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===Weight-loss===
===Weight-loss===
Although often used by [[bodybuilder]]s during their "cutting" cycles,{{cn|date=June 2016}} the drug has been more recently known to the mainstream, particularly through publicized stories of use by celebrities such as [[Victoria Beckham]],<ref name="independent"/> [[Britney Spears]], and [[Lindsay Lohan]],
Although often used by [[bodybuilder]]s during their "cutting" cycles,<ref>{{cite web | url=https://www.steroidsandsarms.com/pct | title= Steroids and SARMS Handbook | access-date=2019-06-16}}</ref> the drug has been more recently known to the mainstream, particularly through publicized stories of use by celebrities such as [[Victoria Beckham]],<ref name="independent"/> [[Britney Spears]], and [[Lindsay Lohan]],
<ref>{{cite news | title=Clenbuterol Weight Loss Hollywood Secret | url=http://www.prbuzz.com/health-a-fitness/63324-clenbuterol-weight-loss-hollywood-secret.html#.UYFkZUqU5qM | work=PRBuzz | date=2012-05-17 | accessdate=2012-04-10 | location= London}}</ref> for its [[off-label use]] as a weight-loss drug similar to usage of other sympathomimetic amines such as [[ephedrine]], despite the lack of sufficient clinical testing either supporting or negating such use.
<ref>{{cite news | title=Clenbuterol Weight Loss Hollywood Secret | url=http://www.prbuzz.com/health-a-fitness/63324-clenbuterol-weight-loss-hollywood-secret.html#.UYFkZUqU5qM | work=PRBuzz | date=2012-05-17 | accessdate=2012-04-10 | location= London}}</ref> for its [[off-label use]] as a weight-loss drug similar to usage of other sympathomimetic amines such as [[ephedrine]], despite the lack of sufficient clinical testing either supporting or negating such use.


Revision as of 13:35, 16 June 2019

Clenbuterol
Clenbuterol (top),
and (R)-(−)-clenbuterol (bottom)
Clinical data
Trade namesDilaterol, Spiropent, Ventipulmin, others[1]
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • C
Routes of
administration		Oral (tablets, oral solution)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability89–98% (orally)
MetabolismHepatic (negligible)
Elimination half-life36–48 hours
ExcretionFeces and urine
Identifiers
  • (RS)-1-(4-Amino-3,5-dichlorophenyl)-2-(tert-butylamino)ethan-1-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.048.499 Edit this at Wikidata
Chemical and physical data
FormulaC12H18Cl2N2O
Molar mass277.19 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • Clc1cc(cc(Cl)c1N)C(O)CNC(C)(C)C
  • InChI=1S/C12H18Cl2N2O/c1-12(2,3)16-6-10(17)7-4-8(13)11(15)9(14)5-7/h4-5,10,16-17H,6,15H2,1-3H3 checkY
  • Key:STJMRWALKKWQGH-UHFFFAOYSA-N checkY
  (verify)

Clenbuterol is a sympathomimetic amine used by sufferers of breathing disorders as a decongestant and bronchodilator. People with chronic breathing disorders such as asthma use this as a bronchodilator to make breathing easier. It is most commonly available as the hydrochloride salt, clenbuterol hydrochloride.[2]

It was patented in 1967 and came into medical use in 1977.[3]

Medical uses

Clenbuterol is approved for use in some countries as a bronchodilator for asthma.

Clenbuterol is a β2 agonist with some structural and pharmacological similarities to epinephrine and salbutamol, but its effects are more potent and longer-lasting as a stimulant and thermogenic drug.[citation needed] It is commonly used for smooth muscle-relaxant properties as a bronchodilator and tocolytic.

