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(Top) 1 Medical uses 2 Side effects 3 Pharmacology 3.1 Pharmacodynamics 3.2 Pharmacokinetics 4 Chemistry 5 Society and culture 5.1 Generic names 5.2 Doping in sports 6 References 7 External links

Metenolone

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Metenolone
Clinical data

Trade names	Primobolan, Nibal (asmetenolone acetate); Primobolan Depot, Nibal Injection (asmetenolone 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 (asmetenolone acetate), intramuscular injection (asmetenolone enanthate)
Drug class	Androgen; Anabolic steroid
ATC code	A14AA04 (WHO)
Legal status
Legal status	BR: Class C5 (Anabolic steroids)^[1] 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^Y
PubChem CID	3037705
ChemSpider	2301378^Y
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^Y Key:ANJQEDFWRSLVBR-VHUDCFPWSA-N^Y

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]

Side effects of metenolone esters include symptomsofmasculinization 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

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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

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

Pharmacology

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Pharmacodynamics

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v

t

e
Androgenic vs. anabolic activity ratio
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 metabolismby3α-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

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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

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

Society and culture

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Generic names

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Metenolone is the generic name of the drug and its INNTooltip International Nonproprietary Name, while methenolone is its BANTooltip British Approved Name.^[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

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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.

References

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^ 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.

^ ^a ^b ^c ^d 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.

^ ^a ^b ^c ^d ^e Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–660. ISBN 978-3-88763-075-1.

^ ^a ^b 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.

^ ^a ^b ^c ^d "List of Androgens and anabolic steroids". Drugs.com.

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 625–, 633–. ISBN 978-0-9828280-1-4.

^ ^a ^b 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.

^ ^a ^b 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.

^ 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.

^ 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.