|Synonyms||NSC-43193; WIN-14833; 17α-Methyl-2'H-androst-2-eno[3,2-c]pyrazol-17β-ol|
|AHFS/Drugs.com||Multum Consumer Information|
|By mouth, intramuscular injection|
|Drug class||Androgen; Anabolic steroid|
|Biological half-life||~24 hours|
|Chemical and physical data|
|Molar mass||328.49 g/mol|
|3D model (JSmol)|
|(what is this?)|
Stanozolol, sold under many brand names, is a synthetic anabolic–androgenic steroid (AAS) which was derived from dihydrotestosterone (DHT). It was developed by American pharmaceutical company Winthrop Laboratories (Sterling Drug) in 1962, and has been approved by the FDA for human use, though it is no longer marketed in this country.
Unlike most injectable AAS, 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 C17α 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 one of the AAS commonly used as performance-enhancing drugs 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.
Stanozolol has been used in both animals and human patients for a number of conditions. In humans, it has been demonstrated to be successful in treating anaemia and hereditary angioedema, the latter of which it has been specifically approved for the treatment of in some countries. 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 subject to non-medically supervised off-label use by some athletes for its anabolic properties frequently presenting with concomitant reduction of body fat. Stanozolol is a modified derivative of DHT and thus not aromatized to oestrogens via the aromatase class of enzymes (see chemical structure to right). Bodybuilders frequently misuse the term "dry" in describing their joint pain while using stanozolol either orally or via IM injection of an aqueous suspension; a reference to their perceived reason for an increase in joint pain. Rather, stanozolol as a DHT derivative can selectively compete with progesterone and other natural and synthetic progestins (nandrolone) for progestin receptors; yielding a reduction in progesterone mediated anti-inflammatory processes and presenting patients with a perception of increased joint discomfort.
Stanozolol is used by athletes and bodybuilders to lose fat while retaining lean body mass. It is usually used in a "cutting or leaning out" 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.
As an AAS, stanozolol is an agonist of the androgen receptor (AR), similarly to androgens like testosterone and DHT. It is not a substrate for 5α-reductase as it is already 5α-reduced, and so is not potentiated in so-called "androgenic" tissues like the skin, hair follicles, and prostate gland. This results in a greater ratio of anabolic to androgenic activity compared to testosterone. In addition, due to its 5α-reduced nature, stanozolol is non-aromatizable, and hence has no propensity for producing estrogenic effects such as gynecomastia or fluid retention. Stanozolol also does not possess any progestogenic activity of significance. Because of the presence of its 17α-methyl group, the metabolism of stanozolol is sterically hindered, resulting in it being orally active, although also hepatotoxic.
Stanozolol, also known as 17α-methyl-2'H-androst-2-eno[3,2-c]pyrazol-17β-ol, is a synthetic 17α-alkylated androstane steroid and a derivative of 5α-dihydrotestosterone (DHT) with a methyl group at the C17α position and a pyrazole ring attached to the A ring of the steroid nucleus.
Detection in body fluids
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.
Also in 1962, the Kefauver Harris Amendment was passed, amending the Federal Food, Drug, and Cosmetic Act to require drug manufacturers to provide proof of the effectiveness of their drugs before approval. The FDA implemented its Drug Efficacy Study Implementation (DESI) program to study and regulate drugs, including stanozolol, that had been introduced prior to the amendment. The DESI program was intended to classify all pre-1962 drugs that were already on the market as effective, ineffective, or needing further study. The FDA enlisted the National Research Council of the National Academy of Sciences to evaluate publications on relevant drugs under the DESI program.
