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Chemical compound From Wikipedia, the free encyclopedia
5α-Dihydrolevonorgestrel (5α-DHLNG) is an active metabolite of the progestin levonorgestrel which is formed by 5α-reductase.[1][2] It has about one-third of the affinity of levonorgestrel for the progesterone receptor.[1] In contrast to levonorgestrel, the compound has both progestogenic and antiprogestogenic activity, and hence has a selective progesterone receptor modulator-like profile of activity.[3][4] This is analogous to the case of norethisterone and 5α-dihydronorethisterone.[3][5] In addition to the progesterone receptor, 5α-DHLNG interacts with the androgen receptor.[6] It has similar affinity for the androgen receptor relative to levonorgestrel (34.3% of that of metribolone for levonorgestrel and 38.0% of that of metribolone for 5α-DHLNG), and has androgenic effects similarly to levonorgestrel and testosterone.[6] 5α-DHLNG is further transformed into 3α,5α- and 3β,5α-THLNG, which bind weakly to the estrogen receptor (0.4 to 2.4% of the RBA of E2 ) and have weak estrogenic activity.[7][8][4] These metabolites are considered to be responsible for the weak estrogenic activity of high doses of levonorgestrel.[8][4]
Compound | PR | AR | ER | GR | MR | SHBG | CBG |
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Levonorgestrel | 150–162 | 34a, 45 | 0 | 1–8 | 17–75 | 50 | 0 |
5α-Dihydrolevonorgestrel | 50 | 38a | 0 | ? | ? | ? | ? |
3α,5α-Tetrahydrolevonorgestrel | ? | ? | 0.4 | ? | ? | ? | ? |
3β,5α-Tetrahydrolevonorgestrel | ? | ? | 2.4 | ? | ? | ? | ? |
Notes: Values are percentages (%). Reference ligands (100%) were promegestone for the PR , metribolone (a = mibolerone) for the AR , E2 for the ER , DEXA for the GR , aldosterone for the MR , DHT for SHBG , and cortisol for CBG . Sources: See template. |
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Other names | 5α-Dihydrolevonorgestrel; 5α-DHLNG; 5α-LNG |
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Formula | C21H30O2 |
Molar mass | 314.469 g·mol−1 |
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