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]

Medical uses

Ethylestrenol has been used for a variety of indications including:[2]

Contraindications

Ethylestrenol should not be taken by pregnant women as it can masculinize female fetuses.[9] It is contraindicated in men with prostate cancer as it may accelerate the progression of the disease.[7]

Side effects

See also: Anabolic steroid § Adverse effects

Side effects of ethylestrenol include virilization among others.[2]

Pharmacology

Pharmacodynamics

Norethandrolone (3-ketoethylestrenol), the active metabolite of ethylestrenol.
Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
Medication Ratioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

As an AAS, ethylestrenol is an agonist of the androgen receptor (AR), similarly to androgens like testosterone and dihydrotestosterone (DHT).[2][4] It has low estrogenic activity (via aromatization into ethylestradiol following transformation into norethandrolone), strong progestogenic activity, and a high ratio of anabolic to androgenic activity, similarly to other nandrolone derivatives.[2] Like other 17α-alkylated AAS, ethylestrenol has a risk of hepatotoxicity.[2]

Relative affinities of nandrolone and related steroids at the androgen receptor
Compound rAR (%) hAR (%)
Testosterone 38 38
5α-Dihydrotestosterone 77 100
Nandrolone 75 92
5α-Dihydronandrolone 35 50
Ethylestrenol ND 2
Norethandrolone ND 22
5α-Dihydronorethandrolone ND 14
Metribolone 100 110
Sources: See template.

Pharmacokinetics

Ethylestrenol has very low affinity for human serum sex hormone-binding globulin (SHBG), less than 5% of that of testosterone and less than 1% of that of DHT.[10] It is known to be metabolized into the closely related AAS norethandrolone (17α-ethyl-19-nortestosterone) in the body and has been regarded as a prodrug of norethandrolone.[2] This is in accordance with its very low affinity for the androgen receptor, only about 5% of that of testosterone and 2% of that of dihydrotestosterone.[11]

Chemistry

See also: List of androgens/anabolic steroids

Ethylestrenol, also known as 3-deketo-17α-ethyl-19-nortestosterone or as 17α-ethylestr-4-en-17β-ol, is a synthetic estrane steroid and a 17α-alkylated derivative of nandrolone (19-nortestosterone; 19-NT).[5][12][2] It is specifically the 17α-ethyl and 3-deketo derivative of nandrolone as well as the 3-deketo derivative of norethandrolone (17α-ethyl-19-NT).[5][12][2] Other related AAS include bolenol (3-deketo-17α-ethyl-19-nor-5-androstenediol), ethyldienolone (17α-ethyl-δ9-19-NT), norboletone (17α-ethyl-18-methyl-19-NT), propetandrol (17α-ethyl-19-NT 3β-propionate), and tetrahydrogestrinone (THG; 17α-ethyl-18-methyl-δ9,11-19-NT). The progestins allylestrenol (3-deketo-17α-allyl-19-NT) and lynestrenol (3-deketo-17α-ethynyl-19-NT) are also closely related to ethylestrenol, differing only by the C17α substitution.

History

Ethylestrenol was described in the literature in 1959 and approved for medical use in 1961 and in the United States in 1964.[5][2][6]

Society and culture

Generic names

Ethylestrenol is the generic name of the drug and its INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, and BANTooltip British Approved Name, while éthylestrénol is its DCFTooltip Dénomination Commune Française and ethylnandrol is its JANTooltip Japanese Accepted Name.[5][12][13][3] The BANTooltip British Approved Name was formerly ethyloestrenol, but it was eventually changed.[5][12][13][3]

Brand names

Ethylestrenol is or has been marketed under a variety of brand names including Durabolin O, Duraboral, Fertabolin, Maxibolin, Maxibolin Elixir, Orabolin, Orgabolin, Orgaboral, and Virastine.[5][12][2] The brand name Durabolin O is a contraction of "Durabolin Oral", Durabolin being a brand name of the nandrolone ester nandrolone phenylpropionate.[2] Ethylestrenol is or has also been marketed for veterinary use under the brand names Nandoral, Nitrotain, and Oestrotain.[3][2]

Availability

The availability of ethylestrenol is very limited.[2][12][3] It appears to be available only in Australia and New Zealand and in these countries only for veterinary use.[2][3]

Ethylestrenol, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[14]

References

  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 m n o p q r s t u v w x y z William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 591–598. ISBN 978-0-9828280-1-4.
  3. ^ a b c d e f "Ethylestrenol". Drugs.com. Archived from the original on 2017-11-11. Retrieved 2017-11-10.
  4. ^ 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.
  5. ^ a b c d e f g Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 518–519. ISBN 978-1-4757-2085-3.
  6. ^ a b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 1513–1514. ISBN 978-0-8155-1856-3.
  7. ^ a b c d Ebadi M (31 October 2007). "Ethylestrenol". Desk Reference of Clinical Pharmacology (Second ed.). CRC Press. pp. 257–. ISBN 978-1-4200-4744-8.
  8. ^ a b c d Colby HD, Longhurst PA (6 December 2012). "Fate of Anabolic Steroids in the Body". In Thomas JA (ed.). Drugs, Athletes, and Physical Performance. Springer Science & Business Media. pp. 21–22. ISBN 978-1-4684-5499-4.
  9. ^ a b Miller RL (2002). The Encyclopedia of Addictive Drugs. Greenwood Publishing Group. pp. 156–. ISBN 978-0-313-31807-8.
  10. ^ Saartok T, Dahlberg E, Gustafsson JA (June 1984). "Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin". Endocrinology. 114 (6): 2100–2106. doi:10.1210/endo-114-6-2100. PMID 6539197.
  11. ^ Bergink EW, Geelen JA, Turpijn EW (1985). "Metabolism and receptor binding of nandrolone and testosterone under in vitro and in vivo conditions". Acta Endocrinologica. Supplementum. 271 (3_Suppla): 31–37. doi:10.1530/acta.0.109S0031. PMID 3865479.
  12. ^ a b c d e f Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 415–. ISBN 978-3-88763-075-1.
  13. ^ a b Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 116–. ISBN 978-94-011-4439-1.
  14. ^ Bono JP (21 December 2006). "Criminalistics: Introduction to Controlled Substances". In Karch SB (ed.). Drug Abuse Handbook (Second ed.). CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.