Chemistry:Chloroethynylnorgestrel
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| Other names | Chloroethynyl norgestrel; WY-4355; 17α-Chloroethynyl-13β-ethylgon-4-en-17β-ol-3-one; 17α-Chloroethynyl-18-methylestr-4-en-17β-ol-3-one; 17α-Chloroethynyl-18-methyl-19-nortestosterone |
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| Formula | C21H27ClO2 |
| Molar mass | 346.90 g·mol−1 |
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Chloroethynylnorgestrel (developmental code name WY-4355) is a steroidal progestin of the 19-nortestosterone group related to norgestrel that was investigated as an oral contraceptive in the 1970s but was never marketed.[1][2][3][4]
In combination with mestranol, similarly to ethynerone and anagestone acetate (and certain other progestogens, including progesterone and several other 17α-hydroxyprogesterone derivatives), chloroethynylnorgestrel was found to produce striking mammary tumors in beagle dogs after administration at very high dosages (10- to 25-fold human clinical dosages) for prolonged periods of time.[1][3][4] This resulted in the discontinuation of its development, along with that of ethynerone and anagestone acetate, as well as the removal of several progestins, including chlormadinone acetate, medroxyprogesterone acetate, and megestrol acetate, from various markets as contraceptives (although medroxyprogesterone acetate has since been reintroduced).[1][5] Subsequent research revealed that the risk is species-dependent and unique to canines and that there is no similar risk for humans.[6]
References
- ↑ 1.0 1.1 1.2 Carcinogenic Hormones. Springer Science & Business Media. 6 December 2012. pp. 149–. ISBN 978-3-642-81267-5. https://books.google.com/books?id=lOLnCAAAQBAJ&pg=PA149.
- ↑ "The morphologic effects of synthetic reproductive steroids on the mammary gland of rhesus monkeys. Mestranol, ethynerone, mestranol-ethynerone, chloroethynyl norgestrel-mestranol, and anagestone acetate-mestranol combinations". The American Journal of Pathology 131 (2): 213–234. May 1988. PMID 3358452.
- ↑ 3.0 3.1 "FDA studies of estrogen, progestogens, and estrogen/progestogen combinations in the dog and monkey". Journal of Toxicology and Environmental Health 3 (1–2): 179–193. September 1977. doi:10.1080/15287397709529557. PMID 411941. Bibcode: 1977JTEH....3..179G.
- ↑ 4.0 4.1 "Mammary Neoplasia in Animals: Pathologic Aspects and the Effects of Contraceptive Steroids". Carcinogenic Hormones. 66. 1979. 129–160. doi:10.1007/978-3-642-81267-5_4. ISBN 978-3-540-08995-7.
- ↑ "Interspecies Extrapolation". Low Dose Exposures in the Environment: Dose-Effect Relations and Risk Evaluation. Springer Science & Business Media. 11 November 2013. pp. 135–. ISBN 978-3-662-08422-9. https://books.google.com/books?id=eiL4CAAAQBAJ&pg=PA135.
- ↑ "Development of progestogens.". Female Contraception: Update and Trends. Springer Science & Business Media. 6 December 2012. pp. 134–. ISBN 978-3-642-73790-9. https://books.google.com/books?id=LtT6CAAAQBAJ&pg=PA134.
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