In June 1970 the FDA announced its conclusions on the effectiveness of certain AAS, including stanozolol, based on the NAS/NRC reports made under DESI. The drugs were classified as probably effective as adjunctive therapy in the treatment of senile and postmenopausal osteoporosis but only as an adjunct, and in pituitary dwarfism (with a specific caveat for dwarfism, "until growth hormone is more available"), and as lacking substantial evidence of effectiveness for several other indications. Specifically, the FDA found a lack of efficacy for stanozolol as "an adjunct to promote body tissue-building processes and to reverse tissue-depleting processes in such conditions as malignant diseases and chronic nonmalignant diseases; debility in elderly patients, and other emaciating diseases; gastrointestinal disorders resulting in alterations of normal metabolism; use during pre-operative and postoperative periods in undernourished patients and poor-risk surgical cases due to traumatism; use in infants, children, and adolescents who do not reach an adequate weight; supportive treatment to help restore or maintain a favorable metabolic balance, as in postsurgical, postinfectious, and convalescent patients; of value in pre- operative patients who have lost tissue from a disease process or who have associated symptoms, such as anorexia; retention and utilization of calcium; surgical applications; gastrointestinal disease, malnourished adults, and chronic illness; pediatric nutritional problems; prostatic carcinoma; and endocrine deficiencies." The FDA gave Sterling six months to stop marketing stanozolol for the indications for which there was no evidence for efficacy, and one year to submit further data for the two indications for which it found probable efficacy.
In August and September 1970, Sterling submitted more data; the data was not sufficient but the FDA allowed the drug to be continued to be marketed, since there was an unmet need for drugs for osteoporosis and pituitary dwarfism, but Sterling was required to submit more data.
In 1980 the FDA removed the dwarfism indication from the label for stanozolol since human growth hormone drugs had come on the market, and mandated that the label for stanozolol and other steroids say: "As adjunctive therapy in senile and postmenopausal osteoporosis. AAS are without value as primary therapy but may be of value as adjunctive therapy. Equal or greater consideration should be given to diet, calcium balance, physiotherapy, and good general health promoting measures." and gave Sterling a timeline to submit further data for other indications it wanted for the drug. Sterling submitted data to the FDA intended to support the effectiveness of Winstrol for postmenopausal osteoporosis and aplastic anemia in December, 1980 and August 1983 respectively. The FDA's Endocrinologic and Metabolic Drugs Advisory Committee considered the data submitted for osteoporosis in two meetings held 1981 and the data for aplastic anemia in 1983.
In April 1984, the FDA announced that the data was not sufficient, and withdrew the marketing authority for stanozolol for senile and postmenopausal osteoporosis and for raising hemoglobin levels in aplastic anemia.
Sanofi had stanzolol manufactured in the US by Searle, which stopped making the drug in October 2002. Even with no drug in production, Sanofi sold the stanozolol business to Ovation Pharmaceuticals in 2003, along with the two other drugs. At that time, the drug had not been discontinued and was considered a treatment for hereditary angioedema. In March 2009, Lundbeck purchased Ovation
In 2010, Lundbeck withdrew stanozolol from the market in the US; as of 2014 no other company is marketing stanozolol as a pharmaceutical drug in the US but it can be obtained via a compounding pharmacy.
Pfizer had marketed stanozolol as a veterinary drug; in 2013 Pfizer spun off its veterinary business to Zoetis and in 2014 Pfizer transferred the authorizations to market injectable and tablet forms of stanozolol as a veterinary drug to Zoetis.
It is used in veterinary medicine as an adjunct in the management of wasting diseases, to stimulate the formation of red blood cells, arouse appetite, and promote weight gain, but the evidence for these uses is weak. It is used as a performance-enhancing drug in race horses. Its side effects include weight gain, water retention, and difficulty eliminating nitrogen-based waste products and it is toxic to the liver, especially in cats. Because it may promote the growth of tumors, it is contraindicated in dogs with enlarged prostates.:730-371
Stanozolol and other AAS were commonly used to treat hereditary angioedema attacks, until several drugs were brought to market specifically for treatment of that disease, the first in 2009: Cinryze, Berinert, ecallantide (Kalbitor), icatibant (Firazyr) and Ruconest. Stanozolol is still used long-term to reduce the frequency of severity of attacks.
Society and culture
Stanozolol is the generic name of stanozolol in English, German, French, and Japanese and its INN, USAN, USP, BAN, DCF, and JAN, while stanozololum is its name in Latin, stanozololo is its name in Italian and its DCIT, and estanozolol is its name in Spanish. Androstanazole, stanazol, stanazolol, and estanazolol are unofficial synonyms of stanozolol. The drug is also known generically by its former developmental code names NSC-43193 and WIN-14833.
