 | |
| Clinical data | |
|---|---|
| Other names | CDB-1321; Dimethylnandrolone; 7α,11β-Dimethyl-19-nortestosterone; 7α,11β-Dimethylestr-4-en-17β-ol-3-one; 7α,11β-Dimethyl-19-norandrost-4-en-17β-ol-3-one |
| Routes of administration | By mouth |
| Drug class | Androgen;Anabolic steroid;Progestogen |
| Identifiers | |
| |
| CAS Number |
|
| PubChemCID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard(EPA) | |
| Chemical and physical data | |
| Formula | C20H30O2 |
| Molar mass | 302.458 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
Dimethandrolone (DMA), also known by its developmental code nameCDB-1321, is an experimentalandrogen/anabolic steroid (AAS) andprogestogen medication which is under investigation for potential clinical use.[1][2][3]
Dimethandrolone is an AAS, and hence is anagonist of theandrogen receptor, thebiological target of androgens liketestosterone.[1] It is also aprogestin, or asynthetic progestogen, and hence is an agonist of theprogesterone receptor, the biological target of progestogens likeprogesterone.[1] Due to its androgenic and progestogenic activity, dimethandrolone hasantigonadotropic effects.[1] It has noestrogenic activity.[1][4]
Dimethandrolone was first described in 1997.[5] It was developed by the Contraceptive Development Branch of theNational Institute of Child Health and Human Development, an agency in theUnited States government.[1][6]
Anester andprodrug of dimethandrolone,dimethandrolone undecanoate (DMAU) (CDB-4521), is under development for potential use as abirth control pillfor men and inandrogen replacement therapy for men.[1][2][3][7]
Dimethandrolone is an AAS, though it has also been described as aselective androgen receptor modulator (SARM).[1][2][3] As an AAS, it is apotentagonist of theandrogen receptor (AR).[1][2]
Unliketestosterone and various other AAS, dimethandrolone is notmetabolized by5α-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 AR, indicating that dimethandrolone does not require potentiation by 5α-reductase for its activity as an AAS and that even if it were asubstrate for 5α-reductase, it would not be potentiated in androgenic tissues like theskin andprostate.[2] As such, dimethandrolone and ester prodrugs of it like DMAU are thought to have a reduced risk of androgenicside effects andconditions such asbenign prostatic hyperplasia,prostate cancer,pattern scalp hair loss, andacne relative to testosterone and certain other AAS.[2]
Dimethandrolone is not a substrate foraromatase, and for this reason, is not converted into the correspondingaromatic A-ringderivative 7α,11β-dimethylestradiol, a potentestrogen.[3][4] As such, dimethandrolone is not estrogenic.[4] This is in contrast to nandrolone, which, although its rate of aromatization into the estrogenestradiol is reduced relative to that of testosterone, is still converted to a significant extent.[4]
Similarly to nandrolone and other 19-nortestosterone derivatives, dimethandrolone is a potent progestogen in addition to AAS.[1] This property may serve to augment itsantigonadotropic activity, which in turn may improve its effectiveness as anantispermatogenic agent and male contraceptive.[1] This is salient and potentially beneficial as male contraceptives based on androgens alone have failed to produce satisfactoryazoospermia in around one-third of men.[1]
Dimethandrolone has shown minimal potential forhepatotoxicity in animal studies, which is in accordance with the fact that it is not a17α-alkylated AAS.[6]
Dimethandrolone, also known as 7α,11β-dimethyl-19-nortestosterone or as 7α,11β-dimethylestr-4-en-17β-ol-3-one, is asyntheticestranesteroid and a non-17α-alkylatedderivative ofnandrolone (19-nortestosterone).[1]
Aside from the C17βundecanoateester of dimethandrolone, DMAU (CDB-4521),[1][2][3] a few other esters, such asdimethandrolone buciclate (CDB-4386A) anddimethandrolone dodecylcarbonate (CDB-4730), have also been developed.[8][9]
Other AAS that are closely related to dimethandrolone (besides nandrolone) includetrestolone (also known as 7α-methyl-19-nortestosterone (MENT)) and11β-methyl-19-nortestosterone (11β-MNT) and their respective C17β esterstrestolone acetate and11β-MNT dodecylcarbonate (11β-MNTDC).[1][2]
Apatent for dimethandrolone was filed in 1997 and was granted in 1999.[5] Subsequently, a patent for DMAU anddimethandrolone buciclate was filed in 2002 and was granted to theUnited States government in 2003.[8] Dimethandrolone was developed under the code name CDB-1321 by the Contraceptive Development Branch of theNational Institute of Child Health and Human Development, one of theNational Institutes of Health in theUnited States Department of Health and Human Services.[1][6]
