Quinestrol

Last updated
Quinestrol
Quinestrol.svg
Quinestrol molecule ball.png
Clinical data
Trade names Estrovis, others
Other namesQuinoestrol; 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
ATC code
  • None
Pharmacokinetic data
Elimination half-life >120 hours (>5 days) [1]
Identifiers
  • (8R,9S,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.005.277 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C25H32O2
Molar mass 364.529 g·mol−1
3D model (JSmol)
  • O(c1ccc2c(c1)CC[C@H]3[C@@H]4CC[C@](C#C)(O)[C@@]4(C)CC[C@H]23)C5CCCC5
  • InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1 Yes check.svgY
  • Key:PWZUUYSISTUNDW-VAFBSOEGSA-N Yes check.svgY
   (verify)

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]

Contents

Medical uses

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]

Pharmacology

Ethinylestradiol (EE), the active form of quinestrol. Ethinylestradiol.svg
Ethinylestradiol (EE), the active form of quinestrol.

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]

Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors
Estrogen Other names RBA (%)a REP (%)b
ER ERα ERβ
Estradiol E2100100100
Estradiol 3-sulfate E2S; E2-3S ?0.020.04
Estradiol 3-glucuronide E2-3G ?0.020.09
Estradiol 17β-glucuronide E2-17G ?0.0020.0002
Estradiol benzoate EB; Estradiol 3-benzoate101.10.52
Estradiol 17β-acetate E2-17A31–4524 ?
Estradiol diacetate EDA; Estradiol 3,17β-diacetate ?0.79 ?
Estradiol propionate EP; Estradiol 17β-propionate19–262.6 ?
Estradiol valerate EV; Estradiol 17β-valerate2–110.04–21 ?
Estradiol cypionate EC; Estradiol 17β-cypionate ?c4.0 ?
Estradiol palmitate Estradiol 17β-palmitate0 ? ?
Estradiol stearate Estradiol 17β-stearate0 ? ?
Estrone E1; 17-Ketoestradiol115.3–3814
Estrone sulfate E1S; Estrone 3-sulfate20.0040.002
Estrone glucuronide E1G; Estrone 3-glucuronide ?<0.0010.0006
Ethinylestradiol EE; 17α-Ethynylestradiol10017–150129
Mestranol EE 3-methyl ether11.3–8.20.16
QuinestrolEE 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.
Potencies of oral estrogens [data sources 1]
CompoundDosage for specific uses (mg usually) [lower-alpha 1]
ETD [lower-alpha 2] EPD [lower-alpha 2] MSD [lower-alpha 2] MSD [lower-alpha 3] OID [lower-alpha 3] TSD [lower-alpha 3]
Estradiol (non-micron.) 30≥120–3001206--
Estradiol (micronized) 6–1260–8014–421–2>5>8
Estradiol valerate 6–1260–8014–421–2->8
Estradiol benzoate -60–140----
Estriol ≥20120–150 [lower-alpha 4] 28–1261–6>5-
Estriol succinate -140–150 [lower-alpha 4] 28–1262–6--
Estrone sulfate 1260422--
Conjugated estrogens 5–1260–808.4–250.625–1.25>3.757.5
Ethinylestradiol 200 μg1–2280 μg20–40 μg100 μg100 μg
Mestranol 300 μg1.5–3.0300–600 μg25–30 μg>80 μg-
Quinestrol300 μg2–4500 μg25–50 μg--
Methylestradiol -2----
Diethylstilbestrol 2.520–30110.5–2.0>53
DES dipropionate -15–30----
Dienestrol 530–40420.5–4.0--
Dienestrol diacetate 3–530–60----
Hexestrol -70–110----
Chlorotrianisene ->100-->48-
Methallenestril -400----
Sources and footnotes:
  1. ↑ Dosages are given in milligrams unless otherwise noted.
  2. 1 2 3 Dosed every 2 to 3 weeks
  3. 1 2 3 Dosed daily
  4. 1 2 In divided doses, 3x/day; irregular and atypical proliferation.

