Stanozolol

Systematic (IUPAC) name
(1S,3aS,3bR,5aS,10aS,10bS,12aS)-1,10a,12a-trimethyl-1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b,11,12,12a-hexadecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-ol
Clinical data
AHFS/Drugs.com	Multum Consumer Information
Pregnancy cat.	X
Legal status	Prescription only (US)
Routes	Oral, Intramuscular
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Half-life	1 day
Excretion	Renal: 84%
Identifiers
CAS number	10418-03-8 N
ATC code	A14AA02
PubChem	CID 25249
DrugBank	DB06718
ChemSpider	23582 Y
UNII	4R1VB9P8V3 Y
KEGG	D00444 Y
ChEMBL	CHEMBL1200324 N
Chemical data
Formula	C21H32N2O
Mol. mass	328.49
SMILES	eMolecules & PubChem
InChI InChI=1S/C21H32N2O/c1-19-11-13-12-22-23-18(13)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,24H,4-11H2,1-3H3,(H,22,23)/t14-,15+,16-,17-,19-,20-,21-/m0/s1 Y Key:LKAJKIOFIWVMDJ-IYRCEVNGSA-N Y
N (what is this?)  (verify)

Stanozolol, commonly sold under the name Winstrol (oral), Tenabol and Winstrol Depot (intramuscular), is a synthetic anabolic steroid derived from dihydrotestosterone. It was developed by Winthrop Laboratories (Sterling Drug) in 1962, and has been approved by the FDA for human use.

Unlike most injectable anabolic steroids, stanozolol is not esterified and is sold as an aqueous suspension, or in oral tablet form. The drug has a high oral bioavailability, due to a C17 α-alkylation which allows the hormone to survive first-pass liver metabolism when ingested. It is because of this that stanozolol is also sold in tablet form.

Stanozolol is usually considered a safer choice for female bodybuilders in that its anabolic effects predominate over its androgenic effects, although virilization and masculinization are still very common even at low doses.^{[citation needed]}

Stanozolol has been used in both animal and human patients for a number of conditions. In humans, it has been demonstrated to be successful in treating anaemia and hereditary angioedema. Veterinarians may prescribe the drug to improve muscle growth, red blood cell production, increase bone density and stimulate the appetite of debilitated or weakened animals.

Stanozolol is one of the anabolic steroids commonly used as a performance enhancing drug and is banned from use in sports competition under the auspices of the International Association of Athletics Federations (IAAF) and many other sporting bodies. Additionally, stanozolol has been used in US horse racing.^[1]

Use in bodybuilding[link]

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In bodybuilding, stanozolol is typically "stacked" with other testosterone-based anabolic steroids. Stanozolol is preferred by many steroid users because it causes strength increases without excess weight gain, promotes increases in vascularity,^{[citation needed]} and will not convert to estrogen. It also does not cause excess water retention, and is thought to have a diuretic effect on the body.^{[citation needed]}

Stanozolol is commonly used by athletes and bodybuilders alike to lose fat while retaining lean body mass. It is usually used in a "cutting cycle", to help preserve lean body mass while metabolizing adipose, although it has not been proven conclusively that it has any special fat-burning properties.

It is presented most commonly as a 50 mg/mL injection or a 5 mg tablet. However, recently 100 mg/mL versions have become available. A common dosage can be 10–25 mg/day orally and 25–50 mg daily injected, with optimal results usually seen at 50 mg/day. It is reduced to micrometer particles in aqueous suspension and does not have a typical elimination half-life. Authentic stanozolol can easily be seen, because it will separate in its container if left undisturbed for a number of hours (the micronized crystal will fall to the bottom, and the water suspension will rise to the top). It has a white, milky color.

An alternative to stanozolol is furazabol. Furazabol's effects are virtually identical to stanozolol except that instead of having an extremely adverse effect on cholesterol values, furazabol actually improves a person's blood lipid profile (at therapeutic doses, not performance enhancing ones).^{[citation needed]} Sold under the trade name Miotolan, Furazabol is a standard treatment in Japan for hyperlipemia.

