Metandienone
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 mostly no longer prescribed.[6] Metandienone was formerly approved and marketed as a form of androgen replacement therapy for the treatment of hypogonadism in men, but has since been discontinued and withdrawn in most countries, including in the United States.[21][22] As with other 17α-alkylated steroids, methandienone poses a risk of hepatotoxicity and use over extended periods of time can result in liver damage without appropriate precautions.[medical citation needed] While it can be metabolized by 5α-reductase into methyl-1-testosterone (17α-methyl-δ1-DHT), a more potent AAS, the drug has extremely low affinity for this enzyme and methyl-1-testosterone is thus produced in only trace amounts.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.[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.[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.
Routes ofadministrationBy mouthintramuscular injectionveterinaryDrug classAndrogenAnabolic steroidATC codeA14AA03D11AE01Legal statusPharmacokineticBioavailabilityMetabolismHepaticElimination half-lifeExcretionCAS NumberChemSpiderChEMBLCompTox DashboardECHA InfoCardFormulaMolar massSMILESphysique- and performance-enhancing purposesSide effectssymptomsmasculinizationincreased hair growthsexual desireestrogenicfluid retentionbreast enlargementliver damageagonistandrogen receptorbiological targettestosteronedihydrotestosteroneanabolicandrogenicGermanyUnited Statescontrolled substanceUnited KingdombodybuildersprescriptionMexicoandrogen replacement therapyhypogonadismTestosterone undecanoateMethyltestosteroneFluoxymesteroneMesteroloneSublingualBuccalTransdermalAndrostanolone (DHT)RectalInjectionTestosterone propionateTestosterone enanthateTestosterone cypionateTestosterone isobutyrateTestosterone phenylacetateMixed testosterone estersTestosterone buciclateImplanttabletscompetitiveathletespowerliftersoily skinseborrheaincreased facial/body hair growthscalp hair lossvirilizationgynecomastiahepatotoxicityMethandriolDrostanoloneMetenoloneOxymetholoneOxandroloneStanozololNandroloneEthylestrenolNorethandroloneprotein synthesisglycogenolysismetabolized5α-reductasemethyl-1-testosteronepotentaffinityenzyme5α-reductase inhibitorsfinasteridedutasteridesubstratearomataseestrogenmethylestradiolmetabolism-resistantantiestrogenaromatase inhibitoranastrozoleselective estrogen receptor modulatortamoxifenprogestogenichepatotoxicsex hormone-binding globulinhydroxylationoxidation5β-reductionepimerizationconjugationreactionsdouble bond5α-reducedmetaboliteseliminatedList of androgens/anabolic steroidssyntheticandrostane