Nandrolone decanoate

Nandrolone decanoate
Clinical data
Trade namesRolon, Deca-Durabolin, others
Other names• Nandrolone decylate
• 19-Nortestosterone 17β-decanoate
Pregnancy
category
  • AU: D
Routes of
administration		Intramuscular injection, subcutaneous injection
Drug classAndrogen; Anabolic steroid; Androgen ester; Progestogen
Legal status
Legal status
Pharmacokinetic data
BioavailabilityIntramuscular: 53–73%[1]
MetabolismBlood (hydrolysis), liver (reduction)[2][4]
Metabolites• Nandrolone[2][3]
• 5α-Dihydronandrolone[2][3]
• 19-Norandrosterone[2]
• 19-Noretiocholanolone[2]
• Conjugates[4]
Elimination half-life• Intramuscular: 6–12 days[2][5]
• Nandrolone: <4.3 hours[2]
Duration of action• Intramuscular: 2–3 weeks[3][6]
ExcretionUrine[2]
Identifiers
  • [(8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] decanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.006.037 Edit this at Wikidata
Chemical and physical data
FormulaC28H44O3
Molar mass428.657 g·mol−1
3D model (JSmol)
  • CCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C
  • InChI=1S/C28H44O3/c1-3-4-5-6-7-8-9-10-27(30)31-26-16-15-25-24-13-11-20-19-21(29)12-14-22(20)23(24)17-18-28(25,26)2/h19,22-26H,3-18H2,1-2H3/t22-,23+,24+,25-,26-,28-/m0/s1
  • Key:JKWKMORAXJQQSR-MOPIKTETSA-N

Nandrolone decanoate, sold under the brand names Rolon[7] and Deca-Durabolin, among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemias and wasting syndromes, as well as osteoporosis in menopausal women.[8][9][10][11][3] It is given by injection into muscle or fat once every one to four weeks.[3][12]

Side effects of nandrolone decanoate may include symptoms of masculinization like acne, increased hair growth, and voice changes.[3] The medication 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).[3][13] It has strong anabolic effects and weak androgenic effects, which give it a mild side effect profile and make it especially suitable for use in women and children.[3][13][14] Nandrolone decanoate is a nandrolone ester and a long-lasting prodrug of nandrolone in the body.[3][15]

Nandrolone decanoate was first described in 1960 and was introduced for medical use in 1962.[3] It was the second nandrolone ester to be introduced, following nandrolone phenylpropionate (NPP) in 1959, and is one of the most widely used nandrolone esters.[3][16] It is also one of the most widely used AAS worldwide.[3] In addition to its medical use, nandrolone decanoate is used to improve physique and performance, and is said to be the most widely used AAS for such purposes.[3][17] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[3]

  1. ^ Bagchus WM, Smeets JM, Verheul HA, De Jager-Van Der Veen SM, Port A, Geurts TB (May 2005). "Pharmacokinetic evaluation of three different intramuscular doses of nandrolone decanoate: analysis of serum and urine samples in healthy men". The Journal of Clinical Endocrinology and Metabolism. 90 (5): 2624–2630. doi:10.1210/jc.2004-1526. PMID 15713722.
  2. ^ a b c d e f g h "ROLON IN" (PDF). medsafe.govt.nz. Archived from the original (PDF) on 28 January 2018. Retrieved 15 January 2022.
  3. ^ a b c d e f g h i j k l m n Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 402–412, 193–194. ISBN 978-0-9828280-1-4.
  4. ^ a b Cite error: The named reference Thomas2012 was invoked but never defined (see the help page).
  5. ^ Minto CF, Howe C, Wishart S, Conway AJ, Handelsman DJ (April 1997). "Pharmacokinetics and pharmacodynamics of nandrolone esters in oil vehicle: effects of ester, injection site and injection volume". The Journal of Pharmacology and Experimental Therapeutics. 281 (1): 93–102. PMID 9103484.
  6. ^ Cite error: The named reference Label-AU was invoked but never defined (see the help page).
  7. ^ "Rolon 250mg/ml Solution for Injection - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Archived from the original on 2020-09-22. Retrieved 2020-10-09.
  8. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 660–. ISBN 978-1-4757-2085-3.
  9. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–717. ISBN 978-3-88763-075-1.
  10. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
  11. ^ "Nandrolone - FDA prescribing information, side effects and uses". Drugs.com. Retrieved 24 March 2022.
  12. ^ Singh GK, Turner L, Desai R, Jimenez M, Handelsman DJ (July 2014). "Pharmacokinetic-pharmacodynamic study of subcutaneous injection of depot nandrolone decanoate using dried blood spots sampling coupled with ultrapressure liquid chromatography tandem mass spectrometry assays". The Journal of Clinical Endocrinology and Metabolism. 99 (7): 2592–2598. doi:10.1210/jc.2014-1243. PMID 24684468.
  13. ^ a b Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  14. ^ Kochakian CD (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 401–. ISBN 978-3-642-66353-6.
  15. ^ Wijnand HP, Bosch AM, Donker CW (1985). "Pharmacokinetic parameters of nandrolone (19-nortestosterone) after intramuscular administration of nandrolone decanoate (ROLON) to healthy volunteers". Acta Endocrinologica. Supplementum. 271 (3_Suppla): 19–30. doi:10.1530/acta.0.109s00019. PMID 3865478.
  16. ^ Sneader W (23 June 2005). Drug Discovery: A History. John Wiley & Sons. pp. 206–. ISBN 978-0-471-89979-2.
  17. ^ Jameson JL, De Groot LJ (25 February 2015). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. pp. 2388–. ISBN 978-0-323-32195-2.