Quinestrol

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Pharmaceutical drug

title: "Quinestrol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["ethynyl-compounds", "antigonadotropins", "cyclopentyl-ethers", "estranes", "estrogen-ethers", "synthetic-estrogens", "tertiary-alcohols"] description: "Pharmaceutical drug" topic_path: "general/ethynyl-compounds" source: "https://en.wikipedia.org/wiki/Quinestrol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Pharmaceutical drug ::

| Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 464378599 | IUPAC_name = (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 | image = Quinestrol.svg | image_class = skin-invert-image | width = 250px | image2 = Quinestrol molecule ball.png | image_class2 = bg-transparent | width2 = 250px

| tradename = Estrovis, others | Drugs.com = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth | class = Estrogen; Estrogen ether

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = 120 hours (5 days) | excretion =

| CAS_number_Ref = | CAS_number = 152-43-2 | ATC_prefix = None | ATC_suffix = | PubChem = 9046 | IUPHAR_ligand = 7097 | DrugBank_Ref = | DrugBank = DB04575 | ChemSpiderID_Ref = | ChemSpiderID = 8694 | UNII_Ref = | UNII = JR0N7XD5GZ | KEGG_Ref = | KEGG = D00576 | ChEBI_Ref = | ChEBI = 8716 | ChEMBL_Ref = | ChEMBL = 1201165 | synonyms = Quinoestrol; Quinestrenol; Quinoestrenol; Ethinylestradiol 3-cyclopentyl ether; EECPE; EE2CPE; W-3566; 3-(Cyclopentyloxy)-17α-ethynylestra-1,3,5(10)-trien-17β-ol

| C=25 | H=32 | O=2 | SMILES = O(c1ccc2c(c1)CC[C@H]3[C@@H]4CCC@(O)[C@@]4(C)CC[C@H]23)C5CCCC5 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = PWZUUYSISTUNDW-VAFBSOEGSA-N

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. 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. On its own as an estrogen, quinestrol was taken once per week by mouth. As a combined birth control pill, it was used together with quingestanol acetate and was taken once per month by mouth.

Pharmacology

::figure[src="https://upload.wikimedia.org/wikipedia/commons/6/6d/Ethinylestradiol.svg" caption="active form]] of quinestrol."] ::

Quinestrol is a prodrug of ethinylestradiol (EE), with no estrogenic activity of its own. 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. Because of its much longer half-life, quinestrol is two to three times as potent as EE. 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.

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.

Society and culture

Generic names

Quinestrol is the generic name of the drug and its , , and . 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. 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.

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

References

References

  1. (1 January 1988). "Dictionary of Obstetrics and Gynecology". Walter de Gruyter.
  2. (2 December 2012). "The Breast: Morphology, Physiology, and Lactation". Elsevier Science.
  3. (6 December 2012). "The Menopause". Springer Science & Business Media.
  4. (6 December 2012). "Ovarian Function and its Disorders: Diagnosis and Therapy". Springer Science & Business Media.
  5. (22 October 2013). "Human Fertility Control: Theory and Practice". Elsevier Science.
  6. (18 June 1974). "Chemical Contraception". Macmillan International Higher Education.
  7. (1967). "Prolonged menstrual response of patients with gonadal failure following quinestrol administration". International Journal of Fertility.
  8. (April 1969). "Prolonged oestrogenic activity in rats after single oral administration of ethinyloestradiol-3-cyclopentyl ether". The Journal of Pharmacy and Pharmacology.
  9. (6 December 2012). "Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen". Springer Science & Business Media.
  10. (1 June 1999). "Hormone Replacement Therapy". Springer Science & Business Media.
  11. (January 1982). "Current status of estrogen therapy for the menopause". Fertility and Sterility.
  12. (1967). "Medical Gynaecology and Sociology". Medical and Scientific Services Limited.
  13. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
  14. (January 2000). "Index Nominum 2000: International Drug Directory". Taylor & Francis.
  15. (6 December 2012). "Concise Dictionary of Pharmacological Agents: Properties and Synonyms". Springer Science & Business Media.
  16. "Quinestrol". Drugs.com.
  17. "悦可婷 左炔诺孕酮炔雌醚片 6片/盒".
  18. (January 2012). "Combined effects of levonorgestrel and quinestrol on reproductive hormone levels and receptor expression in females of the Mongolian gerbil (Meriones unguiculatus)". Zoological Science.
  19. (September 2013). "Effects of levonorgestrel-quinestrol (EP-1) treatment on Mongolian gerbil wild populations: a case study". Integrative Zoology.

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ethynyl-compoundsantigonadotropinscyclopentyl-ethersestranesestrogen-etherssynthetic-estrogenstertiary-alcohols