Chemical compound
Trestolone
Other names MENT; MENTR; RU-27333; 7α-Methylnandrolone; 7α-Methyl-19-nortestosterone; 7α-Methylestr-4-en-17β-ol-3-one
Routes of administration
Subcutaneous implant ,
intramuscular injection (as
trestolone acetate )
Drug class
Androgen ;
Anabolic steroid ;
Progestogen ;
Antigonadotropin
ATC code
(7R ,8R ,9S ,10R ,13S ,14S ,17S )-17-hydroxy-7,13-dimethyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H -cyclopenta[a ]phenanthren-3-one
CAS Number
PubChem
CID
DrugBank
ChemSpider
UNII
CompTox Dashboard (
EPA )
ECHA InfoCard
100.184.887
Formula C 19 H 28 O 2
Molar mass 288.431 g·mol−1 3D model (
JSmol )
O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1[C@H](C)C2)C)CC4
InChI=1S/C19H28O2/c1-11-9-12-10-13(20)3-4-14(12)15-7-8-19(2)16(18(11)15)5-6-17(19)21/h10-11,14-18,21H,3-9H2,1-2H3/t11-,14+,15-,16+,17+,18-,19+/m1/s1
N Key:YSGQGNQWBLYHPE-CFUSNLFHSA-N
N
(verify)
Trestolone , also known as 7α-methyl-19-nortestosterone (MENT ), is an
experimental
androgen /
anabolic steroid (AAS) and
progestogen medication which has been under development for potential use as a form of
hormonal birth control for men and in
androgen replacement therapy for
low testosterone levels in men but has never been marketed for medical use.
[1]
[2]
[3]
[4]
[5] It is given as an
implant that is placed into fat .
[3] As
trestolone acetate , an
androgen ester and
prodrug of trestolone, the medication can also be given by
injection into muscle .
[1]
[5]
Side effects of trestolone use in men include
low estrogen levels and associated
symptoms such as
reduced sexual function and
decreased bone mineral density among others.
[5]
[3]
[6] Trestolone is an AAS, and hence is an
agonist of the
androgen receptor , the
biological target of androgens like
testosterone .
[3]
[7] It is also a
progestin , or a
synthetic progestogen, and hence is an agonist of the
progesterone receptor , the biological target of progestogens like
progesterone .
[3]
[7] Due to its androgenic and progestogenic activity, trestolone has
antigonadotropic effects.
[3]
[7] These effects result in reversible suppression of
sperm production and are responsible for the
contraceptive effects of trestolone in men.
[3]
Trestolone was first described in 1963.
[8] Subsequently, it was not studied again until 1990.
[9] Development of trestolone for potential clinical use started by 1993 and continued thereafter.
[4]
[10] No additional development appears to have been conducted since 2013.
[3] The medication was developed by the
Population Council , a
non-profit ,
non-governmental organization dedicated to
reproductive health .
[3]
[11]
Medical uses
Trestolone is an experimental medication and is not currently approved for medical use.
[2]
[3] It has been under development for potential use as a
male hormonal contraceptive and in
androgen replacement therapy for
low testosterone levels .
[2]
[3]
[4]
[10]
[5] The medication has been studied and developed for use as a
subcutaneous implant .
[3] An
androgen ester and
prodrug of trestolone,
trestolone acetate , has also been developed, for use via
intramuscular injection .
[1]
[5]
Side effects
Trestolone may cause
sexual dysfunction (e.g.,
decreased sex drive ,
reduced erectile function ) and decreased
bone mineral density due to
estrogen deficiency .
[5]
[3]
[6]
Pharmacology
Pharmacodynamics
As an AAS, trestolone is an
agonist of the
androgen receptor (AR), similarly to
androgens like
testosterone and
dihydrotestosterone (DHT).
[4]
[3] Trestolone is not a
substrate for
5α-reductase and hence is not potentiated or inactivated in so-called "androgenic"
tissues like the
skin ,
hair follicles , and
prostate gland .
