Norgestrienone
Chemical compound From Wikipedia, the free encyclopedia
Chemical compound From Wikipedia, the free encyclopedia
Norgestrienone, sold under the brand names Ogyline, Planor, and Miniplanor, is a progestin medication which has been used in birth control pills, sometimes in combination with ethinylestradiol.[1][2][3][4][5] It was developed by Roussel Uclaf and has been registered for use only in France.[4][5][6] Under the brand name Planor, it has been marketed in France as 2 mg norgestrienone and 50 μg ethinylestradiol tablets.[7] It is taken by mouth.[5]
Clinical data | |
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Trade names | Ogyline, Planor, Miniplanor |
Other names | RU-2010; A-301; 17α-Ethynyltrienolone; 17α-Ethynyltrenbolone; Δ9,11-Norethisterone; 17α-Ethynylestra-4,9,11-trien-17β-ol-3-one |
Routes of administration | By mouth |
Drug class | Progestogen; Progestin; Androgen; Anabolic steroid |
ATC code | |
Identifiers | |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.011.544 |
Chemical and physical data | |
Formula | C20H22O2 |
Molar mass | 294.394 g·mol−1 |
3D model (JSmol) | |
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Norgestrienone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[8] It has some androgenic activity.[9][10][11][12]
Norgestrienone was first described in the literature in 1965.[10] It is sometimes referred to as a "second-generation" progestin.[13] Norgestrienone is no longer available.[citation needed]
Norgestrienone was used in hormonal contraception to prevent pregnancy.[2][7] It has typically been used as an oral contraceptive at a dosage of 2 mg/day in combination with ethinylestradiol and 350 μ/day when used alone.[5]
Norgestrienone has been found to possess similar affinity for the progesterone receptor and androgen receptor,[8] and in accordance, has some androgenic activity.[9][10][11][12] The androgenic activity of norgestrienone is greater than that of other 19-nortestosterone derivatives due to the presence of the C9(11) double bond, which enhances said activity.[12] The ratio of progestogenic to androgenic activity appears to be much lower for norgestrienone that it is for other 19-nortestosterone progestins such as norethisterone and levonorgestrel.[14][15][16][17] Gestrinone, the 18-methyl analogue of norgestrienone, has even greater androgenic activity than norgestrienone, as this modification increases androgenic activity similarly.[12]
Compound | PR | AR | ER | GR | MR | SHBG | CBG | |
---|---|---|---|---|---|---|---|---|
Norethisterone | 155–156 | 43–45 | <0.1 | 2.7–2.8 | 0.2 | ? | ? | |
Norgestrienone | 63–65 | 70 | <0.1 | 11 | 1.8 | ? | ? | |
Levonorgestrel | 170 | 84–87 | <0.1 | 14 | 0.6–0.9 | ? | ? | |
Gestrinone | 75–76 | 83–85 | <0.1, 3–10 | 77 | 3.2 | ? | ? | |
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PR , testosterone for the AR , E2 for the ER , DEXA for the GR , aldosterone for the MR , DHT for SHBG , and cortisol for CBG . Sources: [14][15][16][17] |
The metabolism of norgestrienone in humans has been studied.[18]
Norgestrienone, also known as 17α-ethynyl-19-nor-δ9,11-testosterone or as 17α-ethynylestra-4,9,11-trien-17β-ol-3-one, as well as δ9,11-norethisterone or 17α-ethynyltrienolone (17α-ethynyltrenbolone), is a synthetic estrane steroid and a derivative of testosterone and 19-nortestosterone.[1][4][19] It is structurally related to the anabolic steroid trenbolone (19-nor-δ9,11-testosterone; the non-17α-ethynylated analogue of norgestrienone), the progestogenic and androgenic steroid gestrinone (the 13β-ethyl variant or 18-methyl derivative of norgestrienone), and the anabolic steroid tetrahydrogestrinone (the 18-methyl and 17α-ethyl variant of norgestrienone).[1][4][20]
Norgestrienone was first described in the literature in 1965.[10] It is sometimes referred to as a "second-generation" progestin based on its time of introduction.[13]
Norgestrienone is the generic name of the drug and its INN .[1][2][4] It is also known by its developmental code names RU-2010 and A-301.[1][2][4]
Norgestrienone has been marketed under the brand names Ogyline, Planor, and Miniplanor.[1][2][4]
Norgestrienone is no longer marketed and hence is no longer available in any country.[citation needed] It was previously used in France.[4] The medication was never marketed in the United States.[21]
Norgestrienone has been studied for use in male hormonal contraception.[22]
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