Detection of use[link]

Stanozolol is subject to extensive hepatic biotransformation by a variety of enzymatic pathways. The primary metabolites are unique to stanozolol and are detectable in the urine for up to 10 days after a single 5-10 mg oral dose. Methods for detection in urine specimens usually involve gas chromatography-mass spectrometry or liquid chromatography-mass spectrometry.^[2][3][4]

Law[link]

The examples and perspective in this article deal primarily with the United States and do not represent a worldwide view of the subject. Please improve this article and discuss the issue on the talk page. (January 2012)

In the United States, like other anabolic steroids, stanozolol is classified as a controlled substance under federal regulation. In New York, the state legislature classifies anabolic steroids under DEA Schedule III.

Publicized abuse cases[link]

• Ben Johnson was stripped of his gold medal in the 100 meter sprint at the 1988 Summer Olympics when he tested positive for stanozolol after winning the final.^[5]
• Olimpiada Ivanova was stripped of her silver medal in the 10 kilometer walk at the 1997 World Championships in Athletics after she had tested positive for Stanozolol, and she was banned for two years.^[6]
• Vita Pavlysh was stripped of her gold medal in shot put at the 1999 IAAF World Indoor Championships after she had tested positive for Stanozolol. 5 years later at the 2004 IAAF World Indoor Championships in Budapest, Hungary, she won the title again only to fail the drug test for the same reason. She was again stripped of her title and banned from athletics for life.^[7]
• Liudmyla Blonska, a Ukrainian heptathlete, tested positive for traces of Stanozolol shortly after finishing thirteenth at the 2002 European Championships in Athletics and in June 2003 was handed a two year ban, whereafter she returned to the sport.^[8] At the 2008 Beijing Games, she was stripped of a silver medal and given a lifetime ban after testing positive for stanozolol again.^[9]
• Rafael Palmeiro was suspended 10 days from Major League Baseball on August 1, 2005, after testing positive for steroids.^[10] According to the published report in The New York Times, Stanozolol was the steroid detected in Palmeiro's system. This came not long after he testified before the United States House Committee on Oversight and Government Reform on steroid usage in baseball, and he denied ever using steroids.
• Barry Bonds is accused of using Stanozolol in Game of Shadows, a book by Mark Fainaru-Wada and Lance Williams. The accusations were first aired on 7 March 2006 by Sports Illustrated, which published excerpts from the book.^[11]
• Salvador Carmona, footballer, tested positive for Stanozolol in 2005 and 2006. He was banned for life by the Court of Arbitration for Sport (CAS) due to repeated drug offences. Tribunal Arbitral du Sport.^[12]
• Magnus Hedman, footballer, was charged and convicted by Swedish court in June 2009 when he tested positive for Stanozolol. At the time he was a "ambassador" for Swedish anti-steroid organization Ren Idrott ("Clean Sports") and sports commentator for Swedish TV4. He lost both assignments as a consequence.^[13]
• Phil Baroni, former UFC and PRIDE Fighting Championship fighter, tested positive for Stanozolol following his June 22, 2007 fight against Frank Shamrock at Strikeforce: Judgment Day.^[14]
• K-1's 2007 World Grand Prix in Las Vegas finalist Zabit Samedov tested positive for Stanozolol following the August 11, 2007 event.^[15]
• Roger Clemens was reported to have been injected with stanozolol (Winstrol) by major league strength coach Brian McNamee during the 1998 baseball season.^[16]
• 2008 Triple Crown hopeful Big Brown was reported to have been injected with Winstrol, which is legal in some states in US horse racing, by trainer Richard E. Dutrow, Jr. ^[17]
• Chris Leben, mixed martial artist, tested positive for the substance after UFC 89 where he was defeated by Michael Bisping and was suspended for 9 months.^[18]
• Kirill Sidelnikov, mixed martial artist, tested positive for the substance after Affliction: Day of Reckoning where he was defeated by Paul Buentello and was suspended for 1 year and fined $2,500.^[19]
• Tim Sylvia, mixed martial artist, tested positive for the drug Stanozolol after a Nevada State Athletic Commission test. As a result, Sylvia was stripped of his title, served a 6-month suspension, and was fined $10,000. Sylvia has stated that he used the drug to shed excess body fat and lose weight. ^[20]
• Cristiane Santos tested positive for anabolic steroids and as a result of the banned substance, her fight against Hiroko Yamanaka result has been changed to a "No Contest" while Santos has had her license suspended and was fined $2500. Additionally, UFC president Dana White stripped Santos of her Strikeforce 145 lb. women's championship belt. ^[21]

Chemistry[link]

The pyrazole ring in stanozolol can be prepared by the condensation of a keto-aldehyde with hydrazine.^[22]

References[link]