[12] As such, it has a high ratio of
anabolic to
androgenic activity, similarly to other nandrolone derivatives.
[4]
[3] Trestolone is a substrate for
aromatase and hence produces the
estrogen
7α-methylestradiol as a
metabolite .
[7]
[13] However, trestolone has only weak
estrogenic activity and an amount that would appear to be insufficient for replacement purposes, as evidenced by decreased
bone mineral density in men treated with it for hypogonadism.
[5]
[3] Trestolone also has
potent
progestogenic activity.
[7]
[3] Both the androgenic and progestogenic activity of trestolone are thought to be involved in its
antigonadotropic activity.
[7]
[3]
Relative affinities (%) of trestolone and related steroids
[14]
[15]
[16]
[17]
[18]
Compound
PR Tooltip Progesterone receptor
AR Tooltip Androgen receptor
ER Tooltip Estrogen receptor
GR Tooltip Glucocorticoid receptor
MR Tooltip Mineralocorticoid receptor
SHBG Tooltip Sex hormone-binding globulin
CBG Tooltip Corticosteroid binding globulin
Nandrolone
20
154–155
<0.1
0.5
1.6
1
?
Trestolone
50–75
100–125
?
<1
?
?
?
7α-Methylestradiol
1–3
15–25
101
<1
<1
?
?
Values are percentages (%). Reference
ligands (100%) were
progesterone for the
PR Tooltip progesterone receptor ,
testosterone for the
AR Tooltip androgen receptor ,
E2 for the
ER Tooltip estrogen receptor ,
DEXA Tooltip dexamethasone for the
GR Tooltip glucocorticoid receptor ,
aldosterone for the
MR Tooltip mineralocorticoid receptor ,
DHT Tooltip dihydrotestosterone for
SHBG Tooltip sex hormone-binding globulin , and
cortisol for
CBG Tooltip Corticosteroid-binding globulin .
Mechanism of action
Spermatozoa are produced in the
testes of males in a process called
spermatogenesis . In order to render a man infertile, a hormone-based male contraceptive method must stop spermatogenesis by interrupting the release of
gonadotropins from the
pituitary gland . Even in low concentrations, trestolone is a potent inhibitor of the release of the gonadotropins,
luteinizing hormone (LH) and
follicle stimulating hormone (FSH).
[4]
[3] In order for spermatogenesis to occur in the testes, both FSH and testosterone must be present. By inhibiting release of FSH, trestolone creates an endocrine environment in which conditions for spermatogenesis are not ideal.
[4]
[3] Manufacture of sperm is further impaired by the suppression of LH, which in turn drastically curtails the production of testosterone.
[4]
[3] Sufficient regular doses of trestolone cause severe
oligozoospermia or
azoospermia , and therefore infertility, in most men.
[4]
[3] Trestolone-induced infertility has been found to be quickly reversible upon discontinuation.
[4]
[3]
When LH release is inhibited, the amount of testosterone made in the testes declines dramatically.
[4]
[3] As a result of trestolone's gonadotropin-suppressing qualities, levels of serum testosterone fall sharply in men treated with sufficient amounts of the medication.
[4]
[3] Testosterone is the main hormone responsible for maintenance of male
secondary sex characteristics . Normally, an inadequate testosterone level causes undesirable effects such as
fatigue , loss of
skeletal muscle mass, reduced
libido , and weight gain. However, the androgenic and anabolic properties of trestolone largely ameliorate this problem
[4]
[3] — essentially, trestolone replaces testosterone's role as the primary male hormone in the body.
[4]
[3]
Pharmacokinetics
The
pharmacokinetic properties of trestolone, such as poor oral
bioavailability and short
elimination half-life , make it unsuitable for
oral administration or long-term
intramuscular injection .
[19]
[20] As such, trestolone must be administered
parenterally via a different and more practical route such as
subcutaneous implant ,
transdermal patch , or
topical gel .
