [[anthelminthic]] and [[immunomodulator]] belonging to a class of synthetic [[imidazothiazole]] derivatives. It was discovered at [[Janssen Pharmaceutica]] in 1966. Levamisole has been used in humans to treat [[parasitic worm]] infections, and has been studied in combination with other forms of [[chemotherapy]] for [[colon cancer]], [[melanoma]], and [[head and neck cancer]]. The drug was withdrawn from the U.S. and Canadian markets in 2000 and 2003 respectively, due to the risk of serious side effects and the availability of more effective replacement medications.<ref>{{cite news |url=http://findarticles.com/p/articles/mi_m3374/is_18_22/ai_68536218/ |title=Janssen discontinues Ergamisol |last=Frederick |first=James |work=Drug Store News |date=November 27, 2000 |accessdate=2009-08-13}}</ref><ref>{{cite web |url=http://www.pharmacists.ca/content/hcp/tools/drugnews/discontinued.htm |title=Products Discontinued from the Market Since Publication of the 2000 CPS |publisher=Canadian Pharmacists Association |accessdate=2009-08-13}}</ref>
  
−
Currently, levamisole remains in [[veterinary medicine|veterinary]] use as a [[dewormer]] for livestock. The medication has also been increasingly used as an [[adulterant]] in [[cocaine]] sold in the US and Canada, resulting in serious side effects.<ref name="mmwr">{{cite journal |author= |title=Agranulocytosis associated with cocaine use - four States, March 2008-November 2009 |journal=MMWR Morb. Mortal. Wkly. Rep. |volume=58 |issue=49 |pages=1381–5 |year=2009 |month=December |pmid=20019655 |doi= |url=http://www.cdc.gov/mmwr/preview/mmwrhtml/mm5849a3.htm}}</ref>
+
Currently, levamisole remains in [[veterinary medicine|veterinary]] use as a [[dewormer]] for livestock. The medication has also been increasingly used as an [[adulterant]] in [[cocaine]] sold in the US and Canada, resulting in serious side effects.<ref name="mmwr">{{cite journal |author= |title=Agranulocytosis associated with cocaine use - four States, March 2008-November 2009 |journal=MMWR Morb. Mortal. Wkly. Rep. |volume=58 |issue=49 |pages=1381–5 |year=2009 |month=December |pmid=20019655 |doi= |url=http://www.cdc.gov/mmwr/preview/mmwrhtml/mm5849a3.htm |author1= Centers for Disease Control and Prevention (CDC)}}</ref>
  
 
==Clinical use==
 
==Clinical use==
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It is also used routinely in [[India]] to treat [[steroid]] dependent childhood [[nephrotic syndrome]] cases, which is probably based on literature published in a few UK based studies.<ref name="pmid1675705">{{cite journal |author= |title=Levamisole for corticosteroid-dependent nephrotic syndrome in childhood. British Association for Paediatric Nephrology |journal=Lancet |volume=337 |issue=8757 |pages=1555–7 |year=1991 |pmid=1675705 |doi=}}</ref>
 
It is also used routinely in [[India]] to treat [[steroid]] dependent childhood [[nephrotic syndrome]] cases, which is probably based on literature published in a few UK based studies.<ref name="pmid1675705">{{cite journal |author= |title=Levamisole for corticosteroid-dependent nephrotic syndrome in childhood. British Association for Paediatric Nephrology |journal=Lancet |volume=337 |issue=8757 |pages=1555–7 |year=1991 |pmid=1675705 |doi=}}</ref>
 +
In dermatologic disease levamisole has been successfully used in the treatment of parasitic, viral and bacterial infections including leprosy, collagen vascular diseases, inflammatory skin diseases and children with impaired immune a variety of reasons. It has also been used in combination with other drugs for treating a number of dermatologic disorders, e.g. in combination with cimetidine for treating recalcitrant warts, with prednisolone for treating lichen planus, erythema multiforme and aphthous ulcers of the mouth.<ref>Scheinfeld N, Rosenberg JD, Weinberg JM. Levamisole in dermatology: a review. Am J Clin Dermatol. 2004;5:97-104. "PMID 15109274"</ref>
  
