Metenolone acetate

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = [(5S,8R,9S,10S,13S,14S,17S)-1,10,13-Trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate

| image = Metenolone acetate.svg

| image_class = skin-invert-image

| width = 225px

| tradename = Primobolan, Primobolan S, Primonabol, Nibal

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| routes_of_administration = By mouth

| class = Androgen; Anabolic steroid; Androgen ester

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| CAS_number = 434-05-9

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| PubChem = 252372

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| ChemSpiderID = 221129

| UNII = W75590VPKQ

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| synonyms = Methenolone acetate; NSC-74226; SH-567; SQ-16496; Methenolone 17β-acetate; 1-Methyl-δ¹-4,5α-dihydrotestosterone 17β-acetate; 1-Methyl-δ¹-DHT acetate; 1-Methylandrost-1,4-dien-17β-ol-3-one 17β-acetate

| C=22 | H=32 | O=3

| SMILES = CC1=CC(=O)C[C@H]2[C@]1([C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4OC(=O)C)C)C

| StdInChI_Ref =

| StdInChI = 1S/C22H32O3/c1-13-11-16(24)12-15-5-6-17-18-7-8-20(25-14(2)23)21(18,3)10-9-19(17)22(13,15)4/h11,15,17-20H,5-10,12H2,1-4H3/t15-,17-,18-,19-,20-,21-,22-/m0/s1

| StdInChIKey_Ref =

| StdInChIKey = PGAUJQOPTMSERF-QWQRBHLCSA-N

}}

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.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA784|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=784–}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA660|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=659–661}}{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA178|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=178–}}{{Cite web|url=https://www.drugs.com/international/metenolone.html|title=List of Androgens and anabolic steroids | work = drugs.com }}{{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT625|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=625–632}}{{cite book| vauthors = Handelsman DJ | chapter = Androgen Physiology, Pharmacology, and Abuse| veditors = Jameson JL, De Groot LJ |title=Endocrinology: Adult and Pediatric E-Book| chapter-url = https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PA2388 |date=25 February 2015|publisher=Elsevier Health Sciences|isbn=978-0-323-32195-2|pages=2388–}} 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.

Side effects of metenolone acetate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT).{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–521 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }} It has moderate anabolic effects and weak androgenic effects, as well as no estrogenic effects or risk of liver damage. Metenolone enanthate is a metenolone ester and a prodrug of metenolone in the body.

Metenolone acetate was introduced for medical use in 1961. In addition to its medical use, metenolone acetate is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit. It remains marketed for medical use only in a few countries, such as Japan and Moldova.