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| Clinical data | |
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| Other names | EC-586; Testosterone 17β-(1-[[5-(aminosulfonyl)-2-pyridinyl]carbonyl]-L-proline); Androst-4-en-17β-ol-3-one 17β-(1-[[5-(aminosulfonyl)-2-pyridinyl]carbonyl]-L-proline); 3-Oxoandrost-4-en-17β-yl 1-[[5-(aminosulfonyl)-2-pyridinyl]carbonyl]-L-proline |
| Drug class | Androgen;Anabolic steroid;Androgen ester |
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| Chemical and physical data | |
| Formula | C30H39N3O6S |
| Molar mass | 569.72 g·mol−1 |
| 3D model (JSmol) | |
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EC586, also known astestosterone 17β-(1-((5-(aminosulfonyl)-2-pyridinyl)carbonyl)-L-proline), is anandrogen andanabolic steroid which is under development by Evestra for use inandrogen replacement therapy in men.[1][2] It is anorally activeandrogen ester – specifically, a C17βsulfonamide–prolineester of thenatural andbioidentical androgentestosterone – and acts as aprodrug of testosterone in the body.[2] However, unlike oral testosterone and conventional oral testosterone esters such astestosterone undecanoate, EC586 has high oralpotency, may undergo little or nofirst-pass metabolism, and may not have disproportionate androgenic effects in theliver.[2][3] As such, it may have a variety of desirable advantages over oral testosterone, similarly toparenteral testosterone, but with the convenience of oral administration.[2][3] Evestra intends to seekInvestigational New Drug status for EC586 in the fourth quarter of 2018.[needs update][1]
Thepharmacokinetics of oral EC586 have been briefly assessed in rats in a small pilot study.[2] Oral EC586 showedarea-under-the-curve (AUC) levels that were more than 100-fold greater than those of oraltestosterone propionate, the C17βpropionate ester of testosterone (AUC0-3h = 330 ng/mL and 2.5 ng/mL, respectively, for doses of 3.0 mg/rat each).[2] As such, EC586 would appear to possess strongly increased oral bioavailability, potency, and systemic exposure relative to testosterone propionate.[2] Additional research and details on the pharmacokinetics and properties of EC586 are to be published "soon".[2]
The mechanism for the absence of first-pass metabolism and lack of disproportionate liver exposure with oral administration has been elucidated for a closely related sulfonamide–prolineestradiol ester known asEC508, which shows the same properties as EC586.[2][3]
Clinical trials for EC586 and EC508 are undergoing as of 2023.[4]
EC586: Testosterone prodrug