 
==Laboratory use==
 
==Laboratory use==
Line 59: Line 60:
 
Levamisole has increasingly been used as a [[cutting agent]] in [[cocaine]] sold in the US and Canada. In 2008&ndash;2009, levamisole was found in 69% of cocaine samples seized by the [[Drug Enforcement Administration|US Drug Enforcement Administration]].<ref name="mmwr"/> Levamisole adds bulk and weight to powdered [[cocaine]] (whereas other adulterants will produce smaller "rocks" of cocaine) and makes the drug appear more pure<ref>{{cite news|url=http://news.yahoo.com/s/hsn/contaminatedcocainecancausefleshtorot;_ylt=Arpc.e2vZk4K0VyhIadneKes0NUE;_ylu=X3oDMTRhMzAybmR2BGFzc2V0A2hzbi8yMDEwMDYwMS9jb250YW1pbmF0ZWRjb2NhaW5lY2FuY2F1c2VmbGVzaHRvcm90BGNjb2RlA21vc3Rwb3B1bGFyBGNwb3MDOARwb3MDNQRwdANob21lX2Nva2UEc2VjA3luX2hlYWRsaW5lX2xpc3QEc2xrA2NvbnRhbWluYXRlZA--|title=Contaminated Cocaine Can Cause Flesh to Rot|last=Doheny|first=Kathleen|date=Jun 1 2010|work=[[Yahoo!]]|accessdate=8 June 2010|postscript=.}}</ref>
 
Levamisole has increasingly been used as a [[cutting agent]] in [[cocaine]] sold in the US and Canada. In 2008&ndash;2009, levamisole was found in 69% of cocaine samples seized by the [[Drug Enforcement Administration|US Drug Enforcement Administration]].<ref name="mmwr"/> Levamisole adds bulk and weight to powdered [[cocaine]] (whereas other adulterants will produce smaller "rocks" of cocaine) and makes the drug appear more pure<ref>{{cite news|url=http://news.yahoo.com/s/hsn/contaminatedcocainecancausefleshtorot;_ylt=Arpc.e2vZk4K0VyhIadneKes0NUE;_ylu=X3oDMTRhMzAybmR2BGFzc2V0A2hzbi8yMDEwMDYwMS9jb250YW1pbmF0ZWRjb2NhaW5lY2FuY2F1c2VmbGVzaHRvcm90BGNjb2RlA21vc3Rwb3B1bGFyBGNwb3MDOARwb3MDNQRwdANob21lX2Nva2UEc2VjA3luX2hlYWRsaW5lX2xpc3QEc2xrA2NvbnRhbWluYXRlZA--|title=Contaminated Cocaine Can Cause Flesh to Rot|last=Doheny|first=Kathleen|date=Jun 1 2010|work=[[Yahoo!]]|accessdate=8 June 2010|postscript=.}}</ref>
  
