Metenolone

Last updated
Metenolone
Metenolone.svg
Clinical data
Trade names Primobolan, Nibal (as metenolone acetate); Primobolan Depot, Nibal Injection (as metenolone enanthate)
Other namesMethenolone; Methylandrostenolone; 1-Methyl-δ1-4,5α-dihydrotestosterone; 1-Methyl-δ1-DHT; 1-Methyl-5α-androst-1-en-17β-ol-3-one
AHFS/Drugs.com International Drug Names
Routes of
administration 		By mouth (as metenolone acetate), intramuscular injection (as metenolone enanthate)
Drug class Androgen; Anabolic steroid
ATC code
Legal status
Legal status
Identifiers
  • (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-1,10,13-trimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.005.285 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H30O2
Molar mass 302.458 g·mol−1
3D model (JSmol)
  • O=C2\C=C(\C)[C@@]3([C@H]1CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]1CC[C@H]3C2)C)C
  • InChI=1S/C20H30O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h10,13,15-18,22H,4-9,11H2,1-3H3/t13-,15-,16-,17-,18-,19-,20-/m0/s1 Yes check.svgY
  • Key:ANJQEDFWRSLVBR-VHUDCFPWSA-N Yes check.svgY

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). [2] [3] [4] [5] [6] Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure. [7] Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle. [6]

Contents

Side effects of metenolone esters include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. [6] 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). [6] [8] They have moderate anabolic effects and weak androgenic effects, as well as no estrogenic effects or risk of liver damage. [6] [8] Metenolone esters are androgen esters and prodrugs of metenolone in the body. [6]

Metenolone esters were introduced for medical use in the early 1960s. [6] In addition to their medical use, metenolone esters are used to improve physique and performance. [6] The drugs are controlled substances in many countries and so non-medical use is generally illicit. [6] They have mostly been discontinued for medical use and have limited availability. [5] [6]

Medical uses

Metenolone, as its esters, is used almost exclusively in the treatment of anemia due to bone marrow failure. [7] It has also been used to treat wasting syndromes due to major surgery, infection, long-term corticosteroid therapy, malnutrition, or other causes. [6] 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. [6]

Side effects

Side effects of metenolone and its esters include virilization among others. [6]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
MedicationRatioa
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
Metenolone1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes:a = Ratio of androgenic to anabolic activity. Sources: See template.

Due to its double bond between the C1 and C2 positions, metenolone is resistant to metabolism by 3α-hydroxysteroid dehydrogenase (3α-HSD). [6] As such, unlike DHT and the closely related DHT derivatives mestanolone (17α-methyl-DHT) and mesterolone (1α-methyl-DHT), metenolone has considerable anabolic effects. [6]

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. [9]

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). [2] [3] [6] A closely related AAS is mesterolone (1α-methyl-DHT). [2] [3] [6]

Society and culture

Generic names

Metenolone is the generic name of the drug and its INN, while methenolone is its BAN. [2] [3] [4] [5] It has also been referred to as methylandrostenolone. [3] [5] This synonym should not be confused with methandrostenolone, which is another name for a different AAS known as metandienone. [10]

Doping in sports

Metenolone and its esters are banned from use in sports governed by the World Anti-Doping Agency. [11] 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.

Related Research Articles

<span class="mw-page-title-main">Methyltestosterone</span> Chemical compound

Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low doses as a component of menopausal hormone therapy for menopausal symptoms like hot flashes, osteoporosis, and low sexual desire in women, and to treat breast cancer in women. It is taken by mouth or held in the cheek or under the tongue.

<span class="mw-page-title-main">Oxandrolone</span> Androgen and anabolic steroid

Oxandrolone, sold under the brand names Oxandrin and Anavar, among others, is an androgen and anabolic steroid (AAS) medication which is used to help promote weight gain in various situations, to help offset protein catabolism caused by long-term corticosteroid therapy, to support recovery from severe burns, to treat bone pain associated with osteoporosis, to aid in the development of girls with Turner syndrome, and for other indications. It is taken by mouth.

<span class="mw-page-title-main">Oxymetholone</span> Androgen and anabolic steroid

Oxymetholone, sold under the brand names Anadrol and Anapolon among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemia. It is also used to treat osteoporosis, HIV/AIDS wasting syndrome, and to promote weight gain and muscle growth in certain situations. It is taken by mouth.

<span class="mw-page-title-main">Metandienone</span> Androgen and anabolic steroid

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. It is also used non-medically for physique- and performance-enhancing purposes. It is often taken by mouth.

<span class="mw-page-title-main">Testosterone enanthate</span> Chemical compound

Testosterone enanthate is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It is also used in hormone therapy for transgender men. It is given by injection into muscle or subcutaneously usually once every one to four weeks.

<span class="mw-page-title-main">Metenolone enanthate</span> Chemical compound

Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is given by injection into muscle. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market. A related drug, metenolone acetate, is taken by mouth.

