Fenestrel

Last updated
Fenestrel
Fenestrel.svg
Clinical data
Other namesDemethoxycarbestrol; NSC-86465; 2-methyl-3-ethyl-4-phenyl-δ4-cyclohexenecarboxylic acid
ATC code
  • None
Identifiers
  • 5-Ethyl-6-methyl-4-phenylcyclohex-3-ene-1-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C16H20O2
Molar mass 244.334 g·mol−1
3D model (JSmol)
  • CCC1C(C(CC=C1C2=CC=CC=C2)C(=O)O)C
  • InChI=1S/C16H20O2/c1-3-13-11(2)14(16(17)18)9-10-15(13)12-7-5-4-6-8-12/h4-8,10-11,13-14H,3,9H2,1-2H3,(H,17,18)
  • Key:CLMFEXDZPBGYQQ-UHFFFAOYSA-N

Fenestrel (INN, USAN) (developmental code name ORF-3858) is a synthetic, nonsteroidal estrogen that was developed as a postcoital contraceptive in the 1960s but was never marketed. [1] [2] [3] [4] Synthesized by Ortho Pharmaceutical in 1961 and studied extensively, it was coined the "morning-after-pill" or "postcoital antifertility agent". [5] Fenestrel is a seco analogue of doisynolic acid, and a member of the cyclohexenecarboxylic acid series of estrogens. [6] [7]

See also

Related Research Articles

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

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

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<span class="mw-page-title-main">Lynestrenol</span> Androgen and anabolic steroid

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

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

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

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

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

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

Norgesterone, also known as norvinodrel or vinylestrenolone and sold under the brand name Vestalin, is a progestin medication which was formerly used in birth control pills for women but is now no longer marketed. It was used in combination with the estrogen ethinylestradiol. It is taken by mouth.

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

Carbestrol is a synthetic, nonsteroidal estrogen of the cyclohexenecarboxylic acid group and seco analogue of doisynolic acid that was described in the literature in 1956 and developed for the treatment of prostate cancer in the 1960s but was never marketed.

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

Anordrin, also known as 2α,17α-diethynyl-A-nor-5α-androstane-2β,17β-diol dipropionate, is a synthetic, steroidal selective estrogen receptor modulator (SERM) which is used in China as an emergency contraceptive. It is the most commonly used emergency contraceptive in China. The drug is marketed in a combination formulation with mifepristone under the brand name Zi Yun. Anordrin has not been studied for use or marketed outside of China. It has been used in China since the 1970s.

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

Doisynolic acid is a synthetic, orally active, nonsteroidal estrogen that was never marketed. The reaction of estradiol or estrone with potassium hydroxide, a strong base, results in doisynolic acid as a degradation product, which retains high estrogenic activity, and this reaction was how the drug was discovered, in the late 1930s. The drug is a highly active and potent estrogen by the oral or subcutaneous route. The reaction of equilenin or dihydroequilenin with potassium hydroxide was also found to produce bisdehydrodoisynolic acid, whose levorotatory isomer is an estrogen with an "astonishingly" high degree of potency, while the dextrorotatory isomer is inactive. Doisynolic acid was named after Edward Adelbert Doisy, a pioneer in the field of estrogen research and one of the discoverers of estrone.

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

Doisynoestrol, also known as fenocycline, as well as cis-bisdehydrodoisynolic acid 7-methyl ether, is a synthetic nonsteroidal estrogen of the doisynolic acid group that is no longer marketed. It is a methyl ether of bisdehydrodoisynolic acid. Doisynoestrol was described in the literature in 1945. It has about 0.02% of the relative binding affinity of estradiol for the estrogen receptor.

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

Nisterime acetate (USAN) (developmental code name ORF-9326), also known as 2α-chloro-4,5α-dihydrotestosterone O-(p-nitrophenyl)oxime 17β-acetate or as 2α-chloro-5α-androstan-17β-ol-3-one O-(p-nitrophenyl)oxime 17β-acetate, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a derivative of dihydrotestosterone (DHT) that was developed as a postcoital contraceptive but was never marketed. It is an androgen ester – specifically, the C17α acetate ester of nisterime. Unlike antiprogestogens like mifepristone, nisterime acetate does not prevent implantation and instead induces embryo resorption as well as interrupts the post-implantation stage of pregnancy.

References

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  4. Kunjappu MJ (June 2011). "Pioneering studies of the "morning-after" pill". The Yale Journal of Biology and Medicine. 84 (2): 109–111. PMC   3117403 . PMID   21698041.
  5. Hahn DW, McGuire JL (6 December 2012). "The Use of Pharmacological Agents to Study Implantation". In Glasser SR, Bullock DW (eds.). Cellular and Molecular Aspects of Implantation. Springer Science & Business Media. pp. 478–. ISBN   978-1-4613-3180-3.
  6. Kirk RE, Othmer DF (1980). Encyclopedia of chemical technology. Wiley. p. 672. ISBN   978-0-471-02065-3.
  7. Acta europaea fertilitatis. Piccin Medical Books. 1969.