Androgenic Anabolic steroid
Pharmaceutical compound
Nandrolone Pronunciation [ 1] Trade names • Deca-Durabolin (as ND Tooltip nandrolone decanoate ) • Durabolin (as NPP Tooltip nandrolone phenylpropionate ) • Many others (see here ) Other names • 19-Nortestosterone[ 2] [ 3] • 10-Nortestosterone • Estr-4-en-17β-ol-3-one • Estrenolone • Oestrenolone • 19-Norandrost-4-en-17β-ol-3-one • Norandrostenolone[ 2] • Nortestrionate[ 2] • Nortestonate[ 2] • Norandroone • SG-4341[ 2] [ 3] Pregnancy category Routes of administration • IM injection (esters ) • SC injection (esters ) • Eye drops (NS Tooltip nandrolone sulfate ) Drug class Androgen ; Anabolic steroid ; Progestogen ATC code Legal status
Bioavailability • Oral : <3% (pigs)[ 5] • Intramuscular : high[ 6] Metabolism Liver (reduction )[ 7] [ 9] Metabolites • 5α-Dihydronandrolone [ 7] [ 8] • 19-Norandrosterone [ 7] • 19-Noretiocholanolone [ 7] • Conjugates [ 9] Elimination half-life • Nandrolone: <4.3 hours[ 7] • ND Tooltip Nandrolone decanoate (IM Tooltip Intramuscular injection ): 6–12 days[ 7] [ 8] [ 10] • NPP Tooltip Nandrolone phenylpropionate : 2.7 days[ 10] Duration of action • ND (IM ): 2–3 weeks[ 8] [ 11] • NPP (IM ): 5–7 days[ 8] [ 10] Excretion Urine [ 7]
(8R ,9S ,10R ,13S ,14S ,17S )-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H -cyclopenta[a ]phenanthren-3-one
CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.006.457 Formula C 18 H 26 O 2 Molar mass 274.404 g·mol−1 3D model (JSmol )
O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4
InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1
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Nandrolone , also known as 19-nortestosterone , is an endogenous androgen . It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin ) and nandrolone phenylpropionate (brand name Durabolin ).[ 2] [ 12] [ 8] [ 13] Nandrolone esters are used in the treatment of anemias , cachexia (muscle wasting syndrome), osteoporosis , breast cancer , and for other indications.[ 8] They are now used by oral administration or instead are given by injection into muscle or fat .[ 8] [ 13] [ 14]
Side effects of nandrolone esters include symptoms of masculinization like acne , increased hair growth , and voice changes .[ 8] They 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).[ 8] [ 15] Nandrolone has strong anabolic effects and weak androgenic effects, which give them a mild side effect profile and make them especially suitable for use in women and children.[ 8] [ 15] [ 16] There are metabolites of Nandrolone that act as long-lasting prodrugs in the body,[ 8] such as 5α-Dihydronandrolone .
Nandrolone esters were first described and introduced for medical use in the late 1950s.[ 8] They are among the most widely used anabolic steroid worldwide.[ 8] In addition to their medical use, nandrolone esters are used to improve physique and performance , and are said to be the most widely used anabolic steroid for such purposes.[ 8] [ 17] The drugs are controlled substances in many countries and so non-medical use is generally illicit.[ 8]
^ "Nandrolone Meaning in the Cambridge English Dictionary" .
^ a b c d e f Elks J, Ganellin CR, eds. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . New York City: Springer. pp. 660–. ISBN 978-1-4757-2085-3 . OCLC 1079003025 .
^ a b Cite error: The named reference MortonHall2012
was invoked but never defined (see the help page ).
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15 .
^ McEvoy JD, McVeigh CE, McCaughey WJ (December 1998). "Residues of nortestosterone esters at injection sites. Part 1. Oral bioavailability". The Analyst . 123 (12): 2475–8. doi :10.1039/a804919j . PMID 10435281 .
^ Becker KL (2001). Principles and Practice of Endocrinology and Metabolism . Lippincott Williams & Wilkins. pp. 1185–. ISBN 978-0-7817-1750-2 .
^ a b c d e f g "Deca-Durabolin" (PDF) . Schering-Plough . Archived from the original (PDF) on 18 December 2010.
^ a b c d e f g h i j k l m n o Llewellyn W (2011). Anabolics . Molecular Nutrition Llc. pp. 402–412, 460–467, 193–194. ISBN 978-0-9828280-1-4 .
^ a b Thomas JA (6 December 2012). Drugs, Athletes, and Physical Performance . Springer Science & Business Media. pp. 27–29. ISBN 978-1-4684-5499-4 .
^ a b c 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 .
^ "Deca-Durabolin" (PDF) . Merck Sharp & Dohme (Australia) .
^ Index Nominum 2000: International Drug Directory . Taylor & Francis. January 2000. pp. 716–. ISBN 978-3-88763-075-1 .
^ a b Sneader W (23 June 2005). Drug Discovery: A History . John Wiley & Sons. pp. 206–. ISBN 978-0-471-89979-2 .
^ 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): 2592–8. doi :10.1210/jc.2014-1243 . PMID 24684468 .
^ a b Kicman AT (June 2008). "Pharmacology of anabolic steroids" . British Journal of Pharmacology . 154 (3): 502–21. doi :10.1038/bjp.2008.165 . PMC 2439524 . PMID 18500378 .
^ Kochakian CD (6 December 2012). Anabolic-Androgenic Steroids . Springer Science & Business Media. pp. 401–. ISBN 978-3-642-66353-6 .
^ 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 .