<span class="mw-page-title-main">Mesterolone</span> Chemical compound

Mesterolone, sold under the brand name Proviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels. It has also been used to treat male infertility, although this use is controversial. It is taken by mouth.

<span class="mw-page-title-main">Fluoxymesterone</span> Chemical compound

Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia. It is taken by mouth.

<span class="mw-page-title-main">Drostanolone propionate</span> Chemical compound

Drostanolone propionate, or dromostanolone propionate, sold under the brand names Drolban, Masteril, and Masteron among others, is an androgen and anabolic steroid (AAS) medication which was used to treat breast cancer in women but is now no longer marketed. It is given by injection into muscle.

<span class="mw-page-title-main">Mestanolone</span> Chemical compound

Mestanolone, also known as methylandrostanolone and sold under the brand names Androstalone and Ermalone among others, is an androgen and anabolic steroid (AAS) medication which is mostly no longer used. It is still available for use in Japan however. It is taken by mouth.

<span class="mw-page-title-main">Drostanolone</span> Chemical compound

Drostanolone, or dromostanolone, is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed. An androgen ester prodrug of drostanolone, drostanolone propionate, was formerly used in the treatment of breast cancer in women under brand names such as Drolban, Masteril, and Masteron. This has also been used non-medically for physique- or performance-enhancing purposes.

<span class="mw-page-title-main">Anabolic steroid</span> Steroidal androgen that is structurally related and has similar effects to testosterone

Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor. Anabolic steroids have a number of medical uses, but are also used by athletes to increase muscle size, strength, and performance.

<span class="mw-page-title-main">1-Testosterone</span> Chemical compound

1-Testosterone, also known as δ1-dihydrotestosterone (δ1-DHT), as well as dihydroboldenone, is a synthetic anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of boldenone (Δ1-testosterone). It differs from testosterone by having a 1(2)-double bond instead of a 4(5)-double bond in its A ring. It was legally sold online in the United States until 2005, when it was reclassified as a Schedule III drug.

<span class="mw-page-title-main">Stenbolone</span> Chemical compound

Stenbolone is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed. A C17β ester prodrug of stenbolone, stenbolone acetate, is used as an AAS for depot intramuscular injection under the brand names Anatrofin and Stenobolone.

<span class="mw-page-title-main">Boldenone undecylenate</span> Chemical compound

Boldenone undecylenate, or boldenone undecenoate, sold under the brand names Equipoise and Parenabol among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, mainly in horses. It was formerly used in humans as well. It is given by injection into muscle.

<span class="mw-page-title-main">Stenbolone acetate</span> Chemical compound

Stenbolone acetate (USAN), also known as 2-methyl-4,5α-dihydro-δ1-testosterone 17β-acetate or as 2-methyl-5α-androst-1-en-17β-ol-3-one 17β-acetate, is a synthetic, injected anabolic–androgenic steroid (AAS) and derivative of dihydrotestosterone (DHT) which has been marketed in Spain.

<span class="mw-page-title-main">Metenolone acetate</span> Chemical compound

Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone enanthate, is given by injection into muscle.

<span class="mw-page-title-main">Androstanolone</span> Androgenic and anabolic steroid medication

Androstanolone, or stanolone, also known as dihydrotestosterone (DHT) and sold under the brand name Andractim among others, is an androgen and anabolic steroid (AAS) medication and hormone which is used mainly in the treatment of low testosterone levels in men. It is also used to treat breast development and small penis in males. Compared to testosterone, androstanolone (DHT) is less likely to aromatize into estrogen, and therefore it shows less pronounced estrogenic side effects, such as gynecomastia and water retention. On the other hand, androstanolone (DHT) show more significant androgenic side effects, such as acne, hair loss and prostate enlargement.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

References

  1. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  2. 1 2 3 4 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 784–. ISBN   978-1-4757-2085-3.
  3. 1 2 3 4 5 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–660. ISBN   978-3-88763-075-1.
  4. 1 2 Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 178–. ISBN   978-94-011-4439-1.
  5. 1 2 3 4 "List of Androgens and anabolic steroids". Drugs.com.
  6. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 625–, 633–. ISBN   978-0-9828280-1-4.
  7. 1 2 Handelsman DJ (25 February 2015). "Androgen Physiology, Pharmacology, and Abuse". In Jameson JL, De Groot LJ (eds.). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. pp. 2388–. ISBN   978-0-323-32195-2.
  8. 1 2 Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC   2439524 . PMID   18500378.
  9. ↑ 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): 2100–2106. doi:10.1210/endo-114-6-2100. PMID   6539197.
  10. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. p. 660. ISBN   978-3-88763-075-1.
  11. ↑ "The World Anti-Doping Code: The 2012 Prohibited List" (PDF). World Anti-Doping Agency. Archived from the original (PDF) on 2012-05-13. Retrieved 2012-05-10.
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