Lynestrenol phenