From Wikipedia, the free encyclopedia Stanozolol
Stanozolol
Stanozolol 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(2
h12,14-17,24H,4-11H2,1-3H3,(H,22,23)/t14-,15+,16-,17-,19-,20-,21-/m0/s1
Key:LKAJKIOFIWVMDJ-IYRCEVNGSA-N Y
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Stanozolol,
Stanozolol commonly sold under the name Winstrol
(oral), Tenabol and Winstrol Depot (intramuscular), is a
synthetic anabolic steroid derived from testosterone. It
Systematic (IUPAC) name
(IUPAC) was developed by Winthrop Laboratories (Sterling Drug)
in 1962, and has been approved by the FDA for human
(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- use.
hexadecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-ol Unlike most injectable anabolic steroids, stanozolol is
not esterified and is sold as an aqueous suspension, or in
Clinical data
oral tablet form. The drug has a high oral bioavailabili-
AHFS/Drugs.com
AHFS/ Multum Consumer Information ty, due to a C17 α-alkylation which allows the hormone
to survive first-pass liver metabolism when ingested. It is
Pregnancy cat. X
because of this that stanozolol is also sold in tablet form.
Legal status Prescription only Stanozolol is usually considered a safer choice for fe-
(US) male bodybuilders in that its anabolic effects predomi-
Routes Oral, Intramuscular nate over its androgenic effects, although virilization and
masculinization are still very common even at low doses.
Pharmacokinetic data
Stanozolol has been used in both animal and human
Bioavailability ? patients for a number of conditions. In humans, it has
been demonstrated to be successful in treating anaemia
Metabolism Hepatic
and hereditary angioedema. Veterinarians may prescribe
Half-life 1 day the drug to improve muscle growth, red blood cell pro-
Excretion Renal: 84% duction, increase bone density and stimulate the appetite
of debilitated or weakened animals.
Identifiers Stanozolol is one of the anabolic steroids commonly
CAS number 10418-03-8 N used as a performance enhancing drug and is banned
from use in sports competition under the auspices of the
ATC code A14AA02 International Association of Athletics Federations (IAAF)
PubChem CID 25249 and many other sporting bodies. Additionally, stanozolol
has also been used in US horse racing.[1]
DrugBank DB06718
ChemSpider 23582 Y
Use in bodybuilding
UNII 4R1VB9P8V3 Y
In bodybuilding, stanozolol is typically "stacked"
KEGG D00444 Y with other testosterone-based anabolic steroids.
Stanozolol is preferred by many steroid users because it
ChEMBL CHEMBL1200324 N
causes strength increases without excess weight gain,[2]
Chemical data promotes increases in vascularity,[citation needed] and will
Formula C21H32N2O not convert to estrogen. It also does not cause excess wa-
ter retention, and is thought to have a diuretic effect on
Mol. mass 328.49 the body.[citation needed]
SMILES eMolecules & PubChem Stanozolol is commonly used by athletes and body-
builders alike to lose fat while retaining lean body mass.
1
From Wikipedia, the free encyclopedia Stanozolol
Law
In the United States, like other anabolic steroids,
stanozolol is classified as a controlled substance under
federal regulation. In New York, the state legislature clas-
sifies anabolic steroids under DEA Schedule III.
