Allenolic acid

Allenolic acid, or allenoic acid, is a synthetic,[1] nonsteroidal estrogen discovered in 1947 or 1948 that, although studied clinically,[2] was never marketed.[3][4][5] It is an open-ring or seco-analogue of steroidal estrogens like estrone and equilenin.[6][7][8] The compound was named after Dr. Edgar Allen, one of the pioneers in estrogen research.[9][10] Although described as an estrogen, allenolic acid probably is totally inactive at the receptor, whereas a derivative, allenestrol (α,α-dimethyl-β-ethylallenolic acid), is reported to be a potent estrogen.[11] Another derivative of allenolic acid (specifically 6-methoxy-allenestrol), methallenestril (brand name Vallestril), is also a potent estrogen and, in contrast to allenolic acid and allenestrol, has been marketed.[12][13][14][15]

Allenolic acid
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H12O3
Molar mass216.23258 g/mol g·mol−1
3D model (JSmol)

See also

References
  1. Rodolfo Paoletti; N. Pasetto; J.L. Ambrus (6 December 2012). The Menopause and Postmenopause: The Proceedings of an International Symposium held in Rome, June 1979. Springer Science & Business Media. pp. 110–. ISBN 978-94-011-7230-1.
  2. American Practitioner and Digest of Treatment. Lippincott. January 1951. p. 443.
  3. William J. Rea; Kalpana Patel (18 June 2010). Reversibility of Chronic Degenerative Disease and Hypersensitivity, Volume 1: Regulating Mechanisms of Chemical Sensitivity. CRC Press. pp. 464–. ISBN 978-1-4398-1345-4.
  4. Geynet, C.; Millet, C.; Truong, H.; Baulieu, E.E. (1972). "Estrogens and Antiestrogens". Gynecologic and Obstetric Investigation. 3 (1–4): 1–29. doi:10.1159/000301742. ISSN 1423-002X.
  5. Furuya, Hiroshi; Deguchi, Keiji; Shima, Motowo (1957). "Experimental and clinical studies on a new synthetic estrogen, an allenolic acid derivative, vallestril". American Journal of Obstetrics and Gynecology. 74 (3): 635–650. doi:10.1016/0002-9378(57)90519-7. ISSN 0002-9378.
  6. Indian Journal of Chemistry: Organic including medicinal. Council of Scientific & Industrial Research. 1980. p. 886.
  7. Paul Ghalioungui; Ahmed Ghareeb (1963). Endocrines, Vitamins, and Some Common Metabolic Disorders. Dar al-Maaref. p. 194.
  8. James D. Morrison (November 1983). Stereodifferentiating addition reactions. Academic Press. p. v. ISBN 978-0-12-507702-6.
  9. Willard Owen Thompson (1953). The Year Book of Endocrinology. Year Book Medical Publishers. p. 292.
  10. American Practitioner and Digest of Treatment. Lippincott. January 1956.
  11. Clark, Edward R.; Robson, R. D. (1959). "753. Oestrogenic carboxylic acids. Part II. Open-chain analogues of doisynolic acid". Journal of the Chemical Society (Resumed): 3714. doi:10.1039/jr9590003714. ISSN 0368-1769.
  12. Journal of the Japanese Obstetrical & Gynecological Society. 1958. p. 83.
  13. Erich Heftmann (1970). Steroid Biochemistry. Academic Press. p. 144.
  14. The Effects of the Sulfonylureas and Related Compounds in Experimental and Clinical Diabetes. The Academy. 1957. p. 681.
  15. Alan C. Sartorelli; David G. Johns (27 November 2013). Antineoplastic and Immunosuppressive Agents. Springer Science & Business Media. pp. 106–. ISBN 978-3-642-65806-8.


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