Brand names under which stanozolol is or has been marketed include Anaysynth, Menabol, Neurabol Caps., Stanabolic (veterinary), Stanazol (veterinary), Stanol, Stanozolol, Stanztab, Stargate (veterinary), Stromba, Strombaject, Sungate (veterinary), Tevabolin, Winstrol, Winstrol Depot, and Winstrol-V (veterinary).
The examples and perspective in this article deal primarily with the United States and do not represent a worldwide view of the subject. (January 2012) (Learn how and when to remove this template message)
In the United States, like other AAS, stanozolol is classified as a controlled substance under federal regulation; they were included as Schedule III controlled substances under the Anabolic Steroids Act, which was passed as part of the Crime Control Act of 1990.:30 In New York, the state legislature classifies AAS under DEA Schedule III.
Stanozolol and other synthetic steroids were first banned by the International Olympic Committee and the International Association of Athletics Federations in 1974, after methods to detect them had been developed.:716
Stanozol is especially widely used by the athletes from post-Soviet countries.
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.
- 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.
- Australian National Rugby League footballer Rodney Howe was banned for 22 matches in 1998 for using stanozolol.
- 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.
- 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. At the 2008 Beijing Games, she was stripped of a silver medal and given a lifetime ban after testing positive for stanozolol again.
- Rafael Palmeiro was suspended 10 days from Major League Baseball on August 1, 2005, after testing positive for steroids. 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.
- 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.
- 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.
- 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.
- K-1's 2007 World Grand Prix in Las Vegas finalist Zabit Samedov tested positive for stanozolol following the August 11, 2007 event.
- Roger Clemens was reported to have been injected with stanozolol (Winstrol) by major league strength coach Brian McNamee during the 1998 baseball season.
- 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. 
- 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.
- 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.
- 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.
- Cristiane Justino tested positive for AAS and as a result of the banned substance, her fight against Hiroko Yamanaka result has been changed to a "No Contest" while Cristiane has had her license suspended and was fined $2500.
- Hysen Pulaku, an Albanian weightlifter, was expelled from the 2012 Olympics after testing positive for stanozolol.
- Zane Botha, a South African rugby player, was banned from competing in rugby for 2 years in January 2013 after testing positive for stanozolol.
- David Rollins, Seattle Mariners pitcher, was suspended for 80 games in 2015 after testing positive for stanozolol.
- Ervin Santana, Minnesota Twins pitcher, was suspended for 80 games without pay in 2015 after testing positive for stanozolol.
- Jenrry Mejía, New York Mets pitcher, was suspended for 80 games without pay early in 2015 after testing positive for stanozolol, and another 162 later in the season after a second positive test.
- Sheila Ocasio, Puerto Rican volleyball player, tested positive before the bronze medal match lost 1-3 to by her national team to the Dominican Republic in the 2015 Pan American Games and could not play that game.
- Mauricio Fiol, Peruvian swimmer, tested positive for stanozolol after winning the silver medal in the 200-metre butterfly at the 2015 Pan American Games. He was stripped of his medal and disqualified from competing in the 2016 Olympics by FINA.
- Ilya Ilyin, Kaz weightlifter and world record holder tested positive for stanozolol in 2016 after a reanalysis of his B-sample test from the 2012 London Olympics.
- Pradeep Sangwan, Left-arm Medium pace bowler from Delhi tested positive for stanozolol in the 2013 IPL season while playing for the Kolkata Knight Riders franchise in the IPL. He was banned for 18 months.
- "Stanozolol - Drugs.com".
- Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 961–. ISBN 978-3-88763-075-1.
- William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 726–737. ISBN 978-0-9828280-1-4.
- "Drugs@FDA: FDA Approved Drug Products". www.accessdata.fda.gov. Retrieved 2016-02-18.
- Win, Place, and Dope Slate, May 1, 2009
- Brent C Mangus; Michael G Miller (11 January 2005). Pharmacology Application in Athletic Training. F.A. Davis. pp. 151–. ISBN 978-0-8036-2027-8.
- "Stanozolol (PIM 918)". www.inchem.org. Retrieved 2016-02-18.
- Kicman, A T (2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC . PMID 18500378.
