Nandrolone information

Nandrolone
Clinical data
Pronunciation	/ˈnændrəloʊn/
Trade names	• Deca-Durabolin (as NDTooltip nandrolone decanoate); • Durabolin (as NPPTooltip nandrolone phenylpropionate); • Many others (see here)
Other names	• 19-Nortestosterone; • 10-Nortestosterone; • Estr-4-en-17β-ol-3-one; • Estrenolone; • Oestrenolone; • 19-Norandrost-4-en-17β-ol-3-one; • Norandrostenolone; • Nortestrionate; • Nortestonate; • Norandroone; • SG-4341
Pregnancy; category	AU: D; ;
Routes of; administration	• IM injection (esters); • SC injection (esters); • Eye drops (NSTooltip nandrolone sulfate)
Drug class	Androgen; Anabolic steroid; Progestogen
ATC code	A14AB01 (WHO) S01XA11 (WHO);
Legal status
Legal status	BR: Class C5 (Anabolic steroids); CA: Schedule IV; UK: Class C; US: Schedule III;
Pharmacokinetic data
Bioavailability	• Oral: <3% (pigs); • Intramuscular: high
Metabolism	Liver (reduction)
Metabolites	• 5α-Dihydronandrolone; • 19-Norandrosterone; • 19-Noretiocholanolone; • Conjugates
Elimination half-life	• Nandrolone: <4.3 hours; • NDTooltip Nandrolone decanoate (IMTooltip Intramuscular injection): 6–12 days; • NPPTooltip Nandrolone phenylpropionate: 2.7 days
Duration of action	• ND (IM): 2–3 weeks; • NPP (IM): 5–7 days
Excretion	Urine
Identifiers
	IUPAC name (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	434-22-0 ;
PubChem CID	9904;
IUPHAR/BPS	6949;
DrugBank	DB13169;
ChemSpider	9520 ;
UNII	6PG9VR430D;
ChEBI	CHEBI:7466 ;
ChEMBL	ChEMBL757 ;
CompTox Dashboard (EPA)	DTXSID7023350 ;
ECHA InfoCard	100.006.457
Chemical and physical data
Formula	C18H26O2
Molar mass	274.404 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4;
	InChI 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 ; Key:NPAGDVCDWIYMMC-IZPLOLCNSA-N ;
	(verify)

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone.^{[citation needed]} 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.

[1] "Nandrolone Meaning in the Cambridge English Dictionary".

[Elks2014-2] ^ ^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.

[MortonHall2012-3] Cite error: The named reference MortonHall2012 was invoked but never defined (see the help page).

[4] 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.

[McEvoyMcVeigh1998-5] 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.

[Becker2001-6] Becker KL (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185–. ISBN 978-0-7817-1750-2.

[Label-NZ-7] ^ ^a ^b ^c ^d ^e ^f ^g "Deca-Durabolin" (PDF). Schering-Plough. Archived from the original (PDF) on 18 December 2010.

[Llewellyn2011-8] ^ ^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.

[Thomas2012-9] Thomas JA (6 December 2012). Drugs, Athletes, and Physical Performance. Springer Science & Business Media. pp. 27–29. ISBN 978-1-4684-5499-4.

[pmid9103484-10] 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.

[Label-AU-11] "Deca-Durabolin" (PDF). Merck Sharp & Dohme (Australia).

[IndexNominum2000-12] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–. ISBN 978-3-88763-075-1.

[Sneader2005-13] Sneader W (23 June 2005). Drug Discovery: A History. John Wiley & Sons. pp. 206–. ISBN 978-0-471-89979-2.

[SinghTurner2014-14] 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.

[pmid18500378-15] 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.

[Kochakian2012-16] Kochakian CD (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 401–. ISBN 978-3-642-66353-6.

[JamesonGroot2015-17] 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.

Nandrolone information

and 26 Related for: Nandrolone information

Nandrolone

Nandrolone decanoate

Nandrolone phenylpropionate

List of androgen esters

Trenbolone

Nandrolone undecanoate

List of doping cases in sport by substance

Nandrolone hexyloxyphenylpropionate

Nandrolone laurate

Nandrolone furylpropionate

Anabolic steroid

Nandrolone nonanoate

Nandrolone formate

Nandrolone cyclotate

Androgen ester

Nandrolone propionate

Trenbolone acetate

Petr Korda

Nandrolone cypionate

Nandrolone acetate

Nandrolone caproate

Bolandione

Trenbolone enanthate

Nandrolone sulfate

Nandrolone cyclohexylpropionate

List of androgens and anabolic steroids

Clinical data


Pronunciation	/ˈnændrəloʊn/^[1]
Trade names	• Deca-Durabolin (as NDTooltip nandrolone decanoate) • Durabolin (as NPPTooltip 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	AU: D
Routes of administration	• IM injection (esters) • SC injection (esters) • Eye drops (NSTooltip nandrolone sulfate)
Drug class	Androgen; Anabolic steroid; Progestogen
ATC code	A14AB01 (WHO) S01XA11 (WHO)
Legal status
Legal status	BR: Class C5 (Anabolic steroids)^[4] CA: Schedule IV UK: Class C US: Schedule III
Pharmacokinetic data
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] • NDTooltip Nandrolone decanoate (IMTooltip Intramuscular injection): 6–12 days^[7]^[8]^[10] • NPPTooltip 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]
Identifiers
IUPAC name (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	434-22-0^Y
PubChem CID	9904
IUPHAR/BPS	6949
DrugBank	DB13169
ChemSpider	9520^Y
UNII	6PG9VR430D
ChEBI	CHEBI:7466^Y
ChEMBL	ChEMBL757^Y
CompTox Dashboard (EPA)	DTXSID7023350
ECHA InfoCard	100.006.457
Chemical and physical data
Formula	C₁₈H₂₆O₂
Molar mass	274.404 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4
InChI 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^Y Key:NPAGDVCDWIYMMC-IZPLOLCNSA-N^Y
(verify)