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.^[1]^[2]^[3]^[4]^[5]^[6]^[7] 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.^[5] OPP is the 20β-(3-phenylpropionate) ester of oxogestone, which, similarly, was never marketed.^[1]

v
t
e
Parenteral potencies and durations of progestogens^[a]^[b]
Compound	Form	Dose for specific uses (mg)^[c]			DOA^[d]
Compound	Form	TFD^[e]	POICD^[f]	CICD^[g]	DOA^[d]
Algestone acetophenide	Oil soln.	-	–	75–150	14–32 d
Gestonorone caproate	Oil soln.	25–50	–	–	8–13 d
Hydroxyprogest. acetate^[h]	Aq. susp.	350	–	–	9–16 d
Hydroxyprogest. caproate	Oil soln.	250–500^[i]	–	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^[i]	–	–	2–6 d
	Aq. soln.	?	–	–	1–2 d
	Aq. susp.	50–200	–	–	7–14 d
Notes and sources:

References

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[2]

[3]

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[5]

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[7]

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[b]

[c]

[d]

[e]

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[g]

[h]

[i]

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Oxogestone phenpropionate

See also

References

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