Publicized abuse cases
• 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.[6]
• 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.[7]
• Vita Pavlysh was stripped of her gold medal in shot
Seized stanozolol tablets. put at the 1999 IAAF World Indoor Championships
after she had tested positive for Stanozolol. 5 years
It is usually used in a "cutting cycle", to help preserve later at the 2004 IAAF World Indoor Championships
lean body mass while metabolizing adipose, although it in Budapest, Hungary, she won the title again only to
has not been proven conclusively that it has any special fail the drug test for the same reason. She was again
fat-burning properties. stripped of her title and banned from athletics for
It is presented most commonly as a 50 mg/mL injec- life.[8]
tion or a 5 mg tablet. However, recently 100 mg/mL ver- • Liudmyla Blonska, a Ukrainian heptathlete, tested
sions have become available. A common dosage can be positive for traces of Stanozolol shortly after
10–25 mg/day orally and 25–50 mg daily injected, with finishing thirteenth at the 2002 European
optimal results usually seen at 50 mg/day. It is reduced to Championships in Athletics and in June 2003 was
micrometer particles in aqueous suspension and does not handed a two year ban, whereafter she returned to
have a typical elimination half-life. Authentic stanozolol the sport.[9] At the 2008 Beijing Games, she was
can easily be seen, because it will separate in its con- stripped of a silver medal and given a lifetime ban
tainer if left undisturbed for a number of hours (the mi- after testing positive for stanozolol again.[10]
cronized crystal will fall to the bottom, and the water • Rafael Palmeiro was suspended 10 days from Major
suspension will rise to the top). It has a white, milky col- League Baseball on August 1, 2005, after testing
or. positive for steroids.[11] According to the published
An alternative to stanozolol is furazabol. Furazabol’s report in The New York Times, Stanozolol was the
effects are virtually identical to stanozolol except that in- steroid detected in Palmeiro’s system. This came not
stead of having an extremely adverse effect on choles- long after he testified before the United States House
terol values, furazabol actually improves a person’s blood Committee on Oversight and Government Reform on
lipid profile (at therapeutic doses, not performance en- steroid usage in baseball, and he denied ever using
hancing ones).[citation needed] Sold under the trade name steroids.
Miotolan, Furazabol is a standard treatment in Japan for • Barry Bonds is accused of using Stanozolol in Game of
hyperlipemia. Shadows, a book by Mark Fainaru-Wada and Lance
Williams. The accusations were first aired on 7
Detection of use March 2006 by Sports Illustrated, which published
Stanozolol is subject to extensive hepatic biotransforma- excerpts from the book.[12]
tion by a variety of enzymatic pathways. The primary • Salvador Carmona, footballer, tested positive for
metabolites are unique to stanozolol and are detectable Stanozolol in 2005 and 2006. He was banned for life
in the urine for up to 10 days after a single 5-10 mg oral by the Court of Arbitration for Sport (CAS) due to
dose. Methods for detection in urine specimens usually repeated drug offences. Tribunal Arbitral du
involve gas chromatography-mass spectrometry or liq- Sport.[13]
uid chromatography-mass spectrometry.[3][4][5] • 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
2
From Wikipedia, the free encyclopedia Stanozolol
"ambassador" for Swedish anti-steroid organization [3] Mateus-Avois L, Mangin P, Saugy M. Use of ion trap
Ren Idrott ("Clean Sports") and sports commentator gas chromatography-multiple mass spectrometry
for Swedish TV4. He lost both assignments as a for the detection and confirmation of
consequence.[14] 3’hydroxystanozolol at trace levels in urine for
• Phil Baroni, former UFC and PRIDE Fighting doping control. J. Chromatogr. B 816: 193-201, 2005.
Championship fighter, tested positive for Stanozolol [4] Pozo OJ, Van Eenoo P, Deventer K et al. Detection
following his June 22, 2007 fight against Frank and structural investigation of metabolites of
Shamrock at Strikeforce: Judgment Day.[15] stanozolol in human urine by liquid
• K-1’s 2007 World Grand Prix in Las Vegas finalist Zabit chromatography tandem mass spectrometry.
Samedov tested positive for Stanozolol following the Steroids 74: 837-852, 2009.
August 11, 2007 event.[16] [5] R. Baselt, Disposition of Toxic Drugs and Chemicals in
• Roger Clemens was reported to have been injected Man, 8th edition, Biomedical Publications, Foster
with stanozolol (Winstrol) by major league strength City, CA, 2008, pp. 1442-1443.
coach Brian McNamee during the 1998 baseball [6] "The most corrupt race ever". Guardian Unlimited
season.[17] (London). August 1, 2004.
