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 |
ChEBI |
CHEBI:9249 N |
ChEMBL |
CHEMBL1200324 N |
Chemical data |
Formula |
C21H32N2O |
Mol. mass |
328.49 |
SMILES
- O[C@@]5(C)CC[C@H]4[C@H]3[C@@H]([C@]2(Cc1c(nnc1)C[C@@H]2CC3)C)CC[C@@]45C
|
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) 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 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]
Contents
- 1 Use in bodybuilding
- 2 Law
- 3 Publicized abuse cases
- 4 Chemistry
- 5 References
Use in bodybuilding
|
This section needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (January 2012) |
Seized stanozolol tablets.
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 dihydrotestosterone (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 as 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 peception of increased joint discomfort.
commonly used by athletes and bodybuilders alike to lose fat while retaining lean body mass.[citation needed] It is usually used in a "cutting or leaning out" cycle, to help preserve lean body mass while metabolizing adipose,[citation needed] although it has not been proven conclusively that it has any special fat-burning properties.[citation needed]
It is presented most commonly as a 50 mg/mL injection or a 5 mg tablet. However, recently 75mg/ml 100 mg/mL versions have become available
Detection of use
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
|
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 II.
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.[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]
- Australian National Rugby League footballer Rodney Howe was banned for 22 matches in 1998 for using stanozolol.[7]
- 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.[8]
- 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.[9] At the 2008 Beijing Games, she was stripped of a silver medal and given a lifetime ban after testing positive for stanozolol again.[10]
- Rafael Palmeiro was suspended 10 days from Major League Baseball on August 1, 2005, after testing positive for steroids.[11] 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.[12]
- 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.[13]
- 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.[14]
- 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.[15]
- K-1's 2007 World Grand Prix in Las Vegas finalist Zabit Samedov tested positive for stanozolol following the August 11, 2007 event.[16]
- Roger Clemens was reported to have been injected with stanozolol (Winstrol) by major league strength coach Brian McNamee during the 1998 baseball season.[17]
- 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. [18]
- 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.[19]
- 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.[20]
- 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.[21]
- 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.[22]
- Hysen Pulaku, an Albanian weightlifter, was expelled from the 2012 Olympics after testing positive for stanozolol.[23]
- Zane Botha, a South African rugby player, was banned from competing in rugby for 2 years in January 2013 after testing positive for stanozolol.[24]
Chemistry
The pyrazole ring in stanozolol can be prepared from oxymetholone by the condensation of a keto-aldehyde with hydrazine.[25]
References
- ^ Win, Place, and Dope Slate, May 1, 2009
- ^ Mateus-Avois L, Mangin P, Saugy M. 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. J. Chromatogr. B 816: 193-201, 2005.
- ^ Pozo OJ, Van Eenoo P, Deventer K et al. Detection and structural investigation of metabolites of stanozolol in human urine by liquid chromatography tandem mass spectrometry. Steroids 74: 837-852, 2009.
- ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1442-1443.
- ^ "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", 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. Retrieved 2007-07-03.
- ^ "Two Positive at K-1 World GP Vegas". Nokaut. August 17, 2007. Retrieved 2007-08-17.
- ^ 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).
- ^ http://mma-live.com/chris-leben-fails-ufc-89-drug-test/
- ^ Sidelnikov Suspended for Steroid Use sherdog.com, 03-03-2009
- ^ Sylvia Comes Clean sherdog.com, 10-13-2003
- ^ http://lowkick.blitzcorner.com/Strikeforce/How-Does-Cyborgs-Failed-Drug-Test-Change-the-Landscape-of-WMMA-14823
- ^ Sky Sports http://www1.skysports.com/olympics/story/21822/7945311 .
- ^ http://www.sport24.co.za/Rugby/VarsityCup/Tuks-star-banned-for-doping-20130306
- ^ Clinton, R. O.; Manson, A. J.; Stonner, F. W.; Beyler, A. L.; Potts, G. O.; Arnold, A. (1959). J. Amer. Chem. Soc. 81 (6): 1513. doi:10.1021/ja01515a060.