−
Levamsiole is known to suppress the production of [[white blood cell]]s, resulting in [[neutropenia]] and [[agranulocytosis]]. With the increasing use of levamisole as an [[adulterant]], a number of cases of these complications have been reported among cocaine users.<ref name="mmwr"/><ref name="annals">{{cite journal | author=Nancy Y Zhu, Donald F. LeGatt, A Robert Turner | title=Agranulocytosis After Consumption of Cocaine Adulterated With Levamisole | url=http://www.annals.org/cgi/content/short/150/4/287 | journal=[[Annals of Internal Medicine]] | volume=150 | issue=4 | month=February| year=2009 | accessdate=2009-10-07 | pages=287–289}}</ref><ref>{{cite journal | url=http://www.mdconsult.com/das/article/body/154945316-2/jorg=journal&source=&sp=21877276&sid=0/N/691072/1.html?issn=01960644 | title=Levamisole Found in Patients Using Cocaine | journal=[[Annals of Emergency Medicine]] | volume=53 | issue=4 | month=April | year=2009 | first=Erik | last=Kinzie | accessdate=2009-08-18 | doi=10.1016/j.annemergmed.2008.10.017 | pages=546}}</ref> Levamisole has also been linked to a risk of [[vasculitis]],<ref>{{cite journal |author=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=Pediatr Dermatol |volume=14 |issue=6 |pages=477–9 |year=1997 |pmid=9436850 |doi= |url=}}</ref> and 2 cases of vasculitic skin necrosis have been reported in users of cocaine adulterated with levamisole.<ref>{{cite journal |author=Bradford M, Rosenberg B, Moreno J, Dumyati G |title=Bilateral necrosis of earlobes and cheeks: another complication of cocaine contaminated with levamisole |journal=Ann. Intern. Med. |volume=152 |issue=11 |pages=758–9 |year=2010 |month=June |pmid=20513844 |doi=10.1059/0003-4819-152-11-201006010-00026 |url=}}</ref> Toxicology reports showed that levamisole, along with cocaine, was present in [[DJ AM|DJ AM's]] body at the time of his death.<ref>http://www.sfgate.com/cgi-bin/article.cgi?f=/n/a/2009/09/29/national/a075802D66.DTL&tsp=1</ref>{{dead link|date=June 2010}} Andrew Koppel, son of newsman Ted Koppel, was also found with Levamisole in his body after his death was ruled a drug overdose.<ref>http://www.nydailynews.com/ny_local/2010/06/19/2010-06-19_koppel_son_cocktail_drug_death_an_accident.html</ref>
+
Levamsiole is known to suppress the production of [[white blood cell]]s, resulting in [[neutropenia]] and [[agranulocytosis]]. With the increasing use of levamisole as an [[adulterant]], a number of cases of these complications have been reported among cocaine users.<ref name="mmwr"/><ref name="annals">{{cite journal | author=Nancy Y Zhu, Donald F. LeGatt, A Robert Turner | title=Agranulocytosis After Consumption of Cocaine Adulterated With Levamisole | url=http://www.annals.org/cgi/content/short/150/4/287 | journal=[[Annals of Internal Medicine]] | volume=150 | issue=4 | month=February| year=2009 | accessdate=2009-10-07 | pages=287–289 | pmid=19153405 | doi=10.1059/0003-4819-150-4-200902170-00102}}</ref><ref>{{cite journal | url=http://www.mdconsult.com/das/article/body/154945316-2/jorg=journal&source=&sp=21877276&sid=0/N/691072/1.html?issn=01960644 | title=Levamisole Found in Patients Using Cocaine | journal=[[Annals of Emergency Medicine]] | volume=53 | issue=4 | month=April | year=2009 | first=Erik | last=Kinzie | accessdate=2009-08-18 | doi=10.1016/j.annemergmed.2008.10.017 | pages=546 | pmid=19303517}}</ref> Levamisole has also been linked to a risk of [[vasculitis]],<ref>{{cite journal |author=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=Pediatr Dermatol |volume=14 |issue=6 |pages=477–9 |year=1997 |pmid=9436850 |doi= 10.1111/j.1525-1470.1997.tb00695.x|url=}}</ref> and 2 cases of vasculitic skin necrosis have been reported in users of cocaine adulterated with levamisole.<ref>{{cite journal |author=Bradford M, Rosenberg B, Moreno J, Dumyati G |title=Bilateral necrosis of earlobes and cheeks: another complication of cocaine contaminated with levamisole |journal=Ann. Intern. Med. |volume=152 |issue=11 |pages=758–9 |year=2010 |month=June |pmid=20513844 |doi=10.1059/0003-4819-152-11-201006010-00026 |url=}}</ref> Toxicology reports showed that levamisole, along with cocaine, was present in [[DJ AM|DJ AM's]] body at the time of his death.<ref>{{cite news| url=http://www.sfgate.com/cgi-bin/article.cgi?f=/n/a/2009/09/29/national/a075802D66.DTL&tsp=1 | work=The San Francisco Chronicle}} {{Dead link|date=August 2010|bot=RjwilmsiBot}}</ref>{{dead link|date=June 2010}} Andrew Koppel, son of newsman Ted Koppel, was also found with Levamisole in his body after his death was ruled a drug overdose.<ref>http://www.nydailynews.com/ny_local/2010/06/19/2010-06-19_koppel_son_cocktail_drug_death_an_accident.html</ref>
  