[19]
Trestolone acetate , a
prodrug of trestolone, can be administered via
intramuscular injection .
[5]
Chemistry
Trestolone, also known as 7α-methyl-19-nortestosterone (MENT) or as 7α-methylestr-4-en-17β-ol-3-one, is a
synthetic
estrane
steroid and a
derivative of
nandrolone (19-nortestosterone).
[1] It is a modification of nandrolone with a
methyl group at the C7α position.
[1] Closely related AAS include
7α-methyl-19-norandrostenedione (MENT dione, trestione) (an
androgen prohormone of trestolone) and
dimethandrolone (7α,11β-dimethyl-19-nortestosterone) (the C11β methylated derivative of trestolone), as well as
mibolerone (7α,17α-dimethyl-19-nortestosterone) and
dimethyltrienolone (7α,17α-dimethyl-δ9,11 -19-nortestosterone).
[1] The
progestin
tibolone (7α-methyl-17α-ethynyl-δ5(10) -19-nortestosterone) is also closely related to trestolone.
[1]
History
Trestolone was first described in 1963.
[8] However, it was not subsequently studied again until 1990.
[9]
[21] Development of trestolone for potential use in
male hormonal contraception and
androgen replacement therapy was started by 1993, and continued thereafter.
[4]
[10]
[3] No additional development appears to have been conducted since 2013.
[3] Trestolone was developed by the
Population Council , a
non-profit ,
non-governmental organization dedicated to
reproductive health ..
[3]
[11]
Society and culture
Generic names
Trestolone is the
generic name of the drug and its
INN Tooltip International Nonproprietary Name .
[1] It is also commonly known as 7α-methyl-19-nortestosterone (MENT ).
[1]
[2]
[3]
References
^
a
b
c
d
e
f
g
h
i J. Elks (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 888–.
ISBN
978-1-4757-2085-3 .
^
a
b
c
d
"7-alpha-methyl-19-nortestosterone - AdisInsight" .
^
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c
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e
f
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h
i
j
k
l
m
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p
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aa
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ad
ae Nieschlag E, Kumar N, Sitruk-Ware R (2013). "7α-methyl-19-nortestosterone (MENTR): the population council's contribution to research on male contraception and treatment of hypogonadism". Contraception . 87 (3): 288–95.
doi :
10.1016/j.contraception.2012.08.036 .
PMID
23063338 .
^
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i
j
k
l
m
n
o Sundaram K, Kumar N, Bardin CW (April 1993). "7 alpha-methyl-nortestosterone (MENT): the optimal androgen for male contraception". Ann. Med . 25 (2): 199–205.
doi :
10.3109/07853899309164168 .
PMID
8489761 .
^
a
b
c
d
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g
h Corona G, Rastrelli G, Vignozzi L, Maggi M (2012). "Emerging medication for the treatment of male hypogonadism". Expert Opin Emerg Drugs . 17 (2): 239–59.
doi :
10.1517/14728214.2012.683411 .
PMID
22612692 .
S2CID
22068249 .
^
a
b Anderson RA, Wallace AM, Sattar N, Kumar N, Sundaram K (June 2003).
"Evidence for tissue selectivity of the synthetic androgen 7 alpha-methyl-19-nortestosterone in hypogonadal men" . J. Clin. Endocrinol. Metab . 88 (6): 2784–93.
doi :
10.1210/jc.2002-021960 .
PMID
12788888 .
^
a
b
c
d
e
f García-Becerra R, Ordaz-Rosado D, Noé G, Chávez B, Cooney AJ, Larrea F (2012).
"Comparison of 7α-methyl-19-nortestosterone effectiveness alone or combined with progestins on androgen receptor mediated-transactivation" . Reproduction . 143 (2): 211–9.
doi :
10.1530/REP-11-0171 .
PMID
22065861 .
^
a
b Lyster SC, Duncan GW (July 1963). "Anabolic, androgenic and myotropic activities of derivatives of 7alpha-methyl-19-nortestosterone". Acta Endocrinol . 43 (3): 399–411.
doi :
10.1530/acta.0.0430399 .
