Allylestrenol

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. However, except in the case of proven progesterone deficiency, its use for such purposes is no longer recommended. It is also used in Japan to treat benign prostatic hyperplasia (BPH) in men. The medication is used alone and is not formulated in combination with an estrogen. It is taken by mouth.

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" (and low affinity for SHBGTooltip sex hormone-binding globulin)
MetabolismLiver (reduction, hydroxylation, conjugation; CYP3A4)
Metabolites• 17α-Allyl-19-NTTooltip 17α-Allyl-19-nortestosterone
Elimination half-life"Several hours" or 10 hours
ExcretionUrine (as conjugates)
Identifiers
  • (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=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)

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

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

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