Quinestrol, also known as ethinylestradiol cyclopentyl ether (EECPE), sold under the brand name Estrovis among others, is an estrogen medication which has been used in menopausal hormone therapy, hormonal birth control, and to treat breast cancer and prostate cancer.[2][3] It is taken once per week to once per month by mouth.[4][5][6][7]
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Trade names | Estrovis, others |
Other names | Quinoestrol; Quinestrenol; Quinoestrenol; Ethinylestradiol 3-cyclopentyl ether; EECPE; EE2CPE; W-3566; 3-(Cyclopentyloxy)-17α-ethynylestra-1,3,5(10)-trien-17β-ol |
AHFS/Drugs.com | Micromedex Detailed Consumer Information |
Routes of administration | By mouth |
Drug class | Estrogen; Estrogen ether |
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Elimination half-life | >120 hours (>5 days)[1] |
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ECHA InfoCard | 100.005.277 |
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Formula | C25H32O2 |
Molar mass | 364.529 g·mol−1 |
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Quinestrol has been used as the estrogen component in menopausal hormone therapy and in combined hormonal birth control.[2][3] It has also occasionally been used in the treatment of breast cancer and prostate cancer, as well as to suppress lactation.[2][3][8] On its own as an estrogen, quinestrol was taken once per week by mouth.[4] As a combined birth control pill, it was used together with quingestanol acetate and was taken once per month by mouth.[5][6][7]
Quinestrol is a prodrug of ethinylestradiol (EE), with no estrogenic activity of its own.[3][9][10] It is taken orally and has prolonged activity following a single dose,[9][10] with a very long biological half-life of more than 120 hours (5 days) due to enhanced lipophilicity and storage in fat.[3][1] Because of its much longer half-life, quinestrol is two to three times as potent as EE.[3] Also because of its long half-life, quinestrol can be taken once a week or once a month.[3][4][5][6][7]
Following administration, quinestrol is absorbed via the lymphatic system, is stored in adipose tissue, and is gradually released from adipose tissue.[11]
Estrogen | Other names | RBA (%)a | REP (%)b | |||
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ER | ERα | ERβ | ||||
Estradiol | E2 | 100 | 100 | 100 | ||
Estradiol 3-sulfate | E2S; E2-3S | ? | 0.02 | 0.04 | ||
Estradiol 3-glucuronide | E2-3G | ? | 0.02 | 0.09 | ||
Estradiol 17β-glucuronide | E2-17G | ? | 0.002 | 0.0002 | ||
Estradiol benzoate | EB; Estradiol 3-benzoate | 10 | 1.1 | 0.52 | ||
Estradiol 17β-acetate | E2-17A | 31–45 | 24 | ? | ||
Estradiol diacetate | EDA; Estradiol 3,17β-diacetate | ? | 0.79 | ? | ||
Estradiol propionate | EP; Estradiol 17β-propionate | 19–26 | 2.6 | ? | ||
Estradiol valerate | EV; Estradiol 17β-valerate | 2–11 | 0.04–21 | ? | ||
Estradiol cypionate | EC; Estradiol 17β-cypionate | ?c | 4.0 | ? | ||
Estradiol palmitate | Estradiol 17β-palmitate | 0 | ? | ? | ||
Estradiol stearate | Estradiol 17β-stearate | 0 | ? | ? | ||
Estrone | E1; 17-Ketoestradiol | 11 | 5.3–38 | 14 | ||
Estrone sulfate | E1S; Estrone 3-sulfate | 2 | 0.004 | 0.002 | ||
Estrone glucuronide | E1G; Estrone 3-glucuronide | ? | <0.001 | 0.0006 | ||
Ethinylestradiol | EE; 17α-Ethynylestradiol | 100 | 17–150 | 129 | ||
Mestranol | EE 3-methyl ether | 1 | 1.3–8.2 | 0.16 | ||
Quinestrol | EE 3-cyclopentyl ether | ? | 0.37 | ? | ||
Footnotes: a = Relative binding affinities (RBAs) were determined via in-vitro displacement of labeled estradiol from estrogen receptors (ERs) generally of rodent uterine cytosol. Estrogen esters are variably hydrolyzed into estrogens in these systems (shorter ester chain length -> greater rate of hydrolysis) and the ER RBAs of the esters decrease strongly when hydrolysis is prevented. b = Relative estrogenic potencies (REPs) were calculated from half-maximal effective concentrations (EC50) that were determined via in-vitro β‐galactosidase (β-gal) and green fluorescent protein (GFP) production assays in yeast expressing human ERα and human ERβ. Both mammalian cells and yeast have the capacity to hydrolyze estrogen esters. c = The affinities of estradiol cypionate for the ERs are similar to those of estradiol valerate and estradiol benzoate (figure). Sources: See template page. |
Compound | Dosage for specific uses (mg usually)[a] | ||||||
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ETD[b] | EPD[b] | MSD[b] | MSD[c] | OID[c] | TSD[c] | ||
Estradiol (non-micronized) | 30 | ≥120–300 | 120 | 6 | - | - | |
