Ethylestrenol

Ethylestrenol
Clinical data
Trade namesMaxibolin, Orabolin, others
Other namesEthyloestrenol; Ethylnandrol; ORG-483; 3-Deketo-17α-ethyl-19-nortestosterone; 17α-Ethylestr-4-en-17β-ol; 19-Nor-17α-pregn-4-en-17β-ol
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
Drug classAndrogen; Anabolic steroid; Progestogen
ATC code
Legal status
Legal status
Identifiers
  • (8R,9S,10R,13S,14S,17S)-17-ethyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.012.294 Edit this at Wikidata
Chemical and physical data
FormulaC20H32O
Molar mass288.475 g·mol−1
3D model (JSmol)
  • O[C@]2(CC[C@H]1[C@H]4[C@H](CC[C@@]12C)[C@@H]3\C(=C/CCC3)CC4)CC
  • InChI=1S/C20H32O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h6,15-18,21H,3-5,7-13H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1 checkY
  • Key:AOXRBFRFYPMWLR-XGXHKTLJSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such as to promote weight gain and to treat anemia and osteoporosis but has been discontinued for use in humans.[2] It is still available for veterinary use in Australia and New Zealand however.[3] It is taken by mouth.[2]

Side effects of ethylestrenol include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[2] It can also cause liver damage.[2] 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).[2][4] It has strong anabolic effects relative to its androgenic effects.[2] The drug also has strong progestogenic effects.[2] Ethylestrenol is a prodrug of norethandrolone.[2]

Ethylestrenol was first described in 1959 and was introduced for medical use in 1961.[5][2][6] In addition to its medical use, ethylestrenol has been used to improve physique and performance.[2] However, it is described as a very weak muscle-builder compared to other AAS and in relation to this has not been commonly used for such purposes.[2] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[2]

  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.
  2. ^ a b c d e f g h i j k l William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 591–598. ISBN 978-0-9828280-1-4.
  3. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference Kicman2008 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).