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Oxogestone phenpropionate

Chemical compound From Wikipedia, the free encyclopedia

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]

More information Compound, Form ...
Parenteral potencies and durations of progestogens[a][b]
Compound Form Dose for specific uses (mg)[c] DOA[d]
TFD[e] POICD[f] CICD[g]
Algestone acetophenideOil soln.––75–15014–32 d
Gestonorone caproateOil soln.25–50––8–13 d
Hydroxyprogest. acetate[h]Aq. susp.350––9–16 d
Hydroxyprogest. caproateOil soln.250–500[i]–250–5005–21 d
Medroxyprog. acetateAq. susp.50–1001502514–50+ d
Megestrol acetateAq. susp.––25>14 d
Norethisterone enanthateOil soln.100–2002005011–52 d
ProgesteroneOil soln.200[i]––2–6 d
Aq. soln.?––1–2 d
Aq. susp.50–200––7–14 d
Notes and sources:
  1. [a]
    Sources: [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26]
  2. [b]
    All given by intramuscular or subcutaneous injection.
  3. [c]
    Progesterone production during the luteal phase is ~25 (15–50) mg/day. The OIDTooltip ovulation-inhibiting dose of OHPC is 250 to 500 mg/month.
  4. [d]
    Duration of action in days.
  5. [e]
    Usually given for 14 days.
  6. [f]
    Usually dosed every two to three months.
  7. [g]
    Usually dosed once monthly.
  8. [h]
    Never marketed or approved by this route.
  9. [i]
    In divided doses (2 × 125 or 250 mg for OHPC, 10 × 20 mg for P4).
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Other namesOxogesterone 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
administrationintramuscular injection
Drug classProgestogen; Progestogen ester
CAS Number
Quick facts Clinical data, Other names ...
Oxogestone phenpropionate
Clinical data
Other namesOxogesterone 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 classProgestogen; Progestogen ester
Identifiers
  • [(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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC29H38O3
Molar mass434.620 g·mol−1
3D model (JSmol)
  • CC(C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)OC(=O)CCC5=CC=CC=C5
  • 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
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