It is classified by the World Athletic Doping Association as an anabolic agent, not as a β2 agonist.[4]

Clenbuterol is also prescribed for treatment of respiratory diseases for horses, and not in dogs and cats; it is illegal in most countries to use in livestock used for food.[5]

Side effects

Clenbuterol can cause these side effects:[6]

Overdosage

Use over the recommended dose of about 120 μg can cause muscle tremors, headache, dizziness, and gastric irritation. Persons self-administering the drug for weight loss or to improve athletic performance have experienced nausea, vomiting, diaphoresis, palpitations, tachycardia, and myocardial infarction. Use of the drug may be confirmed by detecting its presence in semen or urine.[7]

Society and culture

Clenbuterol is not an ingredient of any therapeutic drug approved by the US Food and Drug Administration[citation needed] and is now banned for IOC-tested athletes.[8] In the US, administration of clenbuterol to any animal that could be used as food for human consumption is banned by the FDA.[9][10]

Weight-loss

Although often used by bodybuilders during their "cutting" cycles,[11] the drug has been more recently known to the mainstream, particularly through publicized stories of use by celebrities such as Victoria Beckham,[8] Britney Spears, and Lindsay Lohan, [12] for its off-label use as a weight-loss drug similar to usage of other sympathomimetic amines such as ephedrine, despite the lack of sufficient clinical testing either supporting or negating such use.

Performance-enhancing drug

As a β2 sympathomimetic, clenbuterol has also been used as a performance-enhancing drug.

A three-year suspension for taking clenbuterol kept sprinter Katrin Krabbe from competing in the 1992 Summer Olympics, and effectively ended her athletic career.[13][14]

In 2006, San Francisco Giants pitcher Guillermo Mota, while a member of the New York Mets, received a 50-game suspension after testing positive for clenbuterol.[15] In 2012, MLB officials announced they were again suspending Mota for 100 games due a positive test for clenbuterol.[16]

American swimmer Jessica Hardy tested positive at the US trials in 2008. She was subject to a one-year suspension, having claimed she unknowingly took the drug in a contaminated food supplement. Former New York Mets clubhouse employee Kirk Radomski admitted in his plea deal to distributing clenbuterol to dozens of current and former Major League Baseball players and associates.[17] After finishing fourth in the K-2 1000-m event at the 2008 Summer Olympics in Beijing, Polish sprint canoer Adam Seroczyński was disqualified for taking this drug, and Chinese cyclist Li Fuyu tested positive for it at the Dwars door Vlaanderen race in Belgium on March 24, 2010.[18]

In 2010, St. Louis Cardinals minor-league shortstop Lainer Bueno received a 50-game suspension for the 2011 season as a result of testing positive for clenbuterol.[19]

Cyclist Alberto Contador of Spain was banned for two years from professional cycling after testing positive for the drug at the 2010 Tour de France.[20] He was later stripped of the 2010 title of the Tour de France and the 2011 title of the Giro d'Italia.[21] CAS found that Contador probably tested positive due to a contaminated food supplement.[22] In 2013, Contador's teammate on the Team Saxo Bank squad, Michael Rogers, tested positive for clenbuterol at the Japan Cup bike race. In April 2014, the Union Cycliste Internationale announced that it accepted Rogers' explanation that the substance had been ingested by him after consuming contaminated meat whilst competing at the 2013 Tour of Beijing, upholding Rogers' disqualification from the Japan Cup, but declining to impose any further sanctions on him.[23]

In 2011, players of the Mexico national football team were found with clenbuterol in their bloodstreams, but were acquitted by WADA after they claimed the clenbuterol came from contaminated food. FIFA has also claimed 109 players from multiple countries who were participating in the Under-17 World Cup in Mexico tested positive for this drug. However, FIFA and the World Anti-Doping Agency declined to prosecute any cases because the weight of evidence pointed to contamination from Mexican meat.[24][25]

In 2013, Mexican boxer Erik Morales was suspended for two years after testing positive for clenbuterol.[26]

In 2014, Toronto Maple Leafs Forward Carter Ashton was suspended from the NHL for 20 games without pay for violating the NHL/NHL Players' Association Performance Enhancing Substances Program after it was determined that he had ingested clenbuterol. Carter claimed he used an unprescribed asthma inhaler.[27]