PMID
13931986 .
^
a
b Ma JB, Li ZS (1990). "[Synthesis of 4-substituted 17 beta-hydroxy-7 alpha-methyl-4-estren-3-one and their 17-acetates as antifertility compounds]". Yao Xue Xue Bao (in Chinese). 25 (1): 18–23.
PMID
2363352 .
^
a
b
c Sundaram K, Kumar N, Bardin CW (1994). "7 alpha-Methyl-19-nortestosterone: an ideal androgen for replacement therapy". Recent Prog. Horm. Res . 49 : 373–6.
doi :
10.1016/b978-0-12-571149-4.50027-1 .
ISBN
9780125711494 .
PMID
8146434 .
^
a
b
MENT – project information from the Population Council
^ Attardi BJ, Hild SA, Koduri S, Pham T, Pessaint L, Engbring J, Till B, Gropp D, Semon A, Reel JR (October 2010).
"The potent synthetic androgens, dimethandrolone (7α,11β-dimethyl-19-nortestosterone) and 11β-methyl-19-nortestosterone, do not require 5α-reduction to exert their maximal androgenic effects" . The Journal of Steroid Biochemistry and Molecular Biology . 122 (4): 212–8.
doi :
10.1016/j.jsbmb.2010.06.009 .
PMC
2949447 .
PMID
20599615 .
^ Attardi BJ, Pham TC, Radler LC, Burgenson J, Hild SA, Reel JR (June 2008).
"Dimethandrolone (7,11β-dimethyl-19-nortestosterone) and 11β-methyl-19-nortestosterone are not converted to aromatic A-ring products in the presence of recombinant human aromatase" . The Journal of Steroid Biochemistry and Molecular Biology . 110 (3–5): 214–22.
doi :
10.1016/j.jsbmb.2007.11.009 .
PMC
2575079 .
PMID
18555683 .
^ Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". J. Steroid Biochem . 27 (1–3): 255–69.
doi :
10.1016/0022-4731(87)90317-7 .
PMID
3695484 .
^ Delettré J, Mornon JP, Lepicard G, Ojasoo T, Raynaud JP (January 1980). "Steroid flexibility and receptor specificity". J. Steroid Biochem . 13 (1): 45–59.
doi :
10.1016/0022-4731(80)90112-0 .
PMID
7382482 .
^ Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, Labrie F, Mornon JP (January 1980). "Steroid hormone receptors and pharmacology". J. Steroid Biochem . 12 : 143–57.
doi :
10.1016/0022-4731(80)90264-2 .
PMID
7421203 .
^ Ojasoo T, Raynaud JP, Doé JC (January 1994). "Affiliations among steroid receptors as revealed by multivariate analysis of steroid binding data". J. Steroid Biochem. Mol. Biol . 48 (1): 31–46.
doi :
10.1016/0960-0760(94)90248-8 .
PMID
8136304 .
S2CID
21336380 .
^ Raynaud J, Ojasoo T, Bouton M, Philibert D (1979).
"Receptor Binding as a Tool in the Development of New Bioactive Steroids" .
Drug Design: Medicinal Chemistry: A Series of Monographs . Vol. 8. New York, Academic Press. pp.
169–214 .
doi :
10.1016/B978-0-12-060308-4.50010-X .
ISBN
9780120603084 .
^
a
b Attardi BJ, Hild SA, Reel JR (June 2006).
"Dimethandrolone undecanoate: a new potent orally active androgen with progestational activity" . Endocrinology . 147 (6): 3016–26.
doi :
10.1210/en.2005-1524 .
PMID
16497801 . The pharmacokinetic properties of MENT make it unsuitable for once-daily oral treatment or long-term injection; thus, administration by sc implant or by patch or gel is required (27). MENT showed a more rapid metabolic clearance rate than T in men and monkeys, probably due in part to its failure to bind SHBG (28). In monkeys, MENT acetate in subdermal implants was 10 times as potent as T in suppression of gonadotropin secretion and anabolic effects, but was only twice as potent in stimulating prostate growth (29).
