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| Clinical data | |
|---|---|
| Trade names | Dianabol, others |
| Other names | Methandienone; Methandrostenolone; Methandrolone; Dehydromethyltestosterone; Methylboldenone; Perabol; Ciba-17309-Ba; TMV-17; NSC-51180; NSC-42722; 17α-Methyl-δ1-testosterone; 17β-Hydroxy-17α-methylandrosta-1,4-dien-3-one; 17α-Methylandrost-1,4-dien-17β-ol-3-one |
| Routes of administration | By mouth,intramuscular injection (veterinary)[1] |
| Drug class | Androgen;Anabolic steroid |
| ATC code | |
| Legal status | |
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| Pharmacokinetic data | |
| Bioavailability | High |
| Metabolism | Hepatic |
| Eliminationhalf-life | 3–6 hours[1][3] |
| Excretion | Urine |
| Identifiers | |
| CAS Number |
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| PubChemCID | |
| DrugBank |
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| ChemSpider |
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| UNII | |
| KEGG | |
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.000.716 |
| Chemical and physical data | |
| Formula | C20H28O2 |
| Molar mass | 300.442 g·mol−1 |
| 3D model (JSmol) | |
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| S,9S,10S,13S,14S,17S)-17-Hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[aphenanthren-3-one&page2=Metandienone (verify)] | |
Metandienone, also known asmethandienone ormethandrostenolone and sold under the brand nameDianabol (D-Bol) among others, is anandrogen andanabolic steroid (AAS) medication which is mostly no longer prescribed.[4][5][1][6] It is also used non-medically forphysique- and performance-enhancing purposes.[1] It is often takenby mouth.[1]
Side effects of metandienone includesymptoms ofmasculinization likeacne,increased hair growth,voice changes, and increasedsexual desire,estrogenic effects likefluid retention andbreast enlargement, andliver damage.[1] The drug is anagonist of theandrogen receptor (AR), thebiological target of androgens liketestosterone anddihydrotestosterone (DHT), and has stronganabolic effects and moderateandrogenic effects.[1] It also has moderate estrogenic effects.[1]
Metandienone was originally developed in 1955 byCIBA and marketed inGermany and theUnited 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 acontrolled substance in the United States[13] andUnited Kingdom[14] and remains popular amongbodybuilders. Metandienone is readily available without aprescription in certain countries such asMexico, and is also manufactured in someAsian countries.[6]
Metandienone was formerly approved and marketed as a form ofandrogen replacement therapy for the treatment ofhypogonadism in men, but has since been discontinued and withdrawn in most countries, including in theUnited States.[15][4][6]
It was given at a dosage of 5 to 10 mg/day in men and 2.5 mg/day in women.[16][17][1]
| Route | Medication | Major brand names | Form | Dosage |
|---|---|---|---|---|
| Oral | Testosteronea | – | Tablet | 400–800 mg/day (in divided doses) |
| Testosterone undecanoate | Andriol, Jatenzo | Capsule | 40–80 mg/2–4× day (with meals) | |
| Methyltestosteroneb | Android, Metandren, Testred | Tablet | 10–50 mg/day | |
| Fluoxymesteroneb | Halotestin, Ora-Testryl, Ultandren | Tablet | 5–20 mg/day | |
| Metandienoneb | Dianabol | Tablet | 5–15 mg/day | |
| Mesteroloneb | Proviron | Tablet | 25–150 mg/day | |
| Sublingual | Testosteroneb | Testoral | Tablet | 5–10 mg 1–4×/day |
| Methyltestosteroneb | Metandren, Oreton Methyl | Tablet | 10–30 mg/day | |
| Buccal | Testosterone | Striant | Tablet | 30 mg 2×/day |
| Methyltestosteroneb | Metandren, Oreton Methyl | Tablet | 5–25 mg/day | |
| Transdermal | Testosterone | AndroGel, Testim, TestoGel | Gel | 25–125 mg/day |
| Androderm, AndroPatch, TestoPatch | Non-scrotal patch | 2.5–15 mg/day | ||
| Testoderm | Scrotal patch | 4–6 mg/day | ||
| Axiron | Axillary solution | 30–120 mg/day | ||
| Androstanolone (DHT) | Andractim | Gel | 100–250 mg/day | |
| Rectal | Testosterone | Rektandron, Testosteronb | Suppository | 40 mg 2–3×/day |
| Injection (IMTooltip intramuscular injection orSCTooltip subcutaneous injection) | Testosterone | Andronaq, Sterotate, Virosterone | Aqueous suspension | 10–50 mg 2–3×/week |
| Testosterone propionateb | Testoviron | Oil solution | 10–50 mg 2–3×/week | |
| Testosterone enanthate | Delatestryl | Oil solution | 50–250 mg 1x/1–4 weeks | |
| Xyosted | Auto-injector | 50–100 mg 1×/week | ||
| Testosterone cypionate | Depo-Testosterone | Oil solution | 50–250 mg 1x/1–4 weeks | |
| Testosterone isobutyrate | Agovirin Depot | Aqueous suspension | 50–100 mg 1x/1–2 weeks | |
| Testosterone phenylacetateb | Perandren, Androject | Oil solution | 50–200 mg 1×/3–5 weeks | |
| Mixed testosterone esters | Sustanon 100, Sustanon 250 | Oil solution | 50–250 mg 1×/2–4 weeks | |
| Testosterone undecanoate | Aveed, Nebido | Oil solution | 750–1,000 mg 1×/10–14 weeks | |
| Testosterone buciclatea | – | Aqueous suspension | 600–1,000 mg 1×/12–20 weeks | |
| Implant | Testosterone | Testopel | Pellet | 150–1,200 mg/3–6 months |
| 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 was provided in the form of 2.5, 5 and 10 mgoraltablets.[18][19][20][1]
Metandienone is used forphysique- and performance-enhancing purposes bycompetitiveathletes,bodybuilders, andpowerlifters.[1] It is said to be the most widely used AAS for such purposes both today and historically.[1]