Anabolic steroids (A14)
|
|
Androstane (carbon 19 present) |
- Adrenosterone
- Androisoxazole
- Bolasterone (Myagen)
- Bolazine
- Boldione
- Boldenone undecylenate (Equipoise)
- 4-Chlordehydromethyltestosterone (Turinabol)
- 4-Hydroxytestosterone
- Calusterone
- Clostebol
- Danazol
- Desoxymethyltestosterone (Madol)
- DHT
- Drostanolone (Masteron)
- Enestebol
- Epitiostanol
- Fluoxymesterone (Halotestin)
- Formebolone
- Furazabol (Miotolan)
- Hydroxystenozole
- Mebolazine
- Mesabolone
- Mestanolone
- Mesterolone (Proviron)
- Methandriol
- Methandrostenolone (Dianabol)
- Metenolone
- Methenolone enanthate (Primobolan)
- Methasterone (Superdrol)
- Methyltestosterone
- Methyldiazirinol
- Oxandrolone (Anavar)
- Oxymetholone (Anadrol)
- Oxymesterone
- Prostanozol
- Quinbolone (Anabolicum Vister)
- Roxibolone
- Silandrone
- Stanozolol (Strombafort
- Winstrol)
- Stenbolone
- Testosterone`s (Sustamed
- Sustanon)
- 1-Testosterone
- Thiomesterone
|
|
Estrene (carbon 19 absent) |
- Bolenol
- Ethyldienolone
- Ethylestrenol
- Mibolerone (Cheque Drops)
- Methylnortestosterone
- Metribolone (R1881)
- Nandrolone (Deca Durabolin)
- Norboletone (Genabol)
- Norclostebol
- Norethandrolone
- Normethandrone
- Oxabolone cipionate
- Propetandrol
- Tetrahydrogestrinone (The Clear)
- Trenbolone (Fina)
- Trestolone
|
|
Prohormones |
- 1-Androstenediol
- 1,4-Androstadienedione
- 4-Androstenediol
- 4-Androstenedione
- 19-Norandrostenediol
- 19-Norandrostenedione
- DHEA
|
|
|
anat (t, g, p)/phys/devp/enzy
|
noco/cong/tumr, sysi/epon
|
proc, drug (A2A/2B/3/4/5/6/7/14/16), blte
|
|
|
|
Androgenics
|
|
Receptor |
|
|
Enzyme
(inhibitors) |
20,22-Desmolase
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
|
|
17α-Hydroxylase,
17,20-Lyase
|
- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone acetate
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Levonorgestrel
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
|
|
3β-HSD (I, II)
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Levonorgestrel
- Metyrapone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
|
|
17β-HSD (I-XIV)
|
|
|
5α-Reductase (I, II)
|
- 22-Oxime
- Alfatradiol
- Azelaic acid
- β-Sitosterol
- Bexlosteride
- Dutasteride
- Epitestosterone
- Epristeride
- Finasteride
- gamma-Linolenic acid
- Ganoderic acid
- Izonsteride
- L-39
- Lapisteride
- Polyunsaturated fatty acids (α-linolenic acid, linoleic acid, γ-linolenic acid, oleic acid)
- saw palmetto
- Turosteride
- Vitamin B6
- Zinc
|
|
Aromatase
|
- 1,4,6-Androstatriene-3,17-dione
- 4-Androstene-3,6,17-trione
- 4-Cyclohexylaniline
- 4-Hydroxytestosterone
- 5α-DHNET
- Abyssinone II
- Aminoglutethimide
- Anastrozole
- Ascorbic acid (Vitamin C)
- Atamestane
- Bifonazole
- CGP-45,688
- CGS-47,645
- Clotrimazole
- DHT
- Difeconazole
- Econazole
- Exemestane
- Fadrozole
- Fenarimol
- Finrozole
- Formestane
- Imazalil
- Isoconazole
- Ketoconazole
- Letrozole
- Liarozole
- MEN-11066
- Miconazole
- Minamestane
- Nimorazole
- NKS01
- ORG-33,201
- Penconazole
- Plomestane
- Prochloraz
- Propioconazole
- Pyridoglutethimide
- Rogletimide
- Rotenone
- Talarozole
- Testolactone
- Tioconazole
- Triadimefon
- Triadimenol
- Troglitazone
- Vorozole
- YM511
- Zinc
Note: 21-Hydroxylase inhibitors may also affect androgen levels as they prevent metabolism of androgen steroid precursors.
|
|
|
Other |
Endogenous
|
- Androgens: Dihydrotestosterone
- Testosterone
- Antiandrogens: Epitestosterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- Cortodoxone/Deoxycortisol
- DHEA
- DHEA sulfate
- Androstenediol
- Androstenedione
|
|
Indirect
|
- Estrogens/Antiestrogens (see here)
- GnRH agonists/antagonists (see here)
- Gonadotropins/Antigonadotropins (see here)
- Plasma proteins (SHBG, ABP, Albumin)
- Progestogens/Antiprogestins (see here)
- Prolactin
|
|
Procedures
|
- Adrenalectomy
- Hypophysectomy
- Oophorectomy
- Orchiectomy
|
|
|
Estrogenics
|
|
Receptor |
ER (α, β)
|
|
|
GPER
|
- Agonists: Estradiol
- Fulvestrant
- G-1
- Genistein
- Quercetin
- Tamoxifen
|
|
|
Enzyme
(inhibitors) |
20,22-Desmolase
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
|
|
17α-Hydroxylase,
17,20-Lyase
|
- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
|
|
3β-HSD
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Metyrapone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
|
|
17β-HSD
|
|
|
Aromatase
|
- 1,4,6-Androstatriene-3,17-dione
- 4-Androstene-3,6,17-trione
- 4-Cyclohexylaniline
- 4-Hydroxytestosterone
- 5α-DHNET
- Abyssinone II
- Aminoglutethimide
- Anastrozole
- Ascorbic acid (Vitamin C)
- Atamestane
- Bifonazole
- CGP-45,688
- CGS-47,645
- Clotrimazole
- DHT
- Difeconazole
- Econazole
- Exemestane
- Fadrozole
- Fenarimol
- Finrozole
- Formestane
- Imazalil
- Isoconazole
- Ketoconazole
- Letrozole
- Liarozole
- MEN-11066
- Miconazole
- Minamestane
- Nimorazole
- NKS01
- ORG-33,201
- Penconazole
- Plomestane
- Prochloraz
- Propioconazole
- Pyridoglutethimide
- Rogletimide
- Rotenone
- Talarozole
- Testolactone
- Tioconazole
- Triadimefon
- Triadimenol
- Troglitazone
- Vorozole
- YM511
- Zinc
Note: 5α-reductase and 21-hydroxylase inhibitors may also affect estrogen levels as they prevent metabolism of estrogen steroid precursors.
|
|
|
Other |
Endogenous
|
- Estrogens: 5α-Androstane-3β,17β-diol
- DHEA
- Estetrol
- Estradiol
- Estriol
- Estrone
- Antiestrogens: 2-Hydroxyestrone
- 16-Hydroxyestrone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- Cortodoxone/Deoxycortisol
- DHEA
- DHEA sulfate
- 16-Hydroxy-DHEA
- 16-Hydroxy-DHEA sulfate
- Androstenediol
- Androstenedione
- 16-Hydroxyandrostenedione
- Testosterone
|
|
Indirect
|
- Androgens/Antiandrogens (see here)
- Calcitriol (a form of Vitamin D)
- GnRH agonists/antagonists (see here)
- Gonadotropins//Antigonadotropins (see here)
- Plasma proteins (SHBG, ABP, Albumin)
- Progestogens/Antiprogestins (see here)
- Prolactin
|
|
Procedures
|
- Adrenalectomy
- Hypophysectomy
- Oophorectomy
- Orchiectomy
|
|
|
Progestogenics
|
|
Receptor |
|
|
Enzyme
(inhibitors) |
20,22-Desmolase
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
|
|
17α-Hydroxylase,
17,20-Lyase
|
- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone acetate
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Levonorgestrel
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
|
|
3β-HSD
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Metyrapone
- Norethisterone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
|
|
21-Hydroxylase
|
- Aminoglutethimide
- Amphenone B
- Bifonazole
- Clotrimazole
- Diazepam
- Econazole
- Genistein
- Isoconazole
- Ketoconazole
- Metyrapone
- Miconazole
- Midazolam
- Tioconazole
|
|
|
Other |
Endogenous
|
- Progestogens: Deoxycorticosterone
- 17-Hydroxyprogesterone
- Progesterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
|
|
Indirect
|
- Androgens/Antiandrogens (see here)
- Estrogens/Antiestrogens (see here)
- GnRH agonists/antagonists (see here)
- Gonadotropins/Antigonadotropins (see here)
- Plasma proteins (Transcortin, Albumin)
|
|
Procedures
|
- Adrenalectomy
- Hypophysectomy
- Oophorectomy
- Orchiectomy
|
|
|