^ Suvisaari J, Sundaram K, Noé G, Kumar N, Aguillaume C, Tsong YY, Lähteenmäki P, Bardin CW (May 1997).
"Pharmacokinetics and pharmacodynamics of 7alpha-methyl-19-nortestosterone after intramuscular administration in healthy men" . Hum. Reprod . 12 (5): 967–73.
doi :
10.1093/humrep/12.5.967 .
PMID
9194649 .
^ Kumar N, Didolkar AK, Ladd A, Thau R, Monder C, Bardin CW, Sundaram K (November 1990). "Radioimmunoassay of 7 alpha-methyl-19-nortestosterone and investigation of its pharmacokinetics in animals". J. Steroid Biochem. Mol. Biol . 37 (4): 587–91.
doi :
10.1016/0960-0760(90)90405-a .
PMID
2278844 .
S2CID
37597215 .
AR Tooltip Androgen receptor
Agonists
SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A
ER Tooltip Estrogen receptor
Agonists
Steroidal:
2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (
alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g.,
testosterone and
esters ,
methyltestosterone ,
metandienone (methandrostenolone) ,
nandrolone and
esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
ent -Estradiol
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
Xenoestrogens:
Anise -related (e.g.,
anethole ,
anol ,
dianethole ,
dianol ,
photoanethole )
Chalconoids (e.g.,
isoliquiritigenin ,
phloretin ,
phlorizin (phloridzin) ,
wedelolactone )
Coumestans (e.g.,
coumestrol ,
psoralidin )
Flavonoids (incl.
7,8-DHF ,
8-prenylnaringenin ,
apigenin ,
baicalein ,
baicalin ,
biochanin A ,
calycosin ,
catechin ,
daidzein ,
daidzin ,
ECG ,
EGCG ,
epicatechin ,
equol ,
formononetin ,
glabrene ,
glabridin ,
genistein ,
genistin ,
glycitein ,
kaempferol ,
liquiritigenin ,
mirificin ,
myricetin ,
naringenin ,
penduletin ,
pinocembrin ,
prunetin ,
puerarin ,
quercetin ,
tectoridin ,
tectorigenin )
Lavender oil
Lignans (e.g.,
enterodiol ,
enterolactone ,
nyasol (cis -hinokiresinol) )
Metalloestrogens (e.g.,
cadmium )
Pesticides (e.g.,
alternariol ,
dieldrin ,
endosulfan ,
fenarimol ,
HPTE ,
methiocarb ,
methoxychlor ,
triclocarban ,
triclosan )
Phytosteroids (e.g.,
digitoxin (
digitalis ),
diosgenin ,
guggulsterone )
Phytosterols (e.g.,
β-sitosterol ,
campesterol ,
stigmasterol )
Resorcylic acid lactones (e.g.,
zearalanone ,
α-zearalenol ,
β-zearalenol ,
zearalenone ,
zeranol (α-zearalanol) ,
taleranol (teranol, β-zearalanol) )
Steroid -like (e.g.,
deoxymiroestrol ,
miroestrol )
Stilbenoids (e.g.,
resveratrol ,
rhaponticin )
Synthetic xenoestrogens (e.g.,
alkylphenols ,
bisphenols (e.g.,
BPA ,
BPF ,
BPS ),
DDT ,
parabens ,
PBBs ,
PHBA ,
phthalates ,
PCBs )
Others (e.g.,
agnuside ,
rotundifuran )
Mixed (
SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators:
ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins:
6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g.,
levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g.,
norethisterone acetate ,
norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids:
11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g.,
nandrolone decanoate ,
nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g.,
trenbolone acetate ,
trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Mixed (
SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (
PAQR Tooltip Progestin and adipoQ receptor )