Metenolone enanthate

Metenolone enanthate
Clinical data
Trade namesNibal Injection, Primobolan Depot
Other namesMethenolone 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
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
Legal status
Legal status
Pharmacokinetic data
Elimination half-lifeIMTooltip Intramuscular injection: 10.5 days[1]
Identifiers
  • [(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
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.005.584 Edit this at Wikidata
Chemical and physical data
FormulaC27H42O3
Molar mass414.630 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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 checkY
  • Key:TXUICONDJPYNPY-FRXWOFFRSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.[2][3][4][5][6][7] It is given by injection into muscle.[6] 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.[5][6][3] A related drug, metenolone acetate, is taken by mouth.[6]

Side effects of metenolone enanthate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[6] 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).[6][8] It has moderate anabolic effects and weak androgenic effects, as well as no estrogenic effects or risk of liver damage.[6][8] Metenolone enanthate is a metenolone ester and a long-lasting prodrug of metenolone in the body.[6]

Metenolone enanthate was introduced for medical use in 1962.[6] In addition to its medical use, metenolone enanthate is used to improve physique and performance.[6] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[6] It remains marketed for medical use only in a few countries, such as Spain and Turkey.[5][6]

  1. ^ Westreich LM (2011). "Anabolic-Androgenic Steroids". In Ruiz P, Strain EC (eds.). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. pp. 358–. ISBN 978-1-60547-277-5.
  2. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 784–. ISBN 978-1-4757-2085-3.
  3. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–661. ISBN 978-3-88763-075-1.
  4. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 178–. ISBN 978-94-011-4439-1.
  5. ^ a b c "List of Androgens and anabolic steroids".
  6. ^ a b c d e f g h i j k l William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 633–. ISBN 978-0-9828280-1-4.
  7. ^ Handelsman DJ (25 February 2015). "Androgen Physiology, Pharmacology, and Abuse". In Jameson JL, De Groot LJ (eds.). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. pp. 2388–. ISBN 978-0-323-32195-2.
  8. ^ a b Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.