In 2014, South Korean swimmer Kim Ji-heun has tested positive for clenbuterol at an out-of-competition test on May 13, 2014. After completion of proceedings by the Korea Anti-Doping Disciplinary Panel, Kim received a two-year suspension, back-dated to the day of his positive test.[28]

In 2014, Czech body builder Petr Soukup received a lifetime ban after a positive test for clenbuterol along with methenolone, mesterolone, methamphetamine, oxandrolone, stanozolol, nandrolone, fluoxymesterone, CDMT ("Oral Turinabol"), and metandienone.[29]

In 2015, Yankees minor-league pitching prospect Moises Cedeno tested positive for clenbuterol and was suspended for 72 games.[30]

In 2015, two players from the Collingwood Football Club in Australia were delisted from the club and accepted two-year bans from all sport in Australia after testing positive to the substance, which they believe may have been in a contaminated illicit drug they consumed.[31][32]

In 2016, Australian heavyweight boxing champion Lucas Browne tested positive for clenbuterol.[33][34]

In 2016, Raul A. Mondesi tested positive for clenbuterol and was suspended 50 games from the Northwest Arkansas Naturals. MLB and the MLBPA agreed to reduce the suspension from 80 games to 50 games after Mondesi claimed it was found in cold medicine.[35]

In 2016, the California State Athletic Commission decided to issue Francisco Vargas a temporary boxing license on a probationary basis after he tested positive for clenbuterol.[36]

In 2018, British Olympic sprinter Nigel Levine was provisionally suspended for failing a drug test.[37]

In March 2018, champion boxer Canelo Alvarez tested positive for clenbuterol on two consecutive urine tests in February 2018.[38] This violation led to the cancellation of a heavily anticipated rematch between Alvarez and Gennady Golovkin, which was to be held on May 5, 2018. Alvarez blamed the positive tests on consumption of contaminated meats from Mexico. Notably, some Mexican beef farmers are known to add clenbuterol to cattle feed.[39]

Food contamination

Clenbuterol is occasionally referred to as "bute" and this risks confusion with phenylbutazone, also called "bute". Phenylbutazone, which is a drug also used with horses, was tested for in the 2013 European meat adulteration scandal.[40]

Intended to result in leaner meat with a higher muscle-to-fat ratio, the use of clenbuterol has been banned in meat since 1991 in the US and since 1996 in the European Union. The drug is banned due to health concerns about symptoms noted in consumers. These include increased heart rate, muscular tremors, headaches, nausea, fever, and chills. In several cases in Europe, these adverse symptoms have been temporary.[41]

Clenbuterol is a growth-promoting drug in the β agonist class of compounds. It is not licensed for use in China,[42] the United States,[41] or the EU[43] for food-producing animals, but some countries have approved it for animals not used for food, and a few countries have approved it for therapeutic uses in food-producing animals.

Not just athletes are affected by contamination. In Portugal, 50 people were reported as affected by clenbuterol in liver and pork between 1998 and 2002, while in 1990, veal liver was suspected of causing clenbuterol poisoning in 22 people in France and 135 people in Spain.[44]

In September 2006, some 330 people in Shanghai suffered from food poisoning after eating clenbuterol-contaminated pork.[45]

In February 2009, at least 70 people in one Chinese province (Guangdong) suffered food poisoning after eating pig organs believed to contain clenbuterol residue. The victims complained of stomachaches and diarrhea after eating pig organs bought in local markets.[46][47]

In March 2011, China's Ministry of Agriculture said the government would launch a one-year crackdown on illegal additives in pig feed, after a subsidiary of Shuanghui Group, China's largest meat producer, was exposed for using clenbuterol-contaminated pork in its meat products. A total of 72 people in central Henan Province, where Shuanghui is based, were taken into police custody for allegedly producing, selling, or using clenbuterol.[48] The situation has dramatically improved in China since September 2011, when a ban of clenbuterol was announced by China's Ministry of Agriculture.[49]

Authorities around the world appear to be issuing stricter food safety requirements, such as the Food Safety Modernization Act in the United States, Canada's revision of their import regulations, China's new food laws published since 2009, South Africa's new food law, and many more global changes and restrictions.

