Chemical compound
Ethylestrenol
Trade names Maxibolin, Orabolin, others Other names Ethyloestrenol; 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.com
International Drug Names
Routes of administration
By mouth
Drug class
Androgen ;
Anabolic steroid ;
Progestogen
ATC code
Legal status
(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 InfoCard
100.012.294
Formula C 20 H 32 O
Molar mass 288.475 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
Y Key:AOXRBFRFYPMWLR-XGXHKTLJSA-N
Y
N Y
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(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
Side effects of ethylestrenol include
virilization among others.
[2]
Pharmacology
Pharmacodynamics
Norethandrolone (3-ketoethylestrenol), the
active metabolite of ethylestrenol.
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]
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
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
INN Tooltip International Nonproprietary Name ,
USAN Tooltip United States Adopted Name , and
BAN Tooltip British Approved Name , while éthylestrénol is its
DCF Tooltip Dénomination Commune Française and ethylnandrol is its
JAN Tooltip Japanese Accepted Name .
[5]
[12]
[13]
[3] The
BAN Tooltip 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]
Legal status
Ethylestrenol, along with other AAS, is a
schedule III
controlled substance in the
United States under the
Controlled Substances Act .
[14]
References
^
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 .
^
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 .
^
a
b
c
d
e
f
"Ethylestrenol" . Drugs.com . Archived from
the original on 2017-11-11. Retrieved 2017-11-10 .
^
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 .
^
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 .
^
a
b William Andrew Publishing (22 October 2013).
Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 1513–1514.
ISBN
978-0-8155-1856-3 .
^
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 .
^
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 .
^
a
b Miller RL (2002).
The Encyclopedia of Addictive Drugs . Greenwood Publishing Group. pp. 156–.
ISBN
978-0-313-31807-8 .
^ 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 .
^ 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 .
^
a
b
c
d
e
f
Index Nominum 2000: International Drug Directory . Taylor & Francis. 2000. pp. 415–.
ISBN
978-3-88763-075-1 .
^
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 .
^ 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 .
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