metenolone enanthate

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 447451529

| 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] heptanoate

| image = Metenolone enanthate.png

| image_class = skin-invert-image

| width = 250px

| tradename = Nibal Injection, Primobolan Depot

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US = Schedule III

| legal_status =

| routes_of_administration = Intramuscular injection

| class = Androgen; Anabolic steroid; Androgen ester

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life = {{abbrlink|IM|Intramuscular injection}}: 10.5 days{{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–}}

| excretion =

| 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

| 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

}}

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.{{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}}{{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–}}{{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 given by injection into muscle. 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. A related drug, metenolone acetate, is taken by mouth.

Side effects of metenolone enanthate 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 = Br. J. Pharmacol. | volume = 154 | issue = 3 | pages = 502–21 | year = 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 long-lasting prodrug of metenolone in the body.

Metenolone enanthate was introduced for medical use in 1962. In addition to its medical use, metenolone enanthate 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 Spain and Turkey.

Medical uses

Metenolone enanthate has been studied in the treatment of breast cancer.{{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 }}{{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 }}

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 aromatized, and so has no propensity for producing estrogenic side effects like gynecomastia. As an AAS, metenolone enanthate is antigonadotropic and can suppress the hypothalamic–pituitary–gonadal axis and produce reversible hypogonadism and infertility.{{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 }}

=Pharmacokinetics=

The biological half-life of metenolone enanthate is reported to be about 10.5 days by intramuscular injection.

{{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 androstane steroid and a derivative of DHT. It is the C17β enanthate (heptanoate) ester of metenolone, which itself is 1-methyl-δ1-4,5α-dihydrotestosterone (1-methyl-δ1-DHT) or 1-methyl-5α-androst-1-en-17β-ol-3-one.

{{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. 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.

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. Conversely, metenolone is the {{abbrlink|INN|International Nonproprietary Name}} of metenolone.

=Brand names=

Metenolone enanthate is or has been marketed under the brand names Nibal Injection and Primobolan Depot.

=Availability=

Metenolone enanthate is marketed in Spain and Turkey.

=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 athletes.

References

{{Reflist|30em}}