Dimethandrolone

Dimethandrolone
Clinical data
Routes of
administration		 Oral
Identifiers
Synonyms CDB-1321; 7α,11β-Dimethyl-19-nortestosterone
CAS Number
366472-45-9 (undecanoate)
PubChem (CID) 9882863
ChemSpider 8058538
Chemical and physical data
Formula C20H30O2
Molar mass 302.451 g/mol
3D model (Jmol) Interactive image

Dimethandrolone (DMA) (developmental code name CDB-1321), also known as 7α,11β-dimethyl-19-nortestosterone, is a potent, synthetic, orally active androgenic-anabolic steroid (AAS) or selective androgen receptor modulator (SARM) and progestogen of the 19-nortestosterone group related to nandrolone that was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development.[1][2][3] The 17β-undecanoate ester of dimethandrolone, dimethandrolone undecanoate (DMAU) (CDB-4521), is a prodrug of dimethandrolone that is cleaved by esterases and is under investigation as a method of androgen replacement therapy and as a potential male contraceptive.[1][2][3] A number of other esters, such as dimethandrolone buciclate (CDB-4386A) and dimethandrolone dodecylcarbonate (CDB-4730), have also been developed.[4][5]

Unlike testosterone and various other AAS, dimethandrolone is not metabolized by 5α-reductase.[2] In addition, the 5α-reduced derivative of dimethandrolone, 5α-dihydrodimethandrolone (5α-DHDMA), possesses only 30 to 40% of the potency of dimethandrolone as an agonist of the androgen receptor, indicating that dimethandrolone does not require potentiation by 5α-reductase for its activity as an AAS and that even if it were a substrate for 5α-reductase, it would not be potentiated in androgenic tissues like the skin and prostate.[2] As such, dimethandrolone and ester prodrugs of it like DMAU are thought to have a reduced risk of androgenic side effects and conditions such as benign prostate hyperplasia, prostate cancer, androgenetic alopecia, and acne relative to testosterone and certain other AAS.[2]

Dimethandrolone is not a substrate for aromatase, and for this reason, is not converted into the corresponding aromatic A-ring derivative 7α,11β-dimethylestradiol, a potent estrogen.[3][6] As such, dimethandrolone is not estrogenic.[6] This is in contrast to nandrolone, which, although its rate of aromatization into the estrogen estradiol is reduced relative to that of testosterone, is still converted to a significant extent.[6]

Similarly to nandrolone and other 19-nortestosterone derivatives, dimethandrolone is a potent progestogen in addition to AAS.[1] This property may serve to augment its antigonadotropic activity, which in turn may improve its effectiveness as an antispermatogenic agent and male contraceptive.[1] This is salient and potentially beneficial as male contraceptives based on androgens alone have failed to produce satisfactory azoospermia in around one-third of men.[1]

Dimethandrolone has shown minimal potential for hepatotoxicity in animal studies, which is in accordance with the fact that it is not a 17α-alkylated AAS.[7]

Other drugs that are closely related to dimethandrolone (besides nandrolone) include trestolone (also known as 7α-methyl-19-nortestosterone (MENT)) and 11β-methyl-19-nortestosterone (11β-MNT) and their respective C17β esters trestolone acetate and 11β-MNT dodecylcarbonate (11β-MNTDC).[1][2]

See also

References

  1. 1 2 3 4 5 6 Attardi, Barbara J.; Hild, Sheri A.; Reel, Jerry R. (June 2006). "Dimethandrolone Undecanoate: A New Potent Orally Active Androgen with Progestational Activity". Endocrinology. 147 (6): 3016–3026. doi:10.1210/en.2005-1524. ISSN 0013-7227. PMID 16497801.
  2. 1 2 3 4 5 6 Attardi, Barbara J.; Hild, Sheri A.; Koduri, Sailaja; Pham, Trung; Pessaint, Laurent; Engbring, Jean; Till, Bruce; Gropp, David; Semon, Anne; Reel, Jerry R. (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): 212–218. doi:10.1016/j.jsbmb.2010.06.009. PMC 2949447Freely accessible. PMID 20599615.
  3. 1 2 3 Wang, Christina; Swerdloff, Ronald S. (November 2010). "Hormonal Approaches to Male contraception". Current opinion in urology. 20 (6): 520–524. doi:10.1097/MOU.0b013e32833f1b4a. ISSN 0963-0643. PMC 3078035Freely accessible. PMID 20808223.
  4. ↑ Blye, Richard, and Hyun Kim. "Methods of making and using 7a, 11b-dimethyl-17b-hydroxy-4-estren-3-one 17b-trans-4-n-butylcyclohexane carboxylate and 7a, 11b-dimethyl-17b-hydroxyestr-4-en-3-one 17-undecanoate." U.S. Patent Application No. 10/260,854.
  5. ↑ Blye, Richard P., and Hyun K. Kim. "Nandrolone 17β-carbonates." U.S. Patent No. 7,820,642. 26 Oct. 2010.
  6. 1 2 3 Attardi, Barbara J.; Pham, Trung C.; Radler, Lisa M.; Burgenson, Janet; Hild, Sheri A.; Reel, Jerry R. (June 2008). "Dimethandrolone (7α,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): 214–222. doi:10.1016/j.jsbmb.2007.11.009. PMC 2575079Freely accessible. PMID 18555683.
  7. ↑ Attardi, Barbara J.; Engbring, Jean A.; Gropp, David; Hild, Sheri Ann (September–October 2011). "Development of Dimethandrolone 17β-Undecanoate (DMAU) as an Oral Male Hormonal Contraceptive: Induction of Infertility and Recovery of Fertility in Adult Male Rabbits". Journal of Andrology. 32 (5): 530–540. doi:10.2164/jandrol.110.011817. ISSN 1939-4640. PMID 21164142.


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