Gestronol

Gestronol (BANTooltip British Approved Name), also known as gestonorone, as well as 17α-hydroxy-19-norprogesterone or 17α-hydroxy-19-norpregn-4-ene-3,20-dione, is a progestin of the 19-norprogesterone and 17α-hydroxyprogesterone groups which was never marketed.^[1][2][3] The C17α caproate ester of gestronol, gestonorone caproate (gestronol hexanoate), in contrast, has been marketed.^[1][2][3]

Other namesGestonorone; 17α-Hydroxy-19-norprogesterone; 17α-Hydroxy-19-norpregn-4-ene-3,20-dione

CAS Number

• 2137-18-0

PubChem CID

• 102210

ChemSpider

• 4386807

Quick facts Clinical data, Other names ...

Gestronol

Clinical data
Other names	Gestonorone; 17α-Hydroxy-19-norprogesterone; 17α-Hydroxy-19-norpregn-4-ene-3,20-dione
Identifiers
IUPAC name (8R,9S,10R,13S,14S,17R)-17-Acetyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number	2137-18-0
PubChem CID	102210
ChemSpider	4386807
UNII	H4G605B7VP
CompTox Dashboard (EPA)	DTXSID50175631
ECHA InfoCard	100.016.708
Chemical and physical data
Formula	C20H28O3
Molar mass	316.441 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)O
InChI InChI=1S/C20H28O3/c1-12(21)20(23)10-8-18-17-5-3-13-11-14(22)4-6-15(13)16(17)7-9-19(18,20)2/h11,15-18,23H,3-10H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1 Key:GTFUITFQDGVJSK-XGXHKTLJSA-N

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Gestronol shows relatively low affinity for the progesterone receptor, only about 12.5% of that of progesterone and about 2.5% of that of 19-norprogesterone in one assay.^[4] On the other hand, gestronol had far higher affinity than 17α-hydroxyprogesterone, which showed less than 0.1% of the affinity of progesterone for the progesterone receptor.^[4]