- Mateus-Avois L, Mangin P, Saugy M (2005). "Use of ion trap gas chromatography-multiple mass spectrometry for the detection and confirmation of 3'hydroxystanozolol at trace levels in urine for doping control". Journal of Chromatography B. 816 (1-2): 193–201. doi:10.1016/j.jchromb.2004.11.033. PMID 15664350.
- Pozo OJ, Van Eenoo P, Deventer K, Lootens L, Grimalt S, Sancho JV, Hernández F, Meuleman P, Leroux-Roels G, Delbeke FT (2009). "Detection and structural investigation of metabolites of stanozolol in human urine by liquid chromatography tandem mass spectrometry". Steroids. 74 (10-11): 837–52. doi:10.1016/j.steroids.2009.05.004. PMID 19464304.
- Baselt, R. (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 1442–3.
- Levin J, Trafford JA, Bishop PM. Stanozolol, a new anabolic steroid. J New Drugs. 1962 Jan-Feb;2:50-5. PMID 14464563
- "Promoting Safe and Effective Drugs for 100 Years". The Kefauver-Harris Drug Amendments. U.S. Food and Drug Administration.
- Pharmacy Today. August 2008. FDA aims to remove unapproved drugs from market: Risk-based enforcement program focuses on removing potentially harmful products
- National Academies of Sciences archives. The Drug Efficacy Study of the National Research Council’s Division of Medical Sciences, 1966-1969
- Food and Drug Administration Notice. "DESI 7630. Certain Anabolic Steroids. Drugs for Human Use: Drug Efficacy Study Implementation" Federal Register Vol 35, No. 122. June 24, 1970. page 10327–28
- Food and Drug Administration Notice. Docket No 80N-0276; DESI 7630. Winstrol Tablets; Drugs for Human Use; Drug Efficacy Study Implementation, Revocation of Exemption; Followup Notice and Opportunity for Hearing on Proposal to Withdraw Approval of New Drug Federal Register, April 23, 1984. page 17094-99
- Food and Drug Administration Notice. Docket No 80N-0276; Drugs for Human Use; Drug Efficacy Study Implementation; Conditions for Continued Marketing of Anabolic Steroids for Treatment Federal Register Vol 45 No. 213. October 31 1980. pages 72291-93
- The Pink Sheet 30 April 1984 Sterling Winstrol (Stanozolol) NDA Withdrawal Process Beginning, FDA
- Joseph C. Collins And John R. Gwilt The Life Cycle of Sterling Drug, Inc. Bull. Hist. Chem., VOLUME 25, Number 1 (2000)
- "Kodak to Sell Drug Unit for $1.68 Billion". Los Angeles Times. June 24, 1994. Retrieved 3 May 2013.
- Ovation Pharmaceuticals Products Archive of website captured January 10, 2004]
- PRnewswire. 7 August 2003. Press release: Ovation Pharmaceuticals Acquires Mebaral(R), Chemet(R), and Winstrol(R) From Sanofi-Synthelabo Inc.
- Reuters. 19 March 2009 Press Release: GTCR Completes the Sale of Ovation Pharmaceuticals to Lundbeck
- Notice by the Food and Drug Administration in the US Federal Register. 21 July 2010 Novartis Pharmaceuticals Corp. et al.; Withdrawal of Approval of 27 New Drug Applications and 58 Abbreviated New Drug Applications
- FDA Drugs@FDA: Stanozolol
- The US Hereditary Angioedema Association Treatments
- Timothy J. Craig and Neelu Kalra for MedScape Education. Contemporary Issues in Prophylactic Therapy of Hereditary Angioedema Released: 10/04/2010; Reviewed and Renewed: 07/30/2012.
- Zoetis. 24 June 2013 Zoetis Press Release: Zoetis Becomes Fully Independent With Acceptance of Pfizer Shares Tendered in Exchange Offer
- A Rule by the Food and Drug Administration, published in the Federal Register 20 May 2014 Implantation or Injectable Dosage Form New Animal Drugs; Change of Sponsor
- A Rule by the Food and Drug Administration, published in the Federal Register 25 March 2014 Oral Dosage Form New Animal Drugs; Change of Sponsor
- Jim E. Riviere, Mark G. Papich. Veterinary Pharmacology and Therapeutics. John Wiley & Sons, 2013 ISBN 9781118685907
- Merck Manual. Hereditary and Acquired Angioedema Last full review/revision March 2014 by Peter J. Delves, PhD
- I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 261–. ISBN 978-94-011-4439-1.
