Allylestrenol

Allylestrenol
Clinical data

Trade names	Gestanin, Gestanol, Gestanon, Gestin, Gestormone, Gestrenol, Maintaine Tab., Orageston, Premaston, Profar, Turinal
Pregnancy category	Used in threatened miscarriage and recurrent pregnancy loss
ATC code	G03DC01 (WHO)
Identifiers
IUPAC name (17β)-17-(prop-2-en-1-yl)estr-4-en-17-ol
Synonyms	Allyloestrenol; Allyl estrenol; Allyl oestrenol; 17α-Allylestr-4-en-17β-ol; SC-6393
CAS Number	432-60-0^Y
PubChem (CID)	235905
DrugBank	DB01431^Y
ChemSpider	205855^Y
UNII	I47VB5DZ8O^Y
KEGG	D01374^Y
ChEMBL	CHEMBL1445549^N
ECHA InfoCard	100.006.440
Chemical and physical data
Formula	C₂₁H₃₂O
Molar mass	300.48 g/mol
3D model (Jmol)	Interactive image
SMILES O[C@]2(CC[C@H]1[C@H]4[C@H](CC[C@@]12C)[C@@H]3\C(=C/CCC3)CC4)C\C=C
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
^NY (what is this?)

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, is a steroidal progestin of the 19-nortestosterone and 17α-allyltestosterone groups that is used to prevent threatened miscarriage, recurrent pregnancy loss and premature labor. It has also been studied as a treatment for benign prostatic hyperplasia in men, with encouraging results. 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.

Although it is less potent as a progestogen relative to many other 19-nortestosterone derivatives, 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. 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). It was patented in 1958 and has been marketed since 1961.

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