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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 as testosterone 17β-(1-((5-(aminosulfonyl)-2-pyridinyl)carbonyl)-L-proline), is an androgen and anabolic steroid which is under development by Evestra for use in androgen replacement therapy in men. [1] [2] It is an orally active androgen ester – specifically, a C17β sulfonamide– proline ester of the natural and bioidentical androgen testosterone – and acts as a prodrug of testosterone in the body. [2] However, unlike oral testosterone and conventional oral testosterone esters such as testosterone undecanoate, EC586 has high oral potency, may undergo little or no first-pass metabolism, and may not have disproportionate androgenic effects in the liver. [2] [3] As such, it may have a variety of desirable advantages over oral testosterone, similarly to parenteral testosterone, but with the convenience of oral administration. [2] [3] Evestra intends to seek Investigational New Drug status for EC586 in the fourth quarter of 2018.[ needs update] [1]
The pharmacokinetics of oral EC586 have been briefly assessed in rats in a small pilot study. [2] Oral EC586 showed area-under-the-curve (AUC) levels that were more than 100-fold greater than those of oral testosterone propionate, the C17β propionate 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–proline estradiol ester known as EC508, which shows the same properties as EC586. [2] [3]
Clinical trials for EC586 and EC508 are undergoing as of 2023. [4]
EC586: Testosterone prodrug
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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 |
Identifiers | |
| |
CAS Number | |
UNII | |
Chemical and physical data | |
Formula | C30H39N3O6S |
Molar mass | 569.72 g·mol−1 |
3D model ( JSmol) | |
| |
|
EC586, also known as testosterone 17β-(1-((5-(aminosulfonyl)-2-pyridinyl)carbonyl)-L-proline), is an androgen and anabolic steroid which is under development by Evestra for use in androgen replacement therapy in men. [1] [2] It is an orally active androgen ester – specifically, a C17β sulfonamide– proline ester of the natural and bioidentical androgen testosterone – and acts as a prodrug of testosterone in the body. [2] However, unlike oral testosterone and conventional oral testosterone esters such as testosterone undecanoate, EC586 has high oral potency, may undergo little or no first-pass metabolism, and may not have disproportionate androgenic effects in the liver. [2] [3] As such, it may have a variety of desirable advantages over oral testosterone, similarly to parenteral testosterone, but with the convenience of oral administration. [2] [3] Evestra intends to seek Investigational New Drug status for EC586 in the fourth quarter of 2018.[ needs update] [1]
The pharmacokinetics of oral EC586 have been briefly assessed in rats in a small pilot study. [2] Oral EC586 showed area-under-the-curve (AUC) levels that were more than 100-fold greater than those of oral testosterone propionate, the C17β propionate 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–proline estradiol ester known as EC508, which shows the same properties as EC586. [2] [3]
Clinical trials for EC586 and EC508 are undergoing as of 2023. [4]
EC586: Testosterone prodrug