View source for Metenolone enanthate

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 447451529
| 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] heptanoate
| image = Metenolone enanthate.png
| image_class = skin-invert-image
| width = 250px

<!--Clinical data-->
| tradename = Nibal Injection, Primobolan Depot
| 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 = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = Schedule III
| legal_status = 
| routes_of_administration = [[Intramuscular injection]]
| class = [[Androgen]]; [[Anabolic steroid]]; [[Androgen ester]]

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = {{abbrlink|IM|Intramuscular injection}}: 10.5 days<ref name="RuizStrain2011">{{cite book| vauthors = Westreich LM | chapter = Anabolic-Androgenic Steroids| veditors = Ruiz P, Strain EC |title=Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook | chapter-url = https://books.google.com/books?id=w4ZUJAdleTsC&pg=PA358 |year=2011|publisher=Lippincott Williams & Wilkins|isbn=978-1-60547-277-5|pages=358–}}</ref>
| excretion = 

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 303-42-4
| ATC_prefix = 
| ATC_suffix = 
| PubChem = 248271
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 217360
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 0SPD480WFH
| synonyms = Methenolone enanthate; Metenolone heptanoate; Metenolone 17β-enanthate; NSC-64967; SH-601; SQ-16374; 1-Methyl-4,5α-dihydrotestosterone 17β-heptanoate; 1-Methyl-DHT heptanoate; 1-Methyl-5α-androst-1-en-17β-ol-3-one 17β-heptanoate

<!--Chemical data-->
| C=27 | H=42 | O=3 
| SMILES = O=C2\C=C(\C)[C@@]3([C@H]1CC[C@@]4([C@@H](OC(=O)CCCCCC)CC[C@H]4[C@@H]1CC[C@H]3C2)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C27H42O3/c1-5-6-7-8-9-25(29)30-24-13-12-22-21-11-10-19-17-20(28)16-18(2)27(19,4)23(21)14-15-26(22,24)3/h16,19,21-24H,5-15,17H2,1-4H3/t19-,21-,22-,23-,24-,26-,27-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TXUICONDJPYNPY-FRXWOFFRSA-N
}}
<!-- Definition and medical uses -->
'''Metenolone enanthate''', or '''methenolone enanthate''', sold under the brand names '''Primobolan Depot''' and '''Nibal Injection''', 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}}</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=633–}}</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 given by [[intramuscular injection|injection into muscle]].<ref name="Llewellyn2011" /> Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market.<ref name="Drugs.com" /><ref name="Llewellyn2011" /><ref name="IndexNominum2000" /> A related drug, [[metenolone acetate]], is taken [[oral administration|by mouth]].<ref name="Llewellyn2011" />

<!-- Side effects and mechanism -->
[[Side effect]]s of metenolone enanthate include [[symptom]]s of [[virilization|masculinization]] like [[acne]], [[hirsutism|increased hair growth]], [[voice deepening|voice changes]], and increased [[libido|sexual desire]].<ref name="Llewellyn2011" /> The drug is a [[synthetic compound|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 = Br. J. Pharmacol. | volume = 154 | issue = 3 | pages = 502–21 | year = 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref> It has moderate [[anabolic]] effects and weak [[androgen]]ic effects, as well as no [[estrogen (medication)|estrogen]]ic effects or risk of [[hepatotoxicity|liver damage]].<ref name="Llewellyn2011" /><ref name="pmid18500378" /> Metenolone enanthate is a [[metenolone ester]] and a long-lasting [[prodrug]] of [[metenolone]] in the body.<ref name="Llewellyn2011" />

<!-- History, society, and culture -->
Metenolone enanthate was introduced for medical use in 1962.<ref name="Llewellyn2011" /> In addition to its medical use, metenolone enanthate is used to [[performance-enhancing substance|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 [[Spain]] and [[Turkey]].<ref name="Drugs.com" /><ref name="Llewellyn2011" />

