{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-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
<!--Clinical data--> | tradename = Primobolan, Primobolan S, Primonabol, Nibal | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth | class = Androgen; Anabolic steroid; Androgen ester
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!-- Identifiers --> | CAS_number_Ref = | CAS_number = 434-05-9 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 252372 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 221129 | UNII = W75590VPKQ | KEGG = | ChEBI = | ChEMBL = | synonyms = Methenolone acetate; NSC-74226; SH-567; SQ-16496; Methenolone 17β-acetate; 1-Methyl-δ<sup>1</sup>-4,5α-dihydrotestosterone 17β-acetate; 1-Methyl-δ<sup>1</sup>-DHT acetate; 1-Methylandrost-1,4-dien-17β-ol-3-one 17β-acetate
<!--Chemical data--> | 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 }} <!-- Definition and medical uses --> '''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.<ref name="Elks2014">{{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–}}</ref><ref name="IndexNominum2000">{{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}}</ref><ref name="MortonHall2012">{{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–}}</ref><ref name="Drugs.com">{{Cite web|url=https://www.drugs.com/international/metenolone.html|title=List of Androgens and anabolic steroids | work = drugs.com }}</ref><ref name="Llewellyn2011">{{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}}</ref><ref name="JamesonGroot2015">{{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–}}</ref> It is taken by mouth.<ref name="Llewellyn2011" /> Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.<ref name="Drugs.com" /><ref name="Llewellyn2011" /><ref name="IndexNominum2000" /> A related drug, metenolone enanthate, is given by injection into muscle.<ref name="Llewellyn2011" />
<!-- Side effects and mechanism --> Side effects of metenolone acetate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.<ref name="Llewellyn2011" /> 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).<ref name="Llewellyn2011" /><ref name="pmid18500378">{{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 }}</ref> It has 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 enanthate is a metenolone ester and a prodrug of metenolone in the body.<ref name="Llewellyn2011" />
<!-- History, society, and culture --> Metenolone acetate was introduced for medical use in 1961.<ref name="Publishing2013" /><ref name="Llewellyn2011" /> In addition to its medical use, metenolone acetate is used to improve physique and performance.<ref name="Llewellyn2011" /> The drug is a controlled substance in many countries and so non-medical use is generally illicit.<ref name="Llewellyn2011" /> It remains marketed for medical use only in a few countries, such as Japan and Moldova.<ref name="Drugs.com" /><ref name="Llewellyn2011" />
==Side effects== {{See also|Anabolic steroid#Adverse effects}}
==Pharmacology== {{Relative androgenic to anabolic activity in animals}}
{{Parenteral durations of androgens/anabolic steroids}}
==Chemistry== {{See also|List of androgens/anabolic steroids|List of androgen esters}}
Metenolone acetate, or metenolone 17β-acetate, is a synthetic androstane steroid and a derivative of DHT.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> It is the C17β acetate ester of metenolone, which itself is 1-methyl-δ<sup>1</sup>-4,5α-dihydrotestosterone (1-methyl-δ<sup>1</sup>-DHT) or 1-methyl-5α-androst-1-en-17β-ol-3-one.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />
{{Structural properties of major anabolic steroid esters}}
==History== Metenolone acetate was first introduced for medical use in West Germany in 1961 under the brand name Primobolan and in the United States in 1962.<ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia | edition = 3rd |url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA2109-IA118|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=2109–}}</ref><ref name="Llewellyn2011" />
==Society and culture==
===Generic names=== ''Metenolone acetate'' is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, while ''methenolone acetate'' is its {{abbrlink|USAN|United States Adopted Name}} and {{abbrlink|BANM|British Approved Name}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" /><ref name="Llewellyn2011" />
===Brand names=== Metenolone acetate is or has been marketed under a number of brand names including Primobolan, Primobolan S, Primonabol, and Nibal.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" /><ref name="Llewellyn2011" />
===Availability=== Metenolone acetate is marketed in Japan and Moldova.<ref name="Drugs.com" /><ref name="Llewellyn2011" />
== References == {{Reflist|30em}}
{{Androgens and antiandrogens}} {{Androgen receptor modulators}}
Category:Acetate esters Category:Androgen esters Category:Androgens Category:Androstanes Category:Enones