metenolone

{{Short description|Chemical compound}}

{{Distinguish|metandienone (methandrostenolone)}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid =

| 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

| image = Metenolone.svg

| image_class = skin-invert-image

| width = 225px

| tradename = Primobolan, Nibal (as metenolone acetate); Primobolan Depot, Nibal Injection (as metenolone enanthate)

| Drugs.com = {{drugs.com|international|metenolone}}

| pregnancy_category =

| legal_BR = C5

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA = Schedule IV

| legal_US = Schedule III

| legal_status =

| routes_of_administration = By mouth (as metenolone acetate), intramuscular injection (as metenolone enanthate)

| class = Androgen; Anabolic steroid

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 153-00-4

| ATC_prefix = A14

| ATC_suffix = AA04

| PubChem = 3037705

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2301378

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9062ZT8Q5C

| synonyms = Methenolone; Methylandrostenolone; 1-Methyl-δ¹-4,5α-dihydrotestosterone; 1-Methyl-δ¹-DHT; 1-Methyl-5α-androst-1-en-17β-ol-3-one

| C=20 | H=30 | O=2

| 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ANJQEDFWRSLVBR-VHUDCFPWSA-N

}}

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).{{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=659–660}}{{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–,633–}} Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure.{{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–}} Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.

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

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