==Medical uses==
Metenolone enanthate has been studied in the treatment of [[breast cancer]].<ref name="KennedyYarbro1968">{{cite journal | vauthors = Kennedy BJ, Yarbro JW | title = Effect of methenolone enanthate (NSC-64967) in advanced cancer of the breast | journal = Cancer | volume = 21 | issue = 2 | pages = 197–201 | date = February 1968 | pmid = 4952912 | doi = 10.1002/1097-0142(196802)21:2<197::AID-CNCR2820210207>3.0.CO;2-R | doi-access = free }}</ref><ref name="Notter1975">{{cite journal | vauthors = Notter G | title = Treatment of disseminated carcinoma of the breast by metenolone enanthate | journal = Acta Radiologica | volume = 14 | issue = 6 | pages = 545–551 | date = December 1975 | pmid = 1224996 | doi = 10.3109/02841867509132696 | doi-access = free }}</ref>

==Side effects==
{{See also|Anabolic steroid#Adverse effects}}

==Pharmacology==

===Pharmacodynamics===
{{Relative androgenic to anabolic activity in animals}}

As a derivative of DHT, metenolone, the active form of metenolone enanthate, is not [[aromatase|aromatized]], and so has no propensity for producing [[estrogen (medication)|estrogen]]ic [[side effect]]s like [[gynecomastia]].<ref name="Llewellyn2011" /> As an AAS, metenolone enanthate is [[antigonadotropic]] and can suppress the [[hypothalamic–pituitary–gonadal axis]] and produce reversible [[hypogonadism]] and [[infertility]].<ref name="Llewellyn2011" /><ref name="pmid12740738">{{cite journal | journal = Int J Sports Med | date = Apr 2003 | volume = 24 | issue = 3 | pages = 195–196 | title = Androgenic anabolic steroid use and severe hypothalamic-pituitary dysfunction: a case study |vauthors=van Breda E, Keizer HA, Kuipers H, Wolffenbuttel BH | pmid= 12740738 | doi=10.1055/s-2003-39089| s2cid = 260166539 }}</ref>

===Pharmacokinetics===
The [[biological half-life]] of metenolone enanthate is reported to be about 10.5&nbsp;days by [[intramuscular injection]].<ref name="RuizStrain2011" />

{{Parenteral durations of androgens/anabolic steroids}}

==Chemistry==
{{See also|List of androgens/anabolic steroids|List of androgen esters}}

Metenolone enanthate, or metenolone 17β-enanthate, is a [[synthetic compound|synthetic]] [[androstane]] [[steroid]] and a [[chemical derivative|derivative]] of DHT.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> It is the C17β [[enanthate]] (heptanoate) [[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 enanthate was introduced for medical use in 1962 in the [[United States]] under the brand name Nibal Depot.<ref name="Llewellyn2011" /> It was soon discontinued in the United States and was marketed instead in [[Europe]] in the 1960s and 1970s under the brand name Primobolan Depot.<ref name="Llewellyn2011" />

==Society and culture==

===Generic names===
''Methenolone enanthate'' is the {{abbrlink|USAN|United States Adopted Name}} of metenolone enanthate, and ''methenolone'' is the {{abbrlink|BAN|British Approved Name}} of its active form, metenolone.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" /> Conversely, ''metenolone'' is the {{abbrlink|INN|International Nonproprietary Name}} of metenolone.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />

===Brand names===
Metenolone enanthate is or has been marketed under the brand names Nibal Injection and Primobolan Depot.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /><ref name="Drugs.com" />

===Availability===
Metenolone enanthate is marketed in [[Spain]] and [[Turkey]].<ref name="Drugs.com" /><ref name="Llewellyn2011" />

===Doping in sports===
{{See also|List of doping in sport cases#Metenolone esters}}

There are known cases of doping in sports with metenolone enanthate by [[professional sports|professional]] [[athlete]]s.

==References==
{{Reflist|30em}}

==External links==
* [https://anabolic.org/primobolan-depot-methenolone-enanthate/ Primobolan Depot (methenolone enanthate) - William Llewellyn's Anabolic.org] {{Webarchive|url=https://web.archive.org/web/20190629144018/https://anabolic.org/primobolan-depot-methenolone-enanthate/ |date=2019-06-29 }}


{{Androgens and antiandrogens}}
{{Androgen receptor modulators}}

[[Category:Androgen esters]]
[[Category:Anabolic–androgenic steroids]]
[[Category:Androstanes]]
[[Category:Enanthate esters]]
[[Category:Enones]]