Androgenicside effects such asoily skin,acne,seborrhea,increased facial/body hair growth,scalp hair loss, andvirilization may occur.[1]Estrogenic side effects such asgynecomastia andfluid retention can also occur.[1] Case reports of gynecomastia exist.[21][22] As with other 17α-alkylated steroids, methandienone poses a risk ofhepatotoxicity and use over extended periods of time can result inliver damage without appropriate precautions.[1]
| Medication | Ratioa |
|---|---|
| Testosterone | ~1:1 |
| Androstanolone (DHT) | ~1:1 |
| Methyltestosterone | ~1:1 |
| Methandriol | ~1:1 |
| Fluoxymesterone | 1:1–1:15 |
| Metandienone | 1:1–1:8 |
| Drostanolone | 1:3–1:4 |
| Metenolone | 1:2–1:3 |
| Oxymetholone | 1:2–1:9 |
| Oxandrolone | 1:13–1:3 |
| Stanozolol | 1:1–1:3 |
| Nandrolone | 1:3–1:16 |
| Ethylestrenol | 1:2–1:19 |
| Norethandrolone | 1:1–1:2 |
| Notes: In rodents.Footnotes:a = Ratio of androgenic to anabolic activity.Sources: See template. | |
Methandienone binds to and activates theandrogen receptor (AR) in order to exert its effects.[23] These include dramatic increases inprotein synthesis,glycogenolysis, and muscle strength over a short space of time.[medical citation needed] While it can bemetabolized by5α-reductase intomethyl-1-testosterone (17α-methyl-δ1-DHT), a morepotent AAS, the drug has extremely lowaffinity for thisenzyme and methyl-1-testosterone is thus produced in only trace amounts.[1][24] As such,5α-reductase inhibitors likefinasteride anddutasteride do not reduce the androgenic effects of metandienone.[1] Nonetheless, while the ratio ofanabolic toandrogenic activity of metandienone is improved relative to that oftestosterone, the drug does still possess moderate androgenic activity and is capable of producing severevirilization in women and children.[1] As such, it is only really commonly used in men.[1]
Metandienone is asubstrate foraromatase and can bemetabolized into theestrogenmethylestradiol (17α-methylestradiol).[1] While the rate of aromatization is reduced relative to that fortestosterone ormethyltestosterone, the estrogen produced ismetabolism-resistant and hence metandienone retains moderateestrogenic activity.[1] As such, it can cause side effects such asgynecomastia andfluid retention.[1] The co-administration of anantiestrogen such as anaromatase inhibitor likeanastrozole or aselective estrogen receptor modulator liketamoxifen can reduce or prevent such estrogenic side effects.[1] Metandienone has noprogestogenic activity.[1]
As with other 17α-alkylated AAS, metandienone may behepatotoxic, especially with prolonged use of high doses.[1]
Metandienone has highoralbioavailability.[1] It has very lowaffinity for human serumsex hormone-binding globulin (SHBG), about 10% of that of testosterone and 2% of that of DHT.[25] The drug ismetabolized in theliver by 6β-hydroxylation, 3α- and 3β-oxidation,5β-reduction, 17-epimerization, andconjugation among otherreactions.[24] Unlikemethyltestosterone, owing to the presence of its C1(2)double bond, metandienone does not produce5α-reducedmetabolites.[24][1][26] Theelimination half-life of metandienone is about 3 to 6 hours.[1][3] It iseliminated in theurine.[24]
Metandienone, also known as 17α-methyl-δ1-testosterone or as 17α-methylandrost-1,4-dien-17β-ol-3-one, is asyntheticandrostanesteroid and a17α-alkylatedderivative of testosterone.[7] It is amodification of testosterone with amethyl group at the C17α position and an additionaldouble bond between the C1 and C2 positions.[7] The drug is also the 17α-methylated derivative ofboldenone (δ1-testosterone) and the δ1analogue ofmethyltestosterone (17α-methyltestosterone).[7]
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]
Metandienone was first described in 1955.[1] It wassynthesized by researchers at theCIBA 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 apharmaceutical performance enhancement to weight lifters and other athletes.[32] Early adopters included players forOklahoma University andSan Diego Chargers head coachSid Gillman, who administered Dianabol to his team starting in 1963.[33]
After theKefauver Harris Amendment was passed in 1962, the U.S.FDA began theDESI 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 treatingpost-menopausal osteoporosis andpituitary-deficient dwarfism.[35] After CIBA'spatent exclusivity period lapsed, other manufacturers began to marketgeneric 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 theAnabolic 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 thegeneric name of the drug and itsINNTooltip International Nonproprietary Name, whilemethandienone is itsBANTooltip British Approved Name andmétandiénone is itsDCFTooltip Dénomination Commune Française.[7][4][5][6] It is also referred to asmethandrostenolone and asdehydromethyltestosterone.[7][4][5][1][6] The former synonym should not be confused withmethylandrostenolone, which is another name for a different AAS known asmetenolone.[4]
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]
Metandienone, along with other AAS, is aschedule IIIcontrolled substance in theUnited States under theControlled Substances Act.[38]
There are many known cases ofdoping in sports with metandienone byprofessionalathletes.
dianabol history.
Tablets available — Methandrostenolone Tablets usually available contain the following amounts of methandrostenolone: 2.5 and 5 mg.
