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Clinical data | |
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Other names | Allylnortestosterone; Allylestrenolone; Allylnandrolone; 3-Ketoallylestrenol; 17α-Allylestr-4-en-17β-ol-3-one; Allylestrenolone |
Drug class | Progestogen |
Identifiers | |
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CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
Chemical and physical data | |
Formula | C21H30O2 |
Molar mass | 314.469 g·mol−1 |
3D model ( JSmol) | |
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17α-Allyl-19-nortestosterone, also known as 3-ketoallylestrenol or as 17α-allylestr-4-en-17β-ol-3-one, is a progestin which was never marketed. [1] [2] [3] [4] It is a combined derivative of the anabolic–androgenic steroid and progestogen nandrolone (19-nortestosterone) and the antiandrogen allyltestosterone (17α-allyltestosterone). [1] [2] [3] The drug is a major active metabolite of allylestrenol, which is thought to be a prodrug of 17α-allyl-19-nortestosterone. [4] [5]
17α-Allyl-19-nortestosterone has 24% of the affinity of ORG-2058 and 186% of the affinity of progesterone for the progesterone receptor, 4.5% of the affinity of testosterone for the androgen receptor, 9.8% of the affinity of dexamethasone for the glucocorticoid receptor, 2.8% of the affinity of testosterone for sex hormone-binding globulin, and less than 0.2% of the affinity of estradiol for the estrogen receptor. [6] [7] The affinity of 17α-allyl-19-nortestosterone for the androgen receptor was less than that of norethisterone and medroxyprogesterone acetate and its affinity for sex hormone-binding globulin was much lower than that of norethisterone. [6] These findings may help to explain the absence of teratogenic effects of allylestrenol on the external genitalia of female and male rat fetuses. [6]
Compound | PR | AR | ER | GR | MR | SHBG | CBG | |
---|---|---|---|---|---|---|---|---|
Allylestrenol | 0 | 0 | 0 | 0 | ? | 1 | ? | |
17α-Allyl-19-NT | 186 | 5 | 0 | 10 | ? | 3 | ? | |
Values are percentages (%). Reference ligands (100%) were P4 for the PR , T for the AR , E2 for the ER , DEXA for the GR , aldosterone for the MR , T for SHBG , and cortisol for CBG . |
Other examples are allylestrenol (42), a pro-drug converted to the 3-keto analogue (43), which is used in the treatment of threatened abortion [78,79] and altrenogest (44), used in sows and mares to suppress ovulation and estrus behaviour [80]. [...] Progestins with a 17a-allyl side chain: (42) allylestrenol, (43), (44) altrenogest.
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Clinical data | |
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Other names | Allylnortestosterone; Allylestrenolone; Allylnandrolone; 3-Ketoallylestrenol; 17α-Allylestr-4-en-17β-ol-3-one; Allylestrenolone |
Drug class | Progestogen |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
Chemical and physical data | |
Formula | C21H30O2 |
Molar mass | 314.469 g·mol−1 |
3D model ( JSmol) | |
| |
|
17α-Allyl-19-nortestosterone, also known as 3-ketoallylestrenol or as 17α-allylestr-4-en-17β-ol-3-one, is a progestin which was never marketed. [1] [2] [3] [4] It is a combined derivative of the anabolic–androgenic steroid and progestogen nandrolone (19-nortestosterone) and the antiandrogen allyltestosterone (17α-allyltestosterone). [1] [2] [3] The drug is a major active metabolite of allylestrenol, which is thought to be a prodrug of 17α-allyl-19-nortestosterone. [4] [5]
17α-Allyl-19-nortestosterone has 24% of the affinity of ORG-2058 and 186% of the affinity of progesterone for the progesterone receptor, 4.5% of the affinity of testosterone for the androgen receptor, 9.8% of the affinity of dexamethasone for the glucocorticoid receptor, 2.8% of the affinity of testosterone for sex hormone-binding globulin, and less than 0.2% of the affinity of estradiol for the estrogen receptor. [6] [7] The affinity of 17α-allyl-19-nortestosterone for the androgen receptor was less than that of norethisterone and medroxyprogesterone acetate and its affinity for sex hormone-binding globulin was much lower than that of norethisterone. [6] These findings may help to explain the absence of teratogenic effects of allylestrenol on the external genitalia of female and male rat fetuses. [6]
Compound | PR | AR | ER | GR | MR | SHBG | CBG | |
---|---|---|---|---|---|---|---|---|
Allylestrenol | 0 | 0 | 0 | 0 | ? | 1 | ? | |
17α-Allyl-19-NT | 186 | 5 | 0 | 10 | ? | 3 | ? | |
Values are percentages (%). Reference ligands (100%) were P4 for the PR , T for the AR , E2 for the ER , DEXA for the GR , aldosterone for the MR , T for SHBG , and cortisol for CBG . |
Other examples are allylestrenol (42), a pro-drug converted to the 3-keto analogue (43), which is used in the treatment of threatened abortion [78,79] and altrenogest (44), used in sows and mares to suppress ovulation and estrus behaviour [80]. [...] Progestins with a 17a-allyl side chain: (42) allylestrenol, (43), (44) altrenogest.