Oxogestone phenpropionate

Oxogestone phenpropionate
Clinical data
Other names	Oxogesterone phenpropionate; Xinogestone; Oxageston; 20β-Hydroxy-19-norprogesterone phenylpropionate; 20β-Dihydro-19-norprogesterone 20β-(3-phenylpropionate); 20β-Hydroxy-19-norpregn-4-en-3-one 20β-(3-phenylpropionate); (20R)-3-Oxo-19-norpregn-4-en-20-yl 3-phenylpropanoate
Routes of; administration	intramuscular injection
Drug class	Progestogen; Progestogen ester
Identifiers
	IUPAC name [(1R)-1-[(8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl] 3-phenylpropanoate;
CAS Number	16915-80-3;
PubChem CID	20055360;
ChemSpider	16736681;
UNII	7IA4J676HM;
KEGG	D05308;
ChEMBL	ChEMBL2107303;
CompTox Dashboard (EPA)	DTXSID20937602 ;
Chemical and physical data
Formula	C29H38O3
Molar mass	434.620 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)OC(=O)CCC5=CC=CC=C5;
	InChI InChI=1S/C29H38O3/c1-19(32-28(31)15-8-20-6-4-3-5-7-20)26-13-14-27-25-11-9-21-18-22(30)10-12-23(21)24(25)16-17-29(26,27)2/h3-7,18-19,23-27H,8-17H2,1-2H3/t19-,23+,24-,25-,26-,27+,29-/m1/s1; Key:LHPBUFXEIOLURH-GQZONRFDSA-N;

Oxogestone phenpropionate (OPP; USANTooltip United States Adopted Name) (former developmental code name or tentative brand name Oxageston), also known as xinogestone, as well as 20β-hydroxy-19-norprogesterone 20β-(3-phenylpropionate), is a progestin related to the 19-norprogesterone derivatives which was developed as an injectable hormonal contraceptive, specifically a progestogen-only injectable contraceptive, in the 1960s and early 1970s but was never marketed. It was studied at a dose of 50 to 75 mg once a month by intramuscular injection but was associated with a high failure rate with this regimen and was not further developed. OPP is the 20β-(3-phenylpropionate) ester of oxogestone, which, similarly, was never marketed.

Parenteral potencies and durations of progestogens
Compound	Form	Dose for specific uses (mg)			DOA
Compound	Form	TFD	POICD	CICD	DOA
Algestone acetophenide	Oil soln.	–	–	75–150	14–32 d
Gestonorone caproate	Oil soln.	25–50	–	–	8–13 d
Hydroxyprogest. acetate	Aq. susp.	350	–	–	9–16 d
Hydroxyprogest. caproate	Oil soln.	250–500	–	250–500	5–21 d
Medroxyprog. acetate	Aq. susp.	50–100	150	25	14–50+ d
Megestrol acetate	Aq. susp.	–	–	25	>14 d
Norethisterone enanthate	Oil soln.	100–200	200	50	11–52 d
Progesterone	Oil soln.	200	–	–	2–6 d
	Aq. soln.	?	–	–	1–2 d
	Aq. susp.	50–200	–	–	7–14 d
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