Norethandrolone

Norethandrolone
Clinical data
Trade names	Nilevar, Pronabol
Other names	Noretandrolone; CB-8022; 3-Ketoethylestrenol; Ethylestrenolone; 17α-Ethyl-19-nortestosterone; 17α-Ethylestr-4-en-17β-ol-3-one; 17α-Ethyl-19-norandrost-4-en-17β-ol-3-one; Ethylnandrolone; Ethylnortestosterone
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth
Drug class	Androgen; Anabolic steroid; Progestin; Progestogen
ATC code	A14AA09 (WHO) ;
Legal status
Legal status	BR: Class C5 (Anabolic steroids); CA: Schedule IV; US: Schedule III;
Identifiers
	IUPAC name (8R,9S,10R,13S,14S,17S)-17-ethyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one;
CAS Number	52-78-8 ;
PubChem CID	5858;
ChemSpider	5649 ;
UNII	P7W01638W6;
KEGG	D07127 ;
CompTox Dashboard (EPA)	DTXSID0023379 ;
ECHA InfoCard	100.000.140
Chemical and physical data
Formula	C20H30O2
Molar mass	302.458 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)CC)[C@@H]2CC3)C)CC4;
	InChI InChI=1S/C20H30O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h12,15-18,22H,3-11H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1 ; Key:ZDHCJEIGTNNEMY-XGXHKTLJSA-N ;
	(verify)

Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued.^[2]^[3]^[4] It is still available for use in France however.^[3]^[4] It is taken by mouth.^[3]

Side effects of norethandrolone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.^[3] It can also cause estrogenic effects like fluid retention, breast tenderness, and breast enlargement in men and liver damage.^[3] 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).^[3]^[5] It has strong anabolic effects relative to its androgenic effects.^[3] The drug also has strong progestogenic effects.^[3]

Norethandrolone was discovered in 1953 and was introduced for medical use in 1956.^[6]^[7] It was the first AAS with a favorable separation of anabolic and androgenic effect to be marketed.^[7]^[8] The drug was mostly withdrawn in the 1980s due to concerns of liver damage.^[9] In addition to its medical use, norethandrolone has been used to improve physique and performance.^[3] The drug is a controlled substance in many countries and so non-medical use is generally illicit.^[3]

^ 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.
^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 885–. ISBN 978-1-4757-2085-3.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 575–583. ISBN 978-0-9828280-1-4.
^ ^a ^b "List of Androgens and anabolic steroids".
^ Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
^ Cite error: The named reference Kochakian2012 was invoked but never defined (see the help page).
^ ^a ^b Camille Georges Wermuth (2 May 2011). The Practice of Medicinal Chemistry. Academic Press. pp. 34–. ISBN 978-0-08-056877-5.
^ James Edward Wright (1994). Altered States: The Use and Abuse of Anabolic Steroids. Masters Press. p. 33. ISBN 978-1-57028-013-9.
^ Cite error: The named reference Sneader2005 was invoked but never defined (see the help page).

[1] 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.

[Elks2014-2] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 885–. ISBN 978-1-4757-2085-3.

[Llewellyn2011-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 575–583. ISBN 978-0-9828280-1-4.

[Drugs.com-4] "List of Androgens and anabolic steroids".

[pmid18500378-5] Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.

[Kochakian2012-6] Cite error: The named reference Kochakian2012 was invoked but never defined (see the help page).

[Wermuth2011-7] Camille Georges Wermuth (2 May 2011). The Practice of Medicinal Chemistry. Academic Press. pp. 34–. ISBN 978-0-08-056877-5.

[Wright1994-8] James Edward Wright (1994). Altered States: The Use and Abuse of Anabolic Steroids. Masters Press. p. 33. ISBN 978-1-57028-013-9.

[Sneader2005-9] Cite error: The named reference Sneader2005 was invoked but never defined (see the help page).

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