Chemistry

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]

History

Quinestrol was developed and introduced for medical use in the 1960s. [33]

Society and culture

Generic names

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]

Brand names

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]

Availability

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]

Veterinary use

Rodents

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]

Related Research Articles

<span class="mw-page-title-main">Progestogen (medication)</span> Medication producing effects similar to progesterone

A progestogen, also referred to as a progestagen, gestagen, or gestogen, is a type of medication which produces effects similar to those of the natural female sex hormone progesterone in the body. A progestin is a synthetic progestogen. Progestogens are used most commonly in hormonal birth control and menopausal hormone therapy. They can also be used in the treatment of gynecological conditions, to support fertility and pregnancy, to lower sex hormone levels for various purposes, and for other indications. Progestogens are used alone or in combination with estrogens. They are available in a wide variety of formulations and for use by many different routes of administration. Examples of progestogens include natural or bioidentical progesterone as well as progestins such as medroxyprogesterone acetate and norethisterone.

<span class="mw-page-title-main">Ethinylestradiol</span> Estrogen medication

Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disorders, and certain hormone-sensitive cancers. It is usually taken by mouth but is also used as a patch and vaginal ring.

<span class="mw-page-title-main">Estradiol valerate</span> Chemical compound

Estradiol valerate (EV), sold for use by mouth under the brand name Progynova and Primiwal E4 and for use by injection under the brand names Delestrogen and Progynon Depot among others, is an estrogen medication. It is used in hormone therapy for menopausal symptoms and low estrogen levels, hormone therapy for transgender people, and in hormonal birth control. It is also used in the treatment of prostate cancer. The medication is taken by mouth or by injection into muscle or fat once every 1 to 4 weeks.

<span class="mw-page-title-main">Norethisterone acetate</span> Chemical compound

Norethisterone acetate (NETA), also known as norethindrone acetate and sold under the brand name Primolut-Nor among others, is a progestin medication which is used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication available in low-dose and high-dose formulations and is used alone or in combination with an estrogen. It is ingested orally.

<span class="mw-page-title-main">Norgestimate</span> Chemical compound

Norgestimate, sold under the brand names Ortho Tri-Cyclen and Previfem among others, is a progestin medication which is used in birth control pills for women and in menopausal hormone therapy. The medication is available in combination with an estrogen and is not available alone. It is taken by mouth.

<span class="mw-page-title-main">Norgestrel</span> Progestin medication used for birth control

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<span class="mw-page-title-main">Gestodene</span> Progestin medication

Gestodene, sold under the brand names Femodene and Minulet among others, is a progestin medication which is used in birth control pills for women. It is also used in menopausal hormone therapy. The medication is available almost exclusively in combination with an estrogen. It is taken by mouth.

<span class="mw-page-title-main">Mestranol</span> Chemical compound

Mestranol, sold under the brand names Enovid, Norinyl, and Ortho-Novum among others, is an estrogen medication which has been used in birth control pills, menopausal hormone therapy, and the treatment of menstrual disorders. It is formulated in combination with a progestin and is not available alone. It is taken by mouth.

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<span class="mw-page-title-main">Norethisterone enanthate</span> Chemical compound

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<span class="mw-page-title-main">Estriol succinate</span> Chemical compound

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<span class="mw-page-title-main">Conjugated estrogens</span> Estrogen medication

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<span class="mw-page-title-main">Methylestradiol</span> Chemical compound

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<span class="mw-page-title-main">Dienestrol diacetate</span> Chemical compound

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<span class="mw-page-title-main">Diethylstilbestrol dipropionate</span> Chemical compound

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<span class="mw-page-title-main">Ethinylestradiol sulfonate</span> Estrogenic drug

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References

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  33. ↑ Medical Gynaecology and Sociology. Medical and Scientific Services Limited. 1967. [...] 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.
  34. 1 2 3 Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 243–. ISBN   978-94-011-4439-1.
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  36. ↑ "悦可婷 左炔诺孕酮炔雌醚片 6片/盒" [Yueketing Levonorgestrel Ethinylestradiol Tablets 6 Pieces/Box]. Tmall (in Chinese). Archived from the original on 2018-07-16. Retrieved 2018-07-16. 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.
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  38. ↑ Fu H, Zhang J, Shi D, Wu X (September 2013). "Effects of levonorgestrel-quinestrol (EP-1) treatment on Mongolian gerbil wild populations: a case study". Integrative Zoology. 8 (3): 277–284. doi:10.1111/1749-4877.12018. PMID   24020466.
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