Metenolone

Template:Short description Template:Distinguish Template:Drugbox Metenolone, or methenolone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as metenolone acetate (brand name Primobolan, Nibal) and metenolone enanthate (brand name Primobolan Depot, Nibal Injection).<ref name="Elks2014">Template:Cite book</ref><ref name="IndexNominum2000">Template:Cite book</ref><ref name="MortonHall2012">Template:Cite book</ref><ref name="Drugs.com">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="Llewellyn2011">Template:Cite book</ref> Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure.<ref name="JamesonGroot2015">Template:Cite book</ref> Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.<ref name="Llewellyn2011" />

Side effects of metenolone esters include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.<ref name="Llewellyn2011" /> Metenolone esters are synthetic androgens and anabolic steroids and hence are agonists of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT).<ref name="Llewellyn2011" /><ref name="pmid18500378">Template:Cite journal</ref> They have moderate anabolic effects and weak androgenic effects, as well as no estrogenic effects or risk of liver damage.<ref name="Llewellyn2011" /><ref name="pmid18500378" /> Metenolone esters are androgen esters and prodrugs of metenolone in the body.<ref name="Llewellyn2011" />

Metenolone esters were introduced for medical use in the early 1960s.<ref name="Llewellyn2011" /> In addition to their medical use, metenolone esters are used to improve physique and performance.<ref name="Llewellyn2011" /> The drugs are controlled substances in many countries and so non-medical use is generally illicit.<ref name="Llewellyn2011" /> They have mostly been discontinued for medical use and have limited availability.<ref name="Drugs.com" /><ref name="Llewellyn2011" />

Medical uses

Metenolone, as its esters, is used almost exclusively in the treatment of anemia due to bone marrow failure.<ref name="JamesonGroot2015" /> It has also been used to treat wasting syndromes due to major surgery, infection, long-term corticosteroid therapy, malnutrition, or other causes.<ref name="Llewellyn2011" /> It has also been used to treat osteoporosis and sarcopenia, to inhibit the natural loss of muscle mass with aging, and to promote weight gain in underweight premature infants and children.<ref name="Llewellyn2011" />

Side effects

Side effects of metenolone and its esters include virilization among others.<ref name="Llewellyn2011" />

Pharmacology

Pharmacodynamics

Due to its double bond between the C1 and C2 positions, metenolone is resistant to metabolism by 3α-hydroxysteroid dehydrogenase (3α-HSD).<ref name="Llewellyn2011" /> As such, unlike DHT and the closely related DHT derivatives mestanolone (17α-methyl-DHT) and mesterolone (1α-methyl-DHT), metenolone has considerable anabolic effects.<ref name="Llewellyn2011" />

Pharmacokinetics

Metenolone has very low affinity for human serum sex hormone-binding globulin (SHBG), about 16% of that of testosterone and 3% of that of DHT.<ref name="pmid6539197">Template:Cite journal</ref>

Chemistry

Metenolone, also known as 1-methyl-4,5α-dihydro-δ¹-testosterone (1-methyl-δ¹-DHT) or as 1-methyl-5α-androst-1-en-17β-ol-3-one, is a synthetic androstane steroid and derivative of dihydrotestosterone (DHT).<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> A closely related AAS is mesterolone (1α-methyl-DHT).<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />

Society and culture

Generic names

Metenolone is the generic name of the drug and its Template:Abbrlink, while methenolone is its Template:Abbrlink.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" /> It has also been referred to as methylandrostenolone.<ref name="IndexNominum2000" /><ref name="Drugs.com" /> This synonym should not be confused with methandrostenolone, which is another name for a different AAS known as metandienone.<ref name="IndexNominum2000-2">Template:Cite book</ref>

Doping in sports

Metenolone and its esters are banned from use in sports governed by the World Anti-Doping Agency.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The NBA and NBPA also banned the use of metenolone and its esters under the Anti-Drug Program. There are known cases of doping in sports with metenolone esters by professional athletes.

External links

• Primobolan (methenolone acetate) - William Llewellyn's Anabolic.org
• Primobolan Depot (methenolone enanthate) - William Llewellyn's Anabolic.org