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11β-Methyl-19-nortestosterone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
11β-Methyl-19-nortestosterone
Clinical data
Other names11β-MNT; 11β-Methylestr-4-en-17β-ol-3-one
Routes of
administration
By mouth
Drug classAndrogen;Anabolic steroid;Progestogen
Identifiers
  • (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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H28O2
Molar mass288.431 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 asynthetic andorally activeanabolic–androgenic steroid (AAS) and aderivative ofnandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of theNational Institute of Child Health and Human Development (NICHD) and has not been marketed at this time.[1][2][3]

The C17βdodecylcarbonateester of 11β-MNT,11β-methyl-19-nortestosterone 17β-dodecylcarbonate (11β-MNTDC) (CDB-4754), is aprodrug of 11β-MNT.[1][2][3] Along with the closely related AASdimethandrolone (7α,11β-dimethyl-19-nortestosterone; CDB-1321) and its ester prodrugdimethandrolone undecanoate (CDB-4521), 11β-MNT and 11β-MNTDC are under investigation as potentialmale contraceptives and to treat malehypogonadism.[1][2][3]

Side effects

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See also:Anabolic steroid § Adverse effects

Pharmacology

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Pharmacodynamics

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11β-MNT does not undergoaromatization into the correspondingestrogenicmetabolite 11β-methylestradiol, and for this reason, has no potential for estrogenicside effects such asgynecomastia.[2] In addition, unliketestosterone, 11β-MNT does not appear to undergo5α-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 aspotent as 11β-MNT in terms ofandrogenicity inanimalbioassays, yet the co-administration of the5α-reductase inhibitordutasteride with 11β-MNT had no influence on its potency in assays using tissues that express 5α-reductase like theventral prostate andseminal vesicles.[3] Due to lack of potentiation by 5α-reductase in androgenic tissues like theskin,hair follicles, and prostate gland, 11β-MNT may have a lower risk of certain side effects such asoily skin,acne,androgenic alopecia (pattern hair loss),prostate enlargement, andprostate cancer than testosterone and certain other AAS.[3]

Similarly to nandrolone, dimethandrolone, and other 19-nortestosterone derivatives, 11β-MNT has been found to possessprogestogenic activity.[4] Because of its dual activity as an AAS and progestogen, 11β-MNT may have greaterefficacy in suppression ofspermatogenesis and hencemale fertility than pure AAS like testosterone.[4]

Oral 11β-MNT has shown little to no potential forhepatotoxicity in animals, similarly to testosterone but unlike17α-alkylated AAS likemethyltestosterone.[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 C7αmethyl group (although a risk that is still significantly lower than that of 17α-alkylated AAS).[5]

Chemistry

[edit]
See also:List of androgens/anabolic steroids

11β-MNT, or 11β-methyl-19-nortestosterone, also known as 11β-methylestr-4-en-17β-ol-3-one, is asyntheticestranesteroid and a non-17α-alkylatedderivative ofnandrolone (19-nortestosterone).[4]

References

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  1. ^abcAttardi 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.
  2. ^abcdAttardi 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.
  3. ^abcdefAttardi 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.
  4. ^abcAttardi 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.
  5. ^abHild 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.


ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
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