Veterinary use

The US and the EU prohibit the use of clenbuterol in food-producing animals.[50] It is, however, for the treatment of allergic respiratory disease in horses, as it is a bronchodilator. It can be used both orally and intravenously. It is also used in cattle to relax the uterus in cows, usually at the time of parturition.[51]

See also

  • Mabuterol (same structure as clenbuterol but one of the chloro groups has been changed to a trifluoromethyl group instead).
  • Cimaterol

References

  1. ^ Medicine, Center for Veterinary. "FOIA Drug Summaries - NADA 140-973 VENTIPULMIN® SYRUP - original approval". www.fda.gov. Retrieved 2016-03-10.
  2. ^ "874. Clenbuterol (WHO Food Additives Series 38)". www.inchem.org. Retrieved 2016-03-10.
  3. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 543. ISBN 9783527607495.
  4. ^ Pluim, BM; de Hon, O; Staal, JB; Limpens, J; Kuipers, H; Overbeek, SE; Zwinderman, AH; Scholten, RJ (1 January 2011). "β₂-Agonists and physical performance: a systematic review and meta-analysis of randomized controlled trials". Sports medicine (Auckland, N.Z.). 41 (1): 39–57. doi:10.2165/11537540-000000000-00000. PMID 21142283.
  5. ^ Dowling, Patricia M. "Systemic Therapy of Inflammatory Airway Disease". Merck Veterinary Manual. Retrieved 14 November 2018.
  6. ^ "Clenbuterol - SteroidAbuse .com". www.steroidabuse.com. Retrieved 2016-03-10.
  7. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 325–326.
  8. ^ a b Guest, Katy (2007-04-10). "Clenbuterol: The new weight-loss wonder drug gripping Planet Zero". The Independent. London. Archived from the original on 2007-04-08. Retrieved 2007-04-10. {{cite news}}: Unknown parameter |dead-url= ignored (|url-status= suggested) (help)
  9. ^ FDA's Prohibited Drug List, Food Animal Residue Avoidance & Depletion Program
  10. ^ "Animal Drugs @ FDA". www.accessdata.fda.gov. Retrieved 2016-03-10.
  11. ^ "Steroids and SARMS Handbook". Retrieved 2019-06-16.
  12. ^ "Clenbuterol Weight Loss Hollywood Secret". PRBuzz. London. 2012-05-17. Retrieved 2012-04-10.
  13. ^ "Philip Hersh - Series on Athletics in the GDR". www.runnersweb.com.
  14. ^ "Krabbe receives IAAF settlement". BBC News. 2002-04-30.
  15. ^ "Giants reliever Mota gets 100-game suspension". ESPN.com. 7 May 2012.
  16. ^ Dittmeier, Bobbie (May 7, 2012). "Mota suspended 100 games for positive test". MLB.com. Major League Baseball. Retrieved May 7, 2012.
  17. ^ Snyder, Whitney (2010-09-30). "Alberto Contador Tests Positive For Banned Substance". Huffington Post.
  18. ^ "Radioshack suspends Li after doping positive - Cyclingnews.com". cyclingnews.com.
  19. ^ "Three Minor League players suspended". MLB.com. September 30, 2010.
  20. ^ Macur, Juliet (29 September 2010). "With Positive Test, Contador May Lose Tour Title". The New York Times. Retrieved 29 September 2010.
  21. ^ CAS Sanction Contador with two year ban in clenbuterol case, cyclingnews.com, 6 February 2012
  22. ^ "Archived copy" (PDF). Archived from the original (PDF) on 2012-02-26. Retrieved 2011-02-13. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)CS1 maint: archived copy as title (link)
