Английская Википедия:Etynodiol diacetate
Шаблон:Short description Шаблон:Use dmy dates Шаблон:Cs1 config Шаблон:Infobox drug
Etynodiol diacetate, or ethynodiol diacetate, sold under the brand name Ovulen among others, is a progestin medication which is used in birth control pills.[1][2][3] The medication is available only in combination with an estrogen.[4] It is taken by mouth.[5]
Etynodiol diacetate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[6][7] It has weak androgenic and estrogenic activity and no other important hormonal activity.[8][9][10] The medication is a prodrug of norethisterone in the body, with etynodiol occurring as an intermediate.[6][7][11]
Etynodiol, a related compound, was discovered in 1954, and etynodiol diacetate was introduced for medical use in 1965.[12][13] The combination ethynodiol with mestranol (Ovulen) was approved for medical use in the United States in 1966.[14] The combination ethinylestradiol with ethynodiol (Demulen) was approved for medical use in the United States in 1970.[15]
In 2021, the combination with ethinylestradiol was the 276th most commonly prescribed medication in the United States, with more than 800,000 prescriptions.[16][17]
Medical uses
Etynodiol diacetate is used in combination with an estrogen such as ethinylestradiol or mestranol in combined oral contraceptives for women for the prevention of pregnancy.[5]
Side effects
Pharmacology
Etynodiol diacetate is virtually inactive in terms of affinity for the progesterone and androgen receptors and acts as a rapidly converted prodrug of norethisterone, with etynodiol occurring as an intermediate.[6][7][11] Upon oral administration and during first-pass metabolism in the liver, etynodiol diacetate is rapidly converted by esterases into etynodiol,[11] which is followed by oxygenation of the C3 hydroxyl group to produce norethisterone.[7] In addition to its progestogenic activity, etynodiol diacetate has weak androgenic activity,[8][9] and, unlike most progestins but similarly to norethisterone and noretynodrel,[18] also has some estrogenic activity.[9][10]
The pharmacokinetics of etynodiol diacetate have been reviewed.[19]
Шаблон:Relative affinities of norethisterone, metabolites, and prodrugs
Chemistry
Etynodiol diacetate, also known as 3β-hydroxy-17α-ethynyl-19-nortestosterone 3β,17β-diaceate, 3β-hydroxynorethisterone 3β,17β-diacetate, or 17α-ethynylestr-4-ene-3β,17β-diol 3β,17β-diacetate, is a synthetic estrane steroid and a derivative of testosterone.[20][2][3] It is specifically a derivative of 19-nortestosterone and 17α-ethynyltestosterone, or of norethisterone (17α-ethynyl-19-nortestosterone), in which the C3 ketone group has been dehydrogenated into a C3β hydroxyl group and acetate esters have been attached at the C3β and C17β positions.[2][3] Etynodiol diacetate is the 3β,17β-diacetate ester of etynodiol (17α-ethynylestr-4-ene-3β,17β-diol).[2][3]
Synthesis
Chemical syntheses of etynodiol diacetate have been published.[19]
Reduction of norethisterone (1) affords the 3,17-diol. The 3β-hydroxy compound is the desired product; since reactions at C3 do not show nearly the stereoselectivity as those at C17 by virtue of the relative lack of stereo-directing proximate substituents, the formation of the desired isomer is engendered by use of a bulky reducing agent, lithium tri-tert-butoxyaluminum hydride. Acetylation of the 3β,17β-diol affords etynodiol diacetate (3).[21]
History
Etynodiol was first synthesized in 1954, via reduction of norethisterone, and etynodiol diacetate was introduced for medical use in 1965.[12][13]
Society and culture
Generic names
Etynodiol diacetate is the generic name of the drug (the Шаблон:Abbrlink of its free alcohol form is etynodiol), while ethynodiol diacetate is its Шаблон:Abbrlink, Шаблон:Abbrlink, and Шаблон:Abbrlink.[2][3][4] It is also known by its former developmental code names CB-8080 and SC-11800.[2][3][4]
Brand names
Etynodiol diacetate is or has been marketed under brand names including Conova, Continuin, Demulen,[15][23] Femulen, Kelnor,[24][23] Lo-Malmorede,[25] Luteonorm, Luto-Metrodiol, Malmorede,[26] Metrodiol, Ovulen,[14][23] Soluna, Zovia,[27] and others.[2][3][4]
Availability
Etynodiol diacetate is marketed in only a few countries, including the United States, Canada, Argentina, and Oman.[4]
References
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- ↑ Шаблон:Cite book
- ↑ 2,0 2,1 2,2 2,3 2,4 2,5 2,6 Шаблон:Cite book
- ↑ 3,0 3,1 3,2 3,3 3,4 3,5 3,6 Шаблон:Cite book
- ↑ 4,0 4,1 4,2 4,3 4,4 Шаблон:Cite web
- ↑ 5,0 5,1 Шаблон:Cite book
- ↑ 6,0 6,1 6,2 Шаблон:Cite journal
- ↑ 7,0 7,1 7,2 7,3 Шаблон:Cite book
- ↑ 8,0 8,1 Шаблон:Cite book
- ↑ 9,0 9,1 9,2 Шаблон:Cite book
- ↑ 10,0 10,1 Шаблон:Cite book
- ↑ 11,0 11,1 11,2 Шаблон:Cite journal
- ↑ 12,0 12,1 Шаблон:Cite journal
- ↑ 13,0 13,1 Шаблон:Cite book
- ↑ 14,0 14,1 Шаблон:Cite web
- ↑ 15,0 15,1 Шаблон:Cite web
- ↑ Шаблон:Cite web
- ↑ Шаблон:Cite web
- ↑ Шаблон:Cite book
- ↑ 19,0 19,1 Шаблон:Cite book
- ↑ Ошибка цитирования Неверный тег
<ref>
; для сносокSchindlerCampagnoli2003
не указан текст - ↑ 21,0 21,1 Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ 23,0 23,1 23,2 Шаблон:Cite web
- ↑ Ошибка цитирования Неверный тег
<ref>
; для сносокKelnor FDA label
не указан текст - ↑ Шаблон:Cite web
- ↑ Шаблон:Cite web
- ↑ Ошибка цитирования Неверный тег
<ref>
; для сносокZovia FDA label
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