Allylestrenol

Allylestrenol
Clinical data
Trade namesGestanin, Gestanon, Perselin, Turinal, others
Other namesAllyloestrenol; SC-6393; Org AL-25; 3-Deketo-17α-allyl-19-nortestosterone; 17α-Allylestr-4-en-17β-ol; 17α-(Prop-2-en-1-yl)estr-4-en-17β-ol
Pregnancy
category
  • Used in threatened miscarriage and recurrent pregnancy loss
Routes of
administration		By mouth
Drug classProgestogen; Progestin
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding"Considerable"[1][2] (and low affinity for SHBGTooltip sex hormone-binding globulin)[3]
MetabolismLiver (reduction, hydroxylation, conjugation; CYP3A4)[1][2][5]
Metabolites• 17α-Allyl-19-NTTooltip 17α-Allyl-19-nortestosterone[3][1][2]
Elimination half-life"Several hours" or 10 hours[4][1][2]
ExcretionUrine (as conjugates)[1][2]
Identifiers
IUPAC name
  • (8R,9S,10R,13S,14S,17R)-13-methyl-17-prop-2-enyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.440
Chemical and physical data
FormulaC21H32O
Molar mass300.486 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(CC=C)O)CCC4=CCCC[C@H]34
InChI
  • InChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1 Y
  • Key:ATXHVCQZZJYMCF-XUDSTZEESA-N Y
  (verify)

Allylestrenol, sold under the brand names Gestanin and Turinal among others, is a progestin medication which is used to treat recurrent and threatened miscarriage and to prevent premature labor in pregnant women.[6][7][8] However, except in the case of proven progesterone deficiency, its use for such purposes is no longer recommended.[6] It is also used in Japan to treat benign prostatic hyperplasia (BPH) in men.[9][10][11] The medication is used alone and is not formulated in combination with an estrogen.[12] It is taken by mouth.[13]

Side effects of allylestrenol are few and have not been well-defined, but are assumed to be similar to those of related medications.[14] Allylestrenol is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[15] It has no other important hormonal activity.[3][16] The medication is a prodrug of 17α-allyl-19-nortestosterone (3-ketoallylestrenol) in the body.[17][18][3]

Allylestrenol was first described in 1958 and was introduced for medical use by 1961.[19][20][21][22] It has been marketed widely throughout the world in the past, but today its availability and usage are relatively limited.[23][6][24][25] It remains available in a few European countries and in a number of Asian countries.[23][6][24][25]

  1. ^ a b c d e Cite error: The named reference BengtssonTausk1972 was invoked but never defined (see the help page).
  2. ^ a b c d e Cite error: The named reference Thijssen1967 was invoked but never defined (see the help page).
  3. ^ a b c d Cite error: The named reference BerginkLoonen1985 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference SahaRoy2000 was invoked but never defined (see the help page).
  5. ^ "SuperCYP".
  6. ^ a b c d Sweetman SC, 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.
  7. ^ 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): 200–208. PMID 7459930.
  8. ^ Haas DM, Hathaway TJ, Ramsey PS (November 2019). "Progestogen for preventing miscarriage in women with recurrent miscarriage of unclear etiology". The Cochrane Database of Systematic Reviews. 2019 (11). doi:10.1002/14651858.CD003511.pub5. PMC 6953238. PMID 31745982.
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  10. ^ Cite error: The named reference pmid1722628 was invoked but never defined (see the help page).
  11. ^ Ishizuka O, Nishizawa O, Hirao Y, Ohshima S (November 2002). "Evidence-based meta-analysis of pharmacotherapy for benign prostatic hypertrophy". International Journal of Urology. 9 (11): 607–612. doi:10.1046/j.1442-2042.2002.00539.x. PMID 12534901.
  12. ^ Cite error: The named reference Muller1998 was invoked but never defined (see the help page).
  13. ^ Ganguly NK, Bano R, Seth SD (18 November 2009). "Drug Discovery and Development". In Seth SD, Seth V (eds.). Textbook Of Pharmacology. Elsevier India. pp. 1–. ISBN 978-81-312-1158-8.
  14. ^ Cite error: The named reference Borglin1960 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference pmid13699366 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Madjerekde Visser1960 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference pmid18395441 was invoked but never defined (see the help page).
  18. ^ Cite error: The named reference Zeelen1990 was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
  20. ^ Cite error: The named reference Field-RichardsSnaith1961 was invoked but never defined (see the help page).
  21. ^ Cite error: The named reference SimpsonWeiner1997 was invoked but never defined (see the help page).
  22. ^ Cite error: The named reference Juta1962 was invoked but never defined (see the help page).
  23. ^ a b Cite error: The named reference Micromedex was invoked but never defined (see the help page).
  24. ^ a b Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  25. ^ a b Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
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