From Wikipedia, the free encyclopedia
Chemical compound
11β-Methyl-19-nortestosterone
Other names 11β-MNT; 11β-Methylestr-4-en-17β-ol-3-one
Routes of administration
By mouth
Drug class
Androgen ;
Anabolic steroid ;
Progestogen
(8R ,9S ,10R ,11S ,13S ,14S ,17S )-17-hydroxy-11,13-dimethyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H -cyclopenta[a ]phenanthren-3-one
CAS Number
PubChem
CID
ChemSpider
UNII
Formula C 19 H 28 O 2
Molar mass 288.431 g·mol−1 3D model (
JSmol )
C[C@H]1C[C@]2(C)[C@@H](O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@@H]13
InChI=1S/C19H28O2/c1-11-10-19(2)16(7-8-17(19)21)15-5-3-12-9-13(20)4-6-14(12)18(11)15/h9,11,14-18,21H,3-8,10H2,1-2H3/t11-,14-,15-,16-,17-,18+,19-/m0/s1
Key:QCNNHARIRLYUAB-CTPXPINYSA-N
11β-Methyl-19-nortestosterone (11β-MNT ) is a
synthetic and
orally active
anabolic–androgenic steroid (AAS) and a
derivative of
nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the
National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time.
[1]
[2]
[3]
The C17β
dodecyl
carbonate
ester of 11β-MNT,
11β-methyl-19-nortestosterone 17β-dodecylcarbonate (11β-MNTDC) (CDB-4754), is a
prodrug of 11β-MNT.
[1]
[2]
[3] Along with the closely related AAS
dimethandrolone (7α,11β-dimethyl-19-nortestosterone; CDB-1321) and its ester prodrug
dimethandrolone undecanoate (CDB-4521), 11β-MNT and 11β-MNTDC are under investigation as potential
male contraceptives and to treat male
hypogonadism .
[1]
[2]
[3]
Side effects
Pharmacology
Pharmacodynamics
11β-MNT does not undergo
aromatization into the corresponding
estrogenic
metabolite 11β-methylestradiol, and for this reason, has no potential for estrogenic
side effects such as
gynecomastia .
[2] In addition, unlike
testosterone , 11β-MNT does not appear to undergo
5α-reduction into the corresponding 5α-
dihydrogenated metabolite 5α-dihydro-11β-MNT (5α-DHMNT).
[3] This conclusion is based on the fact that 5α-DHMNT is 4 to 8 times as
potent as 11β-MNT in terms of
androgenicity in
animal
bioassays , yet the co-administration of the
5α-reductase inhibitor
dutasteride with 11β-MNT had no influence on its potency in assays using tissues that express 5α-reductase like the
ventral prostate and
seminal vesicles .
[3] Due to lack of potentiation by 5α-reductase in androgenic tissues like the
skin ,
hair follicles , and prostate gland, 11β-MNT may have a lower risk of certain side effects such as
oily skin ,
acne ,
androgenic alopecia (pattern hair loss),
prostate enlargement , and
prostate cancer than testosterone and certain other AAS.
[3]
Similarly to nandrolone, dimethandrolone, and other 19-nortestosterone derivatives, 11β-MNT has been found to possess
progestogenic activity.
[4] Because of its dual activity as an AAS and progestogen, 11β-MNT may have greater
efficacy in suppression of
spermatogenesis and hence
male fertility than pure AAS like testosterone.
[4]
Oral 11β-MNT has shown little to no potential for
hepatotoxicity in animals, similarly to testosterone but unlike
17α-alkylated AAS like
methyltestosterone .
[5] The drug notably shows a much lower hepatotoxic potential than dimethandrolone and trestolone (7α-methyl-19-nortestosterone; MENT), which may have an increased risk due to their shared C7α
methyl group (although a risk that is still significantly lower than that of 17α-alkylated AAS).
[5]
Chemistry
11β-MNT, or 11β-methyl-19-nortestosterone, also known as 11β-methylestr-4-en-17β-ol-3-one, is a
synthetic
estrane
steroid and a non-17α-alkylated
derivative of
nandrolone (19-nortestosterone).
[4]
References
^
a
b
c Attardi BJ, Marck BT, Matsumoto AM, Koduri S, Hild SA (2011).
"Long-term effects of dimethandrolone 17β-undecanoate and 11β-methyl-19-nortestosterone 17β-dodecylcarbonate on body composition, bone mineral density, serum gonadotropins, and androgenic/anabolic activity in castrated male rats" . J. Androl . 32 (2): 183–92.
doi :
10.2164/jandrol.110.010371 .
PMID
20798389 .
^
a
b
c
d Attardi BJ, Pham TC, Radler LC, Burgenson J, Hild SA, Reel JR (2008).
"Dimethandrolone (7alpha,11beta-dimethyl-19-nortestosterone) and 11beta-methyl-19-nortestosterone are not converted to aromatic A-ring products in the presence of recombinant human aromatase" . J. Steroid Biochem. Mol. Biol . 110 (3–5): 214–22.
doi :
10.1016/j.jsbmb.2007.11.009 .
PMC
2575079 .
PMID
18555683 .
^
a
b
c
d
e
f Attardi BJ, Hild SA, Koduri S, Pham T, Pessaint L, Engbring J, Till B, Gropp D, Semon A, Reel JR (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" . J. Steroid Biochem. Mol. Biol . 122 (4): 212–8.
doi :
10.1016/j.jsbmb.2010.06.009 .
PMC
2949447 .
PMID
20599615 .
^
a
b
c Attardi BJ, Hild SA, Reel JR (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 .
^
a
b Hild SA, Attardi BJ, Koduri S, Till BA, Reel JR (2010).
"Effects of synthetic androgens on liver function using the rabbit as a model" . J. Androl . 31 (5): 472–81.
doi :
10.2164/jandrol.109.009365 .
PMC
2943539 .
PMID
20378929 .
AR Tooltip Androgen receptor
Agonists
SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A
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 )