 
==References==
 
==References==
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[[de:Levamisol]]
 
[[de:Levamisol]]
 
[[fa:لوامیزول]]
 
[[fa:لوامیزول]]
 +
[[it:Levamisolo]]
 
[[ja:レバミゾール]]
 
[[ja:レバミゾール]]
 
[[pt:Levamisol]]
 
[[pt:Levamisol]]
 
[[ru:Левамизол]]
 
[[ru:Левамизол]]
−
[[sk:Levamizol]]
 
 
[[zh:左旋咪唑]]
 
[[zh:左旋咪唑]]
 
[[Category:2Fix]]
 
[[Category:2Fix]]

Latest revision as of 15:42, 27 September 2010

Levamisole
200px
Systematic (IUPAC) name
(S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole
Clinical data
Routes of
administration		 Oral
Pharmacokinetic data
Metabolism Hepatic
Biological half-life 4.4-5.6 hours (biphasic)
Identifiers
CAS Number 14769-73-4
ATC code P02CE01 (WHO) QP52AE01
PubChem CID 26879
DrugBank APRD01067
Chemical data
Formula C11H12N2S
Molar mass 204.292 g/mol[[Script error: No such module "String".]]
Physical data
Density 1.31 g/cm3
Melting point 230 °C (446 °F)
  (verify)
Script error: No such module "TemplatePar".Expression error: Unexpected < operator.

Levamisole (marketed as the hydrochloride salt under the trade name Ergamisol) is an anthelminthic and immunomodulator belonging to a class of synthetic imidazothiazole derivatives. It was discovered at Janssen Pharmaceutica in 1966. Levamisole has been used in humans to treat parasitic worm infections, and has been studied in combination with other forms of chemotherapy for colon cancer, melanoma, and head and neck cancer. The drug was withdrawn from the U.S. and Canadian markets in 2000 and 2003 respectively, due to the risk of serious side effects and the availability of more effective replacement medications.[1][2]

Currently, levamisole remains in veterinary use as a dewormer for livestock. The medication has also been increasingly used as an adulterant in cocaine sold in the US and Canada, resulting in serious side effects.[3]

Clinical use

Levamisole was originally used as an antihelminthic to treat worm infestations in both humans and animals. Most current commercial preparations are intended for veterinary use as a dewormer in cattle, pigs, and sheep. However, levamisole has also gained prominence among aquarists as an effective treatment for Camallanus roundworm infestations in freshwater tropical fish.[4]

Levamisole has been tested in combination with fluorouracil to treat colon cancer. There is no good evidence from clinical trials that its addition to fluorouracil therapy benefits patients with colon cancer, and it is no longer used for this. It is also used infrequently to treat melanoma and head and neck cancer. It is unclear from its mechanism of action why it would have an effect in treating colon cancer, although it has been shown to have "immune-stimulating" properties in some situations.

A 1984 study on complicated influenza had found levamisole to be an effective inducer of interferon and had recommended its use in combination therapy for influenza.[5]

It is also used routinely in India to treat steroid dependent childhood nephrotic syndrome cases, which is probably based on literature published in a few UK based studies.[6] In dermatologic disease levamisole has been successfully used in the treatment of parasitic, viral and bacterial infections including leprosy, collagen vascular diseases, inflammatory skin diseases and children with impaired immune a variety of reasons. It has also been used in combination with other drugs for treating a number of dermatologic disorders, e.g. in combination with cimetidine for treating recalcitrant warts, with prednisolone for treating lichen planus, erythema multiforme and aphthous ulcers of the mouth.[7]

Laboratory use

Levamisole reversibly but non-competitively inhibits most isoforms of alkaline phosphatase (e.g. human liver, bone, kidney, and spleen) except the intestinal and placental isoform.[8] 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 in situ hybridization or Western blot protocols.

