Quinestrol

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Quinestrol
ファイル:Quinestrol.svg
ファイル:Quinestrol molecule ball.png
Systematic (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
Clinical data
Trade names Estrovis, others
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat. ?
Legal status ?
Routes By mouth
Pharmacokinetic data
Half-life >120 hours (>5 days)[1]
Identifiers
CAS number 152-43-2 YesY
ATC code None
PubChem CID 9046
IUPHAR ligand 7097
DrugBank DB04575
ChemSpider 8694 YesY
UNII JR0N7XD5GZ YesY
KEGG D00576 YesY
ChEBI CHEBI:8716 YesY
ChEMBL CHEMBL1201165 YesY
Synonyms Quinoestrol; Quinestrenol; Quinoestrenol; Ethinylestradiol 3-cyclopentyl ether; EECPE; EE2CPE; W-3566; 3-(Cyclopentyloxy)-17α-ethynylestra-1,3,5(10)-trien-17β-ol
Chemical data
Formula C25H32O2 
 YesY (what is this?)  (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]

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

ファイル: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 RBATooltip Relative binding affinity (%)a REP (%)b
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 ?

テンプレート:Oral potencies of estrogens

Chemistry

Quinestrol, also known as ethinylestradiol 3-cyclopentyl ether (EE2CPE), is a synthetic estrane steroid and a derivative of estradiol.[12][13] It is an estrogen ether, specifically the C3 cyclopentyl ether of ethinylestradiol (17α-ethynylestradiol).[12][13] Closely related estrogens include mestranol (ethinylestradiol 3-methyl ether) and ethinylestradiol sulfonate (EES; Turisteron; ethinylestradiol 3-isopropylsulfonate).[12][13]

History

Quinestrol was developed and introduced for medical use in the 1960s.[14]

Society and culture

Generic names

Quinestrol is the generic name of the drug and its INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, and BANTooltip British Approved Name.[12][13][15][16] It is also known by its former developmental code name W-3566.[12][13][15][16]

Brand names

Quinestrol has been marketed under brand names including Agalacto-Quilea, Basaquines, Eston, Estrovis, Estrovister, Plestrovis, Qui-Lea, Soluna, and Yueketing, among others.[12][13][15][16]

Availability

Quinestrol was marketed as Estrovis in the United States by Parke-Davis and as Qui-Lea in Argentina,[13] 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.[16]

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 (Chinese: 悦可婷) and Àiyuè (Chinese: 艾悦). 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]

References

  1. ↑ 以下の位置に戻る: 1.0 1.1 Sitruk-Ware R (6 December 2012). "Pharmacology of Different Administration Routes-Oral vs Transdermal.". In Oettel M, Schillinger E (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Handbook of Experimental Pharmacology. Vol. 135 / 2. Springer Science & Business Media. pp. 248–. doi:10.1007/978-3-642-60107-1_14. ISBN 978-3-642-60107-1.
  2. ↑ 以下の位置に戻る: 2.0 2.1 2.2 Zink C (1 January 1988). "Quinestrol". Dictionary of Obstetrics and Gynecology. Walter de Gruyter. pp. 204–. ISBN 978-3-11-085727-6.
  3. ↑ 以下の位置に戻る: 3.0 3.1 3.2 3.3 3.4 3.5 3.6 3.7 Peterson CM, Udoff LC (1 June 1999). "Primary and secondary hypogonadism in women.". In Meikle AW (ed.). Hormone Replacement Therapy. Springer Science & Business Media. pp. 381–. ISBN 978-1-59259-700-0.
  4. ↑ 以下の位置に戻る: 4.0 4.1 4.2 Quirk Jr JG, Wendel Jr GD (6 December 2012). "Biologic effects of natural and synthetic estrogens.". In Buchsbaum HJ (ed.). The Menopause. Springer Science & Business Media. pp. 60–. ISBN 978-1-4612-5525-3.
  5. ↑ 以下の位置に戻る: 5.0 5.1 5.2 Horsky (6 December 2012). "Contraception". In Horsky J, Presl J (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 85, 358, 367. ISBN 978-94-009-8195-9.
  6. ↑ 以下の位置に戻る: 6.0 6.1 6.2 Hawkins DF, Elder MG (22 October 2013). "Other Hormal Contraception Procedures". Human Fertility Control: Theory and Practice. Elsevier Science. pp. 92–94. ISBN 978-1-4831-6361-1.
  7. ↑ 以下の位置に戻る: 7.0 7.1 7.2 Bennett JP (18 June 1974). Chemical Contraception. Macmillan International Higher Education. pp. 61–. ISBN 978-1-349-02287-8.
  8. ↑ Vorherr H (2 December 2012). The Breast: Morphology, Physiology, and Lactation. Elsevier Science. pp. 201–203. ISBN 978-0-323-15726-1.
  9. ↑ 以下の位置に戻る: 9.0 9.1 Epstein JA (1967). "Prolonged menstrual response of patients with gonadal failure following quinestrol administration". International Journal of Fertility. 12 (2): 181–186. PMID 6033895.
  10. ↑ 以下の位置に戻る: 10.0 10.1 Giannina T, Meli A (April 1969). "Prolonged oestrogenic activity in rats after single oral administration of ethinyloestradiol-3-cyclopentyl ether". The Journal of Pharmacy and Pharmacology. 21 (4): 271–272. doi:10.1111/j.2042-7158.1969.tb08247.x. PMID 4390151. S2CID 19407816.
  11. ↑ Hammond CB, Maxson WS (January 1982). "Current status of estrogen therapy for the menopause". Fertility and Sterility. 37 (1): 5–25. doi:10.1016/S0015-0282(16)45970-4. PMID 6277697.
  12. ↑ 以下の位置に戻る: 12.0 12.1 12.2 12.3 12.4 12.5 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 522–. ISBN 978-1-4757-2085-3.
  13. ↑ 以下の位置に戻る: 13.0 13.1 13.2 13.3 13.4 13.5 13.6 "Quinestrol". Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 905–. ISBN 978-3-88763-075-1.
  14. ↑ 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.
  15. ↑ 以下の位置に戻る: 15.0 15.1 15.2 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.
  16. ↑ 以下の位置に戻る: 16.0 16.1 16.2 16.3 16.4 16.5 "Quinestrol". Drugs.com. Archived from the original on 20 October 2015.
  17. ↑ "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.{{cite web}}: CS1 maint: unrecognized language (link)
  18. ↑ Lv X, Shi D (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. 29 (1): 37–42. doi:10.2108/zsj.29.37. PMID 22233494. S2CID 22347486.
  19. ↑ 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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