- Steven B. Karch. Pathology, Toxicogenetics, and Criminalistics of Drug Abuse. CRC Press, 2007 ISBN 9781420054569
- Shänzer, W. Abuse of Androgens and Detection of Illiegal Use. Chapter 24 in Testosterone: Action, Deficiency, Substitution, edited by E. Nieschlag, H. M. Behr. Cambridge University Press, 2004. ISBN 9781139452212
- "The most corrupt race ever". Guardian Unlimited. London. August 1, 2004. Retrieved May 24, 2010.
- Ivanova Sets First Record in Helsinki The Moscow Times.com, 8-8-2005
- Hooper, James (5 October 2006). "Webcke defends 'cover-up'". Fox Sports. Retrieved 13 August 2012.
- WOMEN'S SHOT-PUT CHAMPION BARRED FOR LIFE The New York Times, June 2, 2004
- Blonska Thrown Out of Long Jump BBC Sport, August 21, 2008
- Ukrainian Blonska Given Life Ban BBC Sport, August 29, 2008
- Jenkins, Lee (August 3, 2005). "Popular Steroid Is at the Center of Palmeiro's Case". The New York Times. Retrieved May 24, 2010.
- Bonds exposed: Shadows details superstar slugger's steroid use, Sports Illustrated, March 7, 2006
- "CAS 2006/A/1149 WADA v/ FMF & José Salvador Carmona Alvarez" Archived 2007-08-07 at the Wayback Machine., May 16, 2007 Accessed May 17, 2007
- Carson, Alan (June 30, 2009). "Ex-Celt ace Hedman faces Steroids rap". The Sun. London. Retrieved November 3, 2010.
- Ken Pishna (2007-07-03). "Breaking News: Phil Baroni Tests Positive". MMAWeekly.com. Archived from the original on 2007-09-13. Retrieved 2007-07-03.
- "Two Positive at K-1 World GP Vegas". Nokaut. August 17, 2007. Retrieved 2007-08-17. External link in
- All-Star Roster Shows Up on Mitchell Report washingtonpost.com, 12-13-2007
- Bossert, Jerry; Red, Christian (May 16, 2008). "Big Brown's legal doping a concern". Daily News. New York.
- "Chris Leben fails UFC Drug Test – MMA-Live.com". mma-live.com.
- Sidelnikov Suspended for Steroid Use sherdog.com, 03-03-2009
- Sylvia Comes Clean sherdog.com, 10-13-2003
- "Pulaku fails drugs test". Sky Sports.
- "Tuks star banned for doping".
- "Mariners' David Rollins suspended for 80 games". 27 March 2015.
- "Mets pitcher Jenrry Mejia hit with 80-game ban for PEDs". Daily News. New York. April 11, 2015.
- Puma, Mike (July 28, 2015). "Mets' Jenrry Mejia banned 162 games after 2nd failed PED test". New York Post.
- Brown, Andy (2015-09-10). "PASO confirms six more Toronto 2015 positives". The Sports Integrity Initiative. Retrieved 2015-11-13.
- "Dominicanas ganan bronce en voleibol de Toronto-2015" [Dominicans won bronze in volleyball at Toronto 2015] (in Spanish). Prensa Latina. 2015-07-25. Retrieved 2015-07-26.
- Aguirregomezcorta, Gonzalo (2015-07-26). "Sheila Ocasio da positivo por dopaje" [Sheila Ocasio tested positive for doping] (in Spanish). ESPN Deportes. Retrieved 2015-11-13.
- "Peru swimmer barred from 2016 Olympics for doping". Peru Reports. Retrieved 15 March 2016.
- "PUBLIC DISCLOSURES | International Weightlifting Federation". Retrieved 2016-06-16.
- "BCCI Anti-Doping tribunal bans Pradeep Sangwan". The Hindu. Retrieved 19 October 2013.