In addition, it is used to immobilize the nematode C. elegans on glass slides for imaging.

Illicit use

Levamisole has increasingly been used as a cutting agent in cocaine sold in the US and Canada. In 2008–2009, levamisole was found in 69% of cocaine samples seized by the US Drug Enforcement Administration.[3] Levamisole adds bulk and weight to powdered cocaine (whereas other adulterants will produce smaller "rocks" of cocaine) and makes the drug appear more pure[9]

Levamsiole is known to suppress the production of white blood cells, resulting in neutropenia and agranulocytosis. With the increasing use of levamisole as an adulterant, a number of cases of these complications have been reported among cocaine users.[3][10][11] Levamisole has also been linked to a risk of vasculitis,[12] and 2 cases of vasculitic skin necrosis have been reported in users of cocaine adulterated with levamisole.[13] Toxicology reports showed that levamisole, along with cocaine, was present in DJ AM's body at the time of his death.[14][dead link] Andrew Koppel, son of newsman Ted Koppel, was also found with Levamisole in his body after his death was ruled a drug overdose.[15]

References

Cite error: Invalid <references> tag; parameter "group" is allowed only.

Use <references />, or <references group="..." />
Antiplatyhelmintic agents
Binds tubulin
Other/unknown
Binds tubulin
Other/unknown
Antinematodal agents
(including
macrofilaricides)
Binds tubulin
Other/unknown
de:Levamisol

fa:لوامیزول it:Levamisolo ja:レバミゾール pt:Levamisol ru:Левамизол

zh:左旋咪唑
  1. ↑ Frederick, James (November 27, 2000). "Janssen discontinues Ergamisol". Drug Store News. Retrieved 2009-08-13. 
  2. ↑ "Products Discontinued from the Market Since Publication of the 2000 CPS". Canadian Pharmacists Association. Retrieved 2009-08-13. 
  3. ↑ 3.0 3.1 3.2 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  4. ↑ Sanford, Shari (2007). "Levamisole Hydrochloride: Its application and usage in freshwater aquariums". Loaches Online. Retrieved 2009-02-27. 
  5. ↑ Grishchenko SV, Lavrukhina LA, Ketiladze ES, Krylov VF, Ershov FI (1984). "[Results of combined therapy using levamisole for patients with influenza complicated by pneumonia]". Vopr. Virusol. (in Russian). 29 (2): 175–9. PMID 6203228. 
  6. ↑ "Levamisole for corticosteroid-dependent nephrotic syndrome in childhood. British Association for Paediatric Nephrology". Lancet. 337 (8757): 1555–7. 1991. PMID 1675705. 
  7. ↑ Scheinfeld N, Rosenberg JD, Weinberg JM. Levamisole in dermatology: a review. Am J Clin Dermatol. 2004;5:97-104. "PMID 15109274"
  8. ↑ Van Belle H (1976). "Alkaline phosphatase. I. Kinetics and inhibition by levamisole of purified isoenzymes from humans". Clin. Chem. 22 (7): 972–6. PMID 6169. 
  9. ↑ Doheny, Kathleen (Jun 1 2010). "Contaminated Cocaine Can Cause Flesh to Rot". Yahoo!. Retrieved 8 June 2010.  Check date values in: |date= (help)
  10. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  11. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  12. ↑ Menni S, Pistritto G, Gianotti R, Ghio L, Edefonti A (1997). "Ear lobe bilateral necrosis by levamisole-induced occlusive vasculitis in a pediatric patient". Pediatr Dermatol. 14 (6): 477–9. doi:10.1111/j.1525-1470.1997.tb00695.x. PMID 9436850. 
  13. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  14. ↑ The San Francisco Chronicle http://www.sfgate.com/cgi-bin/article.cgi?f=/n/a/2009/09/29/national/a075802D66.DTL&tsp=1.  Missing or empty |title= (help)[dead link]
  15. ↑ http://www.nydailynews.com/ny_local/2010/06/19/2010-06-19_koppel_son_cocktail_drug_death_an_accident.html
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