Estradiol (micronized) | 6–12 | 60–80 | 14–42 | 1–2 | >5 | >8 | |
Estradiol valerate | 6–12 | 60–80 | 14–42 | 1–2 | - | >8 | |
Estradiol benzoate | - | 60–140 | - | - | - | - | |
Estriol | ≥20 | 120–150[d] | 28–126 | 1–6 | >5 | - | |
Estriol succinate | - | 140–150[d] | 28–126 | 2–6 | - | - | |
Estrone sulfate | 12 | 60 | 42 | 2 | - | - | |
Conjugated estrogens | 5–12 | 60–80 | 8.4–25 | 0.625–1.25 | >3.75 | 7.5 | |
Ethinylestradiol | 200 μg | 1–2 | 280 μg | 20–40 μg | 100 μg | 100 μg | |
Mestranol | 300 μg | 1.5–3.0 | 300–600 μg | 25–30 μg | >80 μg | - | |
Quinestrol | 300 μg | 2–4 | 500 μg | 25–50 μg | - | - | |
Methylestradiol | - | 2 | - | - | - | - | |
Diethylstilbestrol | 2.5 | 20–30 | 11 | 0.5–2.0 | >5 | 3 | |
DES dipropionate | - | 15–30 | - | - | - | - | |
Dienestrol | 5 | 30–40 | 42 | 0.5–4.0 | - | - | |
Dienestrol diacetate | 3–5 | 30–60 | - | - | - | - | |
Hexestrol | - | 70–110 | - | - | - | - | |
Chlorotrianisene | - | >100 | - | - | >48 | - | |
Methallenestril | - | 400 | - | - | - | - | |
Quinestrol, also known as ethinylestradiol 3-cyclopentyl ether (EE2CPE), is a synthetic estrane steroid and a derivative of estradiol.[31][32] It is an estrogen ether, specifically the C3 cyclopentyl ether of ethinylestradiol (17α-ethynylestradiol).[31][32] Closely related estrogens include mestranol (ethinylestradiol 3-methyl ether) and ethinylestradiol sulfonate (EES; Turisteron; ethinylestradiol 3-isopropylsulfonate).[31][32]
Quinestrol was developed and introduced for medical use in the 1960s.[33]
Quinestrol is the generic name of the drug and its INN , USAN , and BAN .[31][32][34][35] It is also known by its former developmental code name W-3566.[31][32][34][35]
Quinestrol has been marketed under brand names including Agalacto-Quilea, Basaquines, Eston, Estrovis, Estrovister, Plestrovis, Qui-Lea, Soluna, and Yueketing, among others.[31][32][34][35]
Quinestrol was marketed as Estrovis in the United States by Parke-Davis and as Qui-Lea in Argentina,[32] but is reportedly not currently marketed.[3] However, it does appear to still be available as an oral contraceptive in combination with progestins in Argentina and China.[35]
One tablet form available in China consists of 6 mg levonorgestrel and 3 mg quinestrol; it is used as a prescription "long-term" oral contraceptive, with one dose taken each month.[35][36] It is sold under various brand names including Yuèkětíng (Chinese: 悦可婷) and Àiyuè (Chinese: 艾悦). A version with the racemic norgestrel in place of levonorgestrel also appears to be available.[35]
The Chinese levonorgestrel/quinestrol 2:1 formula is known as EP-1 in veterinary practice. It is known to have some organ-specific effects on the Mongolian gerbil as measured by receptor mRNA expression.[37] Incorporated into baits at a concentration of 50 ppm, EP-1 has been used to control wild Mongolian gerbil populations with some success.[38]
There is no doubt that the conversion of the endometrium with injections of both synthetic and native estrogenic hormone preparations succeeds, but the opinion whether native, orally administered preparations can produce a proliferation mucosa changes with different authors. PEDERSEN-BJERGAARD (1939) was able to show that 90% of the folliculin taken up in the blood of the vena portae is inactivated in the liver. Neither KAUFMANN (1933, 1935), RAUSCHER (1939, 1942) nor HERRNBERGER (1941) succeeded in bringing a castration endometrium into proliferation using large doses of orally administered preparations of estrone or estradiol. Other results are reported by NEUSTAEDTER (1939), LAUTERWEIN (1940) and FERIN (1941); they succeeded in converting an atrophic castration endometrium into an unambiguous proliferation mucosa with 120–300 oestradiol or with 380 oestrone.
[...] J. Fertil., 1967, 12, 2) contains 23 papers presented at a symposium on QUINESTROL. Quinestrol is a newly-developed synthetic steroid, and is the cyclo-pentyl ether of a ethinyl oestradiol.
When taking the medicine for the first time, take the medicine once after lunch on the fifth day counting from the day of menstrual cramps, and take the second medicine at an interval of 20 days. Afterwards, take the second medicine taking day as the monthly medicine taking date, and take one tablet every month. When changing from short-acting oral contraceptives to long-acting contraceptives, you can take one long-acting contraceptive the next day after taking 22 tablets, and then take one tablet every month on the same day you started taking long-acting contraceptives.