• 2008 Triple Crown hopeful Big Brown was reported http://observer.guardian.co.uk/osm/story/
to have been injected with Winstrol, which is legal in 0,,1270863,00.html. Retrieved May 24, 2010
some states in US horse racing, by trainer Richard E. [7] Ivanova Sets First Record in Helsinki The Moscow
Dutrow, Jr. [18] Times.com, 8-8-2005
• Chris Leben, mixed martial artist, tested positive for [8] WOMEN’S SHOT-PUT CHAMPION BARRED FOR LIFE
the substance after UFC 89 where he was defeated by The New York Times, June 2, 2004
Michael Bisping and was suspended for 9 months.[19] [9] Blonska Thrown Out of Long Jump BBC Sport,
• Kirill Sidelnikov, mixed martial artist, tested positive August 21, 2008
for the substance after Affliction: Day of Reckoning [10] Ukrainian Blonska Given Life Ban BBC Sport,
where he was defeated by Paul Buentello and was August 29, 2008
suspended for 1 year and fined $2,500.[20] [11] Jenkins, Lee (August 3, 2005). "Popular Steroid Is at
• Tim Sylvia, mixed martial artist, tested positive for the Center of Palmeiro’s Case". The New York Times.
the drug Stanozolol after a Nevada State Athletic http://www.nytimes.com/2005/08/03/sports/
Commission test. As a result, Sylvia was stripped of baseball/
his title, served a 6-month suspension, and was fined 03steroids.html?ei=5090&en=c52da2e558ba4e10&ex=1280721600&
$10,000. Sylvia has stated that he used the drug to Retrieved May 24, 2010.
shed excess body fat and lose weight. [21] [12] Bonds exposed: Shadows details superstar slugger’s
• Cristiane Santos tested positive for anabolic steroids steroid use, Sports Illustrated, March 7, 2006
and as a result of the banned substance, her fight [13] "CAS 2006/A/1149 WADA v/ FMF & José Salvador
against Hiroko Yamanaka result has been changed to Carmona Alvarez", May 16, 2007 Accessed May 17,
a "No Contest" while Santos has had her license 2007
suspended and was fined $2500. Additionally, UFC [14] Carson, Alan (June 30, 2009). "Ex-Celt ace Hedman
president Dana White stripped Santos of her faces Steroids rap". The Sun.
Strikeforce 145 lb. women’s championship belt. [22] http://www.thesun.co.uk/scotsol/homepage/
news/2507007/Magnus-Hedman-is-charged-with-
Chemistry the-use-of-a-banned-steroid.html. Retrieved
November 3, 2010.
The pyrazole ring in stanozolol can be prepared by the [15] Ken Pishna (2007-07-03). "Breaking News: Phil
condensation of a keto-aldehyde with hydrazine.[23] Baroni Tests Positive". MMAWeekly.com.
http://www.mmaweekly.com/absolutenm/
templates/
dailynews.asp?articleid=4262&zoneid=13. Retrieved
2007-07-03.
[16] "Two Positive at K-1 World GP Vegas". Nokaut.
August 17, 2007. http://www.nokaut.com/
References ?id=12&solo_news=997&lang=e&cur=eur. Retrieved
2007-08-17.
[1] Win, Place, and Dope Slate, May 1, 2009 [17] All-Star Roster Shows Up on Mitchell Report
[2] "Winstrol Depot Information". WinstrolDepot.net. washingtonpost.com, 12-13-2007
http://www.winstroldepot.net/. Retrieved 6 [18] Bossert, Jerry; Red, Christian (May 16, 2008). "Big
January 2012. Brown’s legal doping a concern". Daily News (New
3
From Wikipedia, the free encyclopedia Stanozolol
York). http://www.nydailynews.com/sports/ [21] Sylvia Comes Clean sherdog.com, 10-13-2003
more_sports/2008/05/15/ [22] http://lowkick.blitzcorner.com/Strikeforce/How-
Does-Cyborgs-Failed-Drug-Test-Change-the-
2008-05-15_big_browns_legal_doping_a_concern.html?print=1&page=all.
[19] http://mma-live.com/chris-leben-fails- Landscape-of-WMMA-14823
ufc-89-drug-test/ [23] Clinton, R. O.; Manson, A. J.; Stonner, F. W.; Beyler,
[20] Sidelnikov Suspended for Steroid Use sherdog.com, A. L.; Potts, G. O.; Arnold, A. (1959). J. Amer. Chem.
03-03-2009 Soc. 81 (6): 1513. doi:10.1021/ja01515a060.
Retrieved from "http://en.wikipedia.org/w/index.php?title=Stanozolol&oldid=470645422"
Categories:
• Anabolic steroids
• Pyrazoles
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