Quinestrol Explained

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.[1] It is taken once per week to once per month by mouth.

Medical uses

Quinestrol has been used as the estrogen component in menopausal hormone therapy and in combined hormonal birth control. It has also occasionally been used in the treatment of breast cancer and prostate cancer, as well as to suppress lactation.[2] On its own as an estrogen, quinestrol was taken once per week by mouth.[3] As a combined birth control pill, it was used together with quingestanol acetate and was taken once per month by mouth.[4] [5] [6]

Pharmacology

Quinestrol is a prodrug of ethinylestradiol (EE), with no estrogenic activity of its own.[7] [8] It is taken orally and has prolonged activity following a single dose, with a very long biological half-life of more than 120 hours (5 days) due to enhanced lipophilicity and storage in fat.[9] Because of its much longer half-life, quinestrol is two to three times as potent as EE.[10] Also because of its long half-life, quinestrol can be taken once a week or once a month.

Following administration, quinestrol is absorbed via the lymphatic system, is stored in adipose tissue, and is gradually released from adipose tissue.[11]

Chemistry

Quinestrol, also known as ethinylestradiol 3-cyclopentyl ether (EE2CPE), is a synthetic estrane steroid and a derivative of estradiol. It is an estrogen ether, specifically the C3 cyclopentyl ether of ethinylestradiol (17α-ethynylestradiol). Closely related estrogens include mestranol (ethinylestradiol 3-methyl ether) and ethinylestradiol sulfonate (EES; Turisteron; ethinylestradiol 3-isopropylsulfonate).

History

Quinestrol was developed and introduced for medical use in the 1960s.[12]

Society and culture

Generic names

Quinestrol is the generic name of the drug and its,, and .[13] [14] [15] [16] It is also known by its former developmental code name W-3566.

Brand names

Quinestrol has been marketed under brand names including Agalacto-Quilea, Basaquines, Eston, Estrovis, Estrovister, Plestrovis, Qui-Lea, Soluna, and Yueketing, among others.

Availability

Quinestrol was marketed as Estrovis in the United States by Parke-Davis and as Qui-Lea in Argentina, but is reportedly not currently marketed. However, it does appear to still be available as an oral contraceptive in combination with progestins in Argentina and China.

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.[16] [17] It is sold under various brand names including Yuèkětíng and Àiyuè . A version with the racemic norgestrel in place of levonorgestrel also appears to be available.[16]

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.[18] Incorporated into baits at a concentration of 50 ppm, EP-1 has been used to control wild Mongolian gerbil populations with some success.[19]

Notes and References

  1. Book: Zink C . Quinestrol . Dictionary of Obstetrics and Gynecology. https://books.google.com/books?id=EQlvzV9V7xIC&pg=PA204. 1 January 1988. Walter de Gruyter. 978-3-11-085727-6. 204–.
  2. Book: Vorherr H . The Breast: Morphology, Physiology, and Lactation. 2 December 2012. Elsevier Science. 978-0-323-15726-1. 201–203.
  3. Book: Quirk Jr JG, Wendel Jr GD . Biologic effects of natural and synthetic estrogens. . Buchsbaum HJ . The Menopause. https://books.google.com/books?id=z0LuBwAAQBAJ&pg=PA60 . 6 December 2012. Springer Science & Business Media. 978-1-4612-5525-3. 60–.
  4. Book: Horsky . Contraception . Horsky J, Presl J . Ovarian Function and its Disorders: Diagnosis and Therapy. https://books.google.com/books?id=7IrpCAAAQBAJ&pg=PA367. 6 December 2012. Springer Science & Business Media. 978-94-009-8195-9. 85,358,367.
  5. Book: Hawkins DF, Elder MG . Other Hormal Contraception Procedures . Human Fertility Control: Theory and Practice. https://books.google.com/books?id=1lL0AgAAQBAJ&pg=PA92. 22 October 2013. Elsevier Science. 978-1-4831-6361-1. 92–94.
  6. Book: Bennett JP . Chemical Contraception. 18 June 1974. Macmillan International Higher Education. 978-1-349-02287-8. 61–.
  7. Epstein JA . Prolonged menstrual response of patients with gonadal failure following quinestrol administration . International Journal of Fertility . 12 . 2 . 181–186 . 1967 . 6033895 .
  8. Giannina T, Meli A . Prolonged oestrogenic activity in rats after single oral administration of ethinyloestradiol-3-cyclopentyl ether . The Journal of Pharmacy and Pharmacology . 21 . 4 . 271–272 . April 1969 . 4390151 . 10.1111/j.2042-7158.1969.tb08247.x . 19407816 .
  9. Book: Sitruk-Ware R . Pharmacology of Different Administration Routes-Oral vs Transdermal. . Oettel M, Schillinger E . Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Handbook of Experimental Pharmacology . https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA248 . 6 December 2012. 135 / 2 . Springer Science & Business Media. 978-3-642-60107-1. 248– . 10.1007/978-3-642-60107-1_14 .
  10. Book: Peterson CM, Udoff LC . Primary and secondary hypogonadism in women. . Meikle AW . Hormone Replacement Therapy. https://books.google.com/books?id=ja2nBgAAQBAJ&pg=PA381. 1 June 1999. Springer Science & Business Media. 978-1-59259-700-0. 381–.
  11. Hammond CB, Maxson WS . Current status of estrogen therapy for the menopause . Fertility and Sterility . 37 . 1 . 5–25 . January 1982 . 6277697 . 10.1016/S0015-0282(16)45970-4 .
  12. Book: Medical Gynaecology and Sociology. 1967. Medical and Scientific Services Limited. [...] 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..
  13. Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 522–.
  14. Book: Quinestrol . Index Nominum 2000: International Drug Directory. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA905. January 2000. Taylor & Francis. 978-3-88763-075-1. 905–.
  15. Book: Morton IK, Hall JM . Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 6 December 2012. Springer Science & Business Media. 978-94-011-4439-1. 243–.
  16. Web site: Quinestrol . Drugs.com . https://web.archive.org/web/20151020003656/https://www.drugs.com/international/quinestrol.html . 20 October 2015.
  17. Web site: 悦可婷 左炔诺孕酮炔雌醚片 6片/盒 . Yueketing Levonorgestrel Ethinylestradiol Tablets 6 Pieces/Box . Chinese . Tmall. https://archive.today/20180716053328/https://detail.yao.95095.com/item.htm?id=528371420852. 2018-07-16. 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. .
  18. Lv X, Shi D . Combined effects of levonorgestrel and quinestrol on reproductive hormone levels and receptor expression in females of the Mongolian gerbil (Meriones unguiculatus) . Zoological Science . 29 . 1 . 37–42 . January 2012 . 22233494 . 10.2108/zsj.29.37 . 22347486 .
  19. Fu H, Zhang J, Shi D, Wu X . Effects of levonorgestrel-quinestrol (EP-1) treatment on Mongolian gerbil wild populations: a case study . Integrative Zoology . 8 . 3 . 277–284 . September 2013 . 24020466 . 10.1111/1749-4877.12018 .

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