  23. ^ "Michael Rogers cleared to race as UCI accepts contaminated meat claim". theguardian.com. 23 April 2014. Retrieved 24 April 2014.
  24. ^ "FIFA alarmed by use of food supplements". September 5, 2012.
  25. ^ "Clenbuterol found in most players at Under-17 World Cup - ESPN". go.com.
  26. ^ "Boxer Erik Morales banned for two years for failed drug test". 22 March 2013 – via www.bbc.co.uk.
  27. ^ "Leafs' Ashton suspended 20 games for violating PED policy - TSN.ca". tsn.ca. 6 November 2014.
  28. ^ "[수영]이기흥 회장 "박태환, 리우올림픽 출전 의지 있다"" [Swimming: "Park Tae-hwan might miss the Olympic Games", according to the chairman] (in Korean). The Chosun Ilbo. 25 March 2015. Retrieved 22 April 2016.
  29. ^ "Antidopingový výbor ČR". www.antidoping.cz.
  30. ^ http://bigstory.ap.org/article/1c81c75a99cc4bbea4d97cbc90d9e6df/yankees-minor-league-pitcher-cedeno-suspended-72-games
  31. ^ "Magpies Keeffe, Thomas accept two-year doping bans". abc.net.au. 10 August 2015.
  32. ^ "No Cookies - Herald Sun". heraldsun.com.au.
  33. ^ "Heavyweight champ 'Big Daddy' Browne seeking legal advice over banned substance reports". ABC News. Retrieved 2016-03-22.
  34. ^ "Australia's first world heavyweight champion boxer Lucas Browne fails drug test". The Sydney Morning Herald. Retrieved 2016-03-22.
  35. ^ "Raul Mondesi Jr. suspended 50 games for PEDs found in cold medicine". CBS News. May 10, 2016.
  36. ^ "The Ring - The Bible of Boxing - News, Videos, Events and Ratings". The Ring.
  37. ^ "Nigel Levine: British sprinter provisionally suspended for failing drugs test". BBC Sport. 2018-02-07. Retrieved 2018-02-07.
  38. ^ "Canelo Alverez Tests Positive for Banned Substance, Blames Mexican Cows". TMZ. Retrieved 2018-03-05.
  39. ^ "Canelo Alvarez-Gennady Golovkin bout canceled following doping allegations". Washington Post. Retrieved 2018-04-04.
  40. ^ "Horse meat investigation. Advice for consumers". Enforcement and regulation. Food Standards Agency. Retrieved 19 May 2013.
  41. ^ a b "Clenbuterol" Archived 2012-08-29 at the Wayback Machine, Food Safety and Inspection Service (FSIS), July 1995, Retrieved 8 April 2015
  42. ^ China bans production, sale of clenbuterol to improve food safety Retrieved 08/22/2012
  43. ^ European Commission Archived 2012-08-10 at the Wayback Machine Retrieved 08/22/2012
  44. ^ Anti Doping Advisory Notes Retrieved 08/22/2012
  45. ^ Research Brief: Food Safety in China (PDF). China Environmental Health Project, Woodrow Wilson International Center for Scholars. June 28, 2007.
  46. ^ "China: 70 ill from tainted pig organs". CNN. 2009-02-23. Retrieved 2010-04-30.
  47. ^ Wang Ying (2009-02-23). "70 ill after eating tainted pig organs". China Daily.
  48. ^ "China to launch one-year crackdown on contaminated pig feed – xinhuanet.com". Xinhua. 2011-03-28. Retrieved 2011-03-29.
  49. ^ Bottemiller, helena (April 26, 2011). "Amid Scandal, China Bans More Food Additives". Food Safety News. Retrieved August 22, 2012.
  50. ^ "Import Alert 68-03". www.accessdata.fda.gov. Retrieved 2016-03-10.
  51. ^ Planipart Solution for Injection 30 micrograms/ml: Uses Archived 2011-07-21 at the Wayback Machine, National Office of Animal Health


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