Metenolone

Metenolone
Clinical data
Trade names	Primobolan, Nibal (as metenolone acetate); Primobolan Depot, Nibal Injection (as metenolone enanthate)
Other names	Methenolone; 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	A14AA04 (WHO) ;
Legal status
Legal status	CA: Schedule IV ; US: Schedule III ;
Identifiers
	IUPAC name (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	153-00-4 ;
PubChem CID	3037705;
ChemSpider	2301378 ;
UNII	9062ZT8Q5C;
CompTox Dashboard (EPA)	DTXSID10165179 ;
ECHA InfoCard	100.005.285
Chemical and physical data
Formula	C20H30O2
Molar mass	302.458 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:ANJQEDFWRSLVBR-VHUDCFPWSA-N ;
	(verify)

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).[1][2][3][4][5] Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure.[6] Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.[5]

Side effects of metenolone esters include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[5] 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).[5][7] They have moderate anabolic effects and weak androgenic effects, as well as no estrogenic effects or risk of liver damage.[5][7] Metenolone esters are androgen esters and prodrugs of metenolone in the body.[5]

Metenolone esters were introduced for medical use in the early 1960s.[5] In addition to their medical use, metenolone esters are used to improve physique and performance.[5] The drugs are controlled substances in many countries and so non-medical use is generally illicit.[5] They have mostly been discontinued for medical use and have limited availability.[4][5]

Medical uses

Metenolone, as its esters, is used almost exclusively in the treatment of anemia due to bone marrow failure.[6] It has also been used to treat wasting syndromes due to major surgery, infection, long-term corticosteroid therapy, malnutrition, or other causes.[5] 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.[5]

Side effects

Side effects of metenolone and its esters include virilization among others.[5]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity
of androgens/anabolic steroids
Medication	Ratio^a
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	1:2–1:30
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).[5] As such, unlike DHT and the closely related DHT derivatives mestanolone (17α-methyl-DHT) and mesterolone (1α-methyl-DHT), metenolone has considerable anabolic effects.[5]

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.[8]

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).[1][2][5] A closely related AAS is mesterolone (1α-methyl-DHT).[1][2][5]

Society and culture

Generic names

Metenolone is the generic name of the drug and its INN, while methenolone is its BAN.[1][2][3][4] It has also been referred to as methylandrostenolone.[2][4] This synonym should not be confused with methandrostenolone, which is another name for a different AAS known as metandienone.[9]

Doping in sports

Metenolone and its esters are banned from use in sports governed by the World Anti-Doping Agency.[10] 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.

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References

J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 784–. ISBN 978-1-4757-2085-3.
Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–660. ISBN 978-3-88763-075-1.
I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 178–. ISBN 978-94-011-4439-1.
https://www.drugs.com/international/metenolone.html
William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 625–, 633–. ISBN 978-0-9828280-1-4.
J. Larry Jameson; Leslie J. De Groot (25 February 2015). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. pp. 2388–. ISBN 978-0-323-32195-2.
Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
Saartok T, Dahlberg E, Gustafsson JA (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. PMID 6539197.
Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. p. 660. ISBN 978-3-88763-075-1.
"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.

External links

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[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 784–. ISBN 978-1-4757-2085-3.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–660. ISBN 978-3-88763-075-1.

[MortonHall2012-3] I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 178–. ISBN 978-94-011-4439-1.

[Drugs.com-4] ttps://www.drugs.com/international/metenolone.html

[Llewellyn2011-5] William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 625–, 633–. ISBN 978-0-9828280-1-4.

[JamesonGroot2015-6] J. Larry Jameson; Leslie J. De Groot (25 February 2015). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. pp. 2388–. ISBN 978-0-323-32195-2.

[pmid18500378-7] Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.

[pmid6539197-8] Saartok T, Dahlberg E, Gustafsson JA (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. PMID 6539197.

[IndexNominum2000-2-9] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. p. 660. ISBN 978-3-88763-075-1.

[10] "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.