Chemical compound
Norethandrolone
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
Legal status
(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
PubChem
CID
ChemSpider
UNII
KEGG
CompTox Dashboard (
EPA )
ECHA InfoCard
100.000.140
Formula C 20 H 30 O 2
Molar mass 302.458 g·mol−1 3D model (
JSmol )
O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)CC)[C@@H]2CC3)C)CC4
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
Y Key:ZDHCJEIGTNNEMY-XGXHKTLJSA-N
Y
(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[8] The drug was mostly withdrawn in the 1980s due to concerns of liver damage.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]
Medical uses
Norethandrolone has been used in the treatment of
muscle wasting ,
[9] patients with severe
burns , after severe
trauma , and for certain forms of
aplastic anemia among other indications.
[3]
Side effects
Side effects of norethandrolone include
virilization among others.
[3] It has
estrogenic effects and can cause
gynecomastia and
fluid retention .
[3] As with all
17α-alkylated AAS , long-term use of norethandrolone in high doses may result in
hepatotoxicity including
elevated liver enzymes and
cirrhosis .
[10]
Pharmacology
Pharmacodynamics
Norethandrolone is an
androgen and
anabolic steroid and hence is an
agonist of the
androgen receptor , the
biological target of androgens like
testosterone and
dihydrotestosterone .
[3] It has a high ratio of
anabolic to
androgenic activity.
[3] Analogously to the case of
nandrolone and
5α-dihydronandrolone ,
5α-dihydronorethandrolone , the
5α-reduced
metabolite of norethandrolone, shows diminished
affinity for the androgen receptor relative to norethandrolone.
[3]
[11] This is likely related to the high ratio of anabolic to androgenic activity observed with norethandrolone.
[3]
[11] Norethandrolone has relatively high
estrogenic activity via transformation by
aromatase into the potent
estrogen
ethylestradiol .
[3] It also has strong
progestogenic activity.
[3] The progestogenic
potency of norethandrolone is similar to that of
norethisterone in terms of
endometrial changes in women.
[12] In addition, norethandrolone is
hepatotoxic .
[3]
Pharmacokinetics
The
pharmacokinetics of norethandrolone have been reviewed.
[13]
Chemistry
Norethandrolone, also known as 17α-ethyl-19-nortestosterone or as 17α-ethylestr-4-en-17β-ol-3-one, is a
synthetic
estrane
steroid and a
17α-alkylated
derivative of
testosterone and
19-nortestosterone (nandrolone).
[2]
[3] It is closely related to
normethandrone (17α-methyl-19-nortestosterone) and to
ethylestrenol (3-deketo-17α-ethyl-19-nortestosterone).
[2]
[3]
Synthesis
Chemical syntheses of norethandrolone have been published.
[13]
History
Norethandrolone was synthesized at
G. D. Searle & Company in 1953 and was originally studied as a
progestin , along with
norethisterone and
noretynodrel , but ultimately was not marketed as such.
[6] In 1955, it was re-examined for
testosterone -like activity and was found to have similar
anabolic activity to testosterone but only one-sixteenth the
androgenic potency.
[6]
[9] Norethandrolone was introduced for medical use as an AAS in 1956 and was the first so-called "anabolic steroid", or AAS with a favorable separation of anabolic and androgenic effect, to be marketed.
[7]
[8] It was followed by
normethandrone as a progestin in 1957 and by the more well-known AAS
nandrolone phenylpropionate in 1959.
[14]
[8] Norethandrolone was introduced in the
United States in the late 1950s under the brand name Nilevar but was discontinued in this country in the 1960s due to limited sales.
[3] Although it was also introduced into
Europe and certain other markets,
[3] it was withdrawn in many countries in the 1980s due to concerns of
cholestatic jaundice .
[9] Today, the drug remains available only in
France .
[3]
[4]
Society and culture
Generic names
Norethandrolone is the
generic name of the drug and its
INN Tooltip International Nonproprietary Name and
BAN Tooltip British Approved Name .
[2]
[4] It has also been referred to as noretandrolone , ethylnandrolone , and ethylnortestosterone , as well as by its developmental code name CB-8022 .
[2]
[4]
Brand names
Norethandrolone is marketed under the brand names Nilevar and Pronabol.
[2]
[3]
[4]
Availability
Norethandrolone is available today only in
France .
[4]
[15]
Research
Norethandrolone has been studied for use in
male hormonal contraception .
[16]
[17]
[18]
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 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
k
l
m
n
o
p
q
r
s
t
u
v
w
x
y
z William Llewellyn (2011).
Anabolics . Molecular Nutrition Llc. pp. 575–583.
ISBN
978-0-9828280-1-4 .
^
a
b
c
d
e
f
g
"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 .
^
a
b
c Charles D. Kochakian (6 December 2012).
Anabolic-Androgenic Steroids . Springer Science & Business Media. pp. 380–.
ISBN
978-3-642-66353-6 .
^
a
b
c Camille Georges Wermuth (2 May 2011).
The Practice of Medicinal Chemistry . Academic Press. pp. 34–.
ISBN
978-0-08-056877-5 .
^
a
b
c James Edward Wright (1994).
Altered States: The Use and Abuse of Anabolic Steroids . Masters Press. p. 33.
ISBN
978-1-57028-013-9 .
^
a
b
c
d Walter Sneader (23 June 2005).
Drug Discovery: A History . John Wiley & Sons. pp. 206–.
ISBN
978-0-471-89979-2 .
^ Daniel Lednicer (20 June 2011).
Steroid Chemistry at a Glance . John Wiley & Sons. pp. 67–.
ISBN
978-1-119-95729-4 .
^
a
b Bergink EW, Geelen JA, Turpijn EW (1985). "Metabolism and receptor binding of nandrolone and testosterone under in vitro and in vivo conditions". Acta Endocrinol Suppl (Copenh) . 271 (3_Suppla): 31–7.
doi :
10.1530/acta.0.109S0031 .
PMID
3865479 .
^ Boschann HW (July 1958). "Observations of the role of progestational agents in human gynecologic disorders and pregnancy complications". Ann. N. Y. Acad. Sci . 71 (5): 727–52.
Bibcode :
1958NYASA..71..727B .
doi :
10.1111/j.1749-6632.1958.tb46803.x .
PMID
13583829 .
^
a
b
Die Gestagene . Springer-Verlag. 27 November 2013. pp. 13, 282–283.
ISBN
978-3-642-99941-3 .
^ United States. Patent Office (1957).
Official Gazette of the United States Patent Office . U.S. Patent Office.
^
"IBM Watson Health Products" .
^ Schearer SB, Alvarez-Sanchez F, Anselmo J, Brenner P, Coutinho E, Latham-Faundes A, et al. (1978).
"Hormonal Contraception for Men" . International Journal of Andrology . 1 (s2b): 680–712.
doi :
10.1111/j.1365-2605.1978.tb00517.x .
ISSN
0105-6263 .
^ Neumann F, Diallo FA, Hasan SH, Schenck B, Traore I (1976).
"The influence of pharmaceutical compounds on male fertility" . Andrologia . 8 (3): 203–35.
doi :
10.1111/j.1439-0272.1976.tb02137.x .
PMID
793446 .
S2CID
24859886 .
^ Brenner PF, Bernstein GS, Roy S, Jecht EW, Mishell DR (February 1975). "Administration of norethandrolone and testosterone as a contraceptive agent for men". Contraception . 11 (2): 193–207.
doi :
10.1016/0010-7824(75)90030-x .
PMID
1112088 .
Androgens (incl.
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Steroidal:
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Abiraterone
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RU-16117
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RU-2309
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