Allylestrenol

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Allylestrenol
Allylestrenol.svg
Clinical data
Trade names Gestanin, Gestanol, Gestanon, Gestin, Gestormone, Gestrenol, Maintaine Tab., Orageston, Premaston, Profar, Turinal[1][2][3]
Pregnancy
category
  • Used in threatened miscarriage and recurrent pregnancy loss
ATC code
Identifiers
Synonyms Allyloestrenol; Allyl estrenol; Allyl oestrenol; 17α-Allylestr-4-en-17β-ol; SC-6393[2]
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.006.440
Chemical and physical data
Formula C21H32O
Molar mass 300.48 g/mol
3D model (Jmol)
 NYesY (what is this?)  (verify)

Allylestrenol (INN) (brand names Gestanon, Gestanin, Orageston, Turinal, Gestin, others), or allyloestrenol (BAN), also known as 17α-allylestr-4-en-17β-ol or as 3-deketo-17α-allyl-19-nortestosterone,[4] is a steroidal progestin of the 19-nortestosterone and 17α-allyltestosterone groups[5][6][7] that is used to prevent threatened miscarriage, recurrent pregnancy loss and premature labor.[1][2][3][8] It has also been studied as a treatment for benign prostatic hyperplasia in men, with encouraging results.[9][10] Allylestrenol is marketed widely throughout Europe, including in the United Kingdom (no longer available), Russia, and many other European countries, and is also available in Japan, Hong Kong, India, Bangladesh, Indonesia, and much of Southeast Asia, though notably not in the United States or Canada.[1][3][11][12]

Although it is less potent as a progestogen relative to many other 19-nortestosterone derivatives,[13] allylestrenol is said to be virtually devoid of androgenic, estrogenic, or glucocorticoid activity, and hence, unlike virtually all other 19-nortestosterone derivatives, appears to be a pure progestogen with similar effects to those of progesterone.[6][14] As it is lacking in a keto group at the C3 position, allylestrenol is thought to be a prodrug into 17α-allyl-19-nortestosterone (or 17α-allylnandrolone).[15][7] It was patented in 1958[4] and has been marketed since 1961.[16][17][18]

See also[edit]

References[edit]

  1. ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 29–. ISBN 978-3-88763-075-1. 
  2. ^ a b c J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 31–. ISBN 978-1-4757-2085-3. 
  3. ^ a b c Sweetman, Sean C., ed. (2009). "Sex hormones and their modulators". Martindale: the complete drug reference (36th ed.). London: Pharmaceutical Press. p. 2082. ISBN 978-0-85369-840-1. 
  4. ^ a b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 170–. ISBN 978-0-8155-1856-3. 
  5. ^ Jeffrey K. Aronson (21 February 2009). Meyler's Side Effects of Endocrine and Metabolic Drugs. Elsevier. pp. 289–. ISBN 978-0-08-093292-7. 
  6. ^ a b Bergink, E.W.; Loonen, P.B.A.; Kloosterboer, H.J. (1985). "Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties". Journal of Steroid Biochemistry. 23 (2): 165–168. doi:10.1016/0022-4731(85)90232-8. ISSN 0022-4731. PMID 3928974. 
  7. ^ a b F. J. Zeelen (1990). Medicinal chemistry of steroids. Elsevier Science Limited. pp. 108–109. ISBN 978-0-444-88727-6. Other examples are allylestrenol (42), a pro-drug converted to the 3-keto analogue (43), which is used in the treatment of threatened abortion [78,79] and altrenogest (44), used in sows and mares to suppress ovulation and estrus behaviour [80]. [...] Progestins with a 17a-allyl side chain: (42) allylestrenol, (43), (44) altrenogest. 
  8. ^ Cortés-Prieto J, Bosch AO, Rocha JA (1980). "Allylestrenol: three years of experience with Gestanon in threatened abortion and premature labor". Clinical Therapeutics. 3 (3): 200–8. PMID 7459930. 
  9. ^ Fukuoka H, Ishibashi Y, Shiba T, Tuchiya F, Sakanishi S (July 1993). "[Clinical study of allylestrenol (Perselin) on patients with prostatic hypertrophy]". Hinyokika Kiyo. Acta Urologica Japonica (in Japanese). 39 (7): 679–83. PMID 7689782. 
  10. ^ Noguchi K, Takeda M, Hosaka M, Kubota Y (May 2002). "[Clinical effects of allylestrenol on patients with benign prostatic hyperplasia (BPH) evaluated with criteria for treatment efficacy in BPH]". Hinyokika Kiyo. Acta Urologica Japonica (in Japanese). 48 (5): 269–73. PMID 12094708. 
  11. ^ Wilt, Timothy J.; MacDONALD, RODERICK; Nelson, David (2002). "TAMSULOSIN FOR TREATING LOWER URINARY TRACT SYMPTOMS COMPATIBLE WITH BENIGN PROSTATIC OBSTRUCTION: A SYSTEMATIC REVIEW OF EFFICACY AND ADVERSE EFFECTS". The Journal of Urology. 167 (1): 177–183. doi:10.1016/S0022-5347(05)65407-9. ISSN 0022-5347. The 2 studies more than 13 weeks in duration compared tamsulosin with drugs not used in the United States for BPH, namely allyestrenol 24 and chlormadinone. 
  12. ^ https://www.drugs.com/international/allylestrenol.html
  13. ^ FIELD-RICHARDS S, SNAITH L (1961). "Allylestrenol: a new oral progestogen". Lancet. 1 (7169): 134–6. doi:10.1016/s0140-6736(61)91310-1. PMID 13699366. 
  14. ^ Madjerek, Z.; de Visser, J.; van der Vies, J.; Overbeek, G. A. (1960). "ALLYLESTRENOL, A PREGNANCY MAINTAINING ORAL GESTAGEN". European Journal of Endocrinology. XXXV (I): 8–19. doi:10.1530/acta.0.XXXV0008. ISSN 0804-4643. 
  15. ^ McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK (2008). "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". J. Steroid Biochem. Mol. Biol. 110 (1-2): 39–47. doi:10.1016/j.jsbmb.2007.10.008. PMID 18395441. 
  16. ^ Field-Richards, Sara; Snaith, Linton (1961). "ALLYLESTRENOL : A NEW ORAL PROGESTOGEN". The Lancet. 277 (7169): 134–136. doi:10.1016/S0140-6736(61)91310-1. ISSN 0140-6736. PMID 13699366. 
  17. ^ J. A. Simpson; E. S. C. Weiner (1997). Oxford English Dictionary Additions Series. Clarendon Press. pp. 36–. ISBN 978-0-19-860027-5. 1961 Lancet 21 Jan. 135/1 Allylestrenol ('Gestanin', Organon)..seems to be completely free from androgenic activity. 1962 Med. Jrnl. Austral. 8 Sept. 375/2 Each tablet of the combined hormone preparation, 'Premenquil', contains 5 mg. of allyloestrenol. [...] 
  18. ^ Medical Proceedings: A South African Journal for the Advancement of Medical Science. Juta and Company. 1962. Just released in South Africa is Gestanin, Organon Laboratories' new safe oral progestogen. Gestanin is allylestrenol, one of a new group of steroids synthesized by Organon. 

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