Metandienone, also known as methandienone or methandrostenolone and sold under the brand name Dianabol (D-Bol) among others, is an androgen and anabolic steroid (AAS) medication which is still quite often used because of its affordability and effectiveness for bulking cycles.[4][5][1][6] It is also used non-medically for physique- and performance-enhancing purposes.[1] It is often taken by mouth.[1]
Metandienone was originally developed in 1955 by CIBA and marketed in Germany and the United States.[1][7][4][8][9] As the CIBA product Dianabol, metandienone quickly became the first widely used AAS among professional and amateur athletes, and remains the most common orally active AAS for non-medical use.[10][8][11][12] It is currently a controlled substance in the United States[13] and United Kingdom[14] and remains popular among bodybuilders. Metandienone is readily available without a prescription in certain countries such as Mexico, and is also manufactured in some Asian countries.[6]
Notes: Men produce about 3 to 11 mg of testosterone per day (mean 7 mg/day in young men). Footnotes:a = Never marketed. b = No longer used and/or no longer marketed. Sources: See template.
Metandienone is subject to extensive hepatic biotransformation by a variety of enzymatic pathways. The primary urinary metabolites are detectable for up to 3 days, and a recently discovered hydroxymethyl metabolite is found in urine for up to 19 days after a single 5 mg oral dose.[27] Several of the metabolites are unique to metandienone. Methods for detection in urine specimens usually involve gas chromatography-mass spectrometry.[28][29]
History
Metandienone was first described in 1955.[1] It was synthesized by researchers at the CIBA laboratories in Basel, Switzerland. CIBA filed for a U.S. patent in 1957,[30] and began marketing the drug as Dianabol in 1958 in the U.S.[1][31] It was initially prescribed to burn victims and the elderly. It was also prescribed off-label as a pharmaceutical performance enhancement to weight lifters and other athletes.[32] Early adopters included players for Oklahoma University and San Diego Chargers head coach Sid Gillman, who administered Dianabol to his team starting in 1963.[33]
After the Kefauver Harris Amendment was passed in 1962, the U.S. FDA began the DESI review process to ensure the safety and efficacy of drugs approved under the more lenient pre-1962 standards, including Dianabol.[34] In 1965, the FDA pressured CIBA to further document its legitimate medical uses, and re-approved the drug for treating post-menopausal osteoporosis and pituitary-deficient dwarfism.[35] After CIBA's patent exclusivity period lapsed, other manufacturers began to market generic metandienone in the U.S.
Following further FDA pressure, CIBA withdrew Dianabol from the U.S. market in 1983.[1] Generic production shut down two years later, when the FDA revoked metandienone's approval entirely in 1985.[1][35][36] Non-medical use was outlawed in the U.S. under the Anabolic Steroids Control Act of 1990.[37] While metandienone is controlled and no longer medically available in the U.S., it continues to be produced and used medically in some other countries.[1]
Metandienone is the generic name of the drug and its INNTooltip International Nonproprietary Name, while methandienone is its BANTooltip British Approved Name and métandiénone is its DCFTooltip Dénomination Commune Française.[7][4][5][6] It is also referred to as methandrostenolone and as dehydromethyltestosterone.[7][4][5][1][6] The former synonym should not be confused with methylandrostenolone, which is another name for a different AAS known as metenolone.[4]
Brand names
Metandienone was introduced and formerly sold primarily under the brand name Dianabol.[7][4][5][6][1] It has also been marketed under a variety of other brand names including Anabol, Averbol, Chinlipan, Danabol, Dronabol, Metanabol, Methandon, Naposim, Reforvit-B, and Vetanabol among others.[7][4][5][6][1]
^Yesalis C, Bahrke M (2002). "History of Doping in Sport"(PDF). International Sports Studies. 24: 42–76. Archived from the original(PDF) on 2017-11-23. Retrieved 2017-01-14.
^National Drug Code Directory. Consumer Protection and Environmental Health Service, Public Health Service, U.S. Department of Health, Education, and Welfare. 1982. pp. 642–.
^Federal Register. Office of the Federal Register, National Archives and Records Service, General Services Administration. 18 January 1983. pp. 2208–2209.
^The National Formulary ... American Pharmaceutical Association. 1974. Tablets available — Methandrostenolone Tablets usually available contain the following amounts of methandrostenolone: 2.5 and 5 mg.
^Laron Z (April 1962). "Breast development induced by methandrostenolone (Dianabol)". The Journal of Clinical Endocrinology and Metabolism. 22 (4): 450–452. doi:10.1210/jcem-22-4-450. PMID14462467.
^Roselli CE (May 1998). "The effect of anabolic-androgenic steroids on aromatase activity and androgen receptor binding in the rat preoptic area". Brain Research. 792 (2): 271–6. doi:10.1016/S0006-8993(98)00148-6. PMID9593936. S2CID29441013.
^ abcdSchänzer W, Geyer H, Donike M (April 1991). "Metabolism of metandienone in man: identification and synthesis of conjugated excreted urinary metabolites, determination of excretion rates and gas chromatographic-mass spectrometric identification of bis-hydroxylated metabolites". The Journal of Steroid Biochemistry and Molecular Biology. 38 (4): 441–64. doi:10.1016/0960-0760(91)90332-y. PMID2031859. S2CID20197705.
^Saartok T, Dahlberg E, Gustafsson JA (June 1984). "Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin". Endocrinology. 114 (6): 2100–6. doi:10.1210/endo-114-6-2100. PMID6539197.
^Schänzer W, Geyer H, Fusshöller G, Halatcheva N, Kohler M, Parr MK, Guddat S, Thomas A, Thevis M (2006). "Mass spectrometric identification and characterization of a new long-term metabolite of metandienone in human urine". Rapid Communications in Mass Spectrometry. 20 (15): 2252–8. Bibcode:2006RCMS...20.2252S. doi:10.1002/rcm.2587. PMID16804957.
^Baselt R (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 952–4.
^Fragkaki AG, Angelis YS, Tsantili-Kakoulidou A, Koupparis M, Georgakopoulos C (May 2009). "Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine". The Journal of Steroid Biochemistry and Molecular Biology. 115 (1–2): 44–61. doi:10.1016/j.jsbmb.2009.02.016. PMID19429460. S2CID10051396.
^US granted 2900398, Wettstein A, Hunger A, Meystre C, Ehmann L, "Process for the manufacture of steroid dehydrogenation products", issued 18 August 1959, assigned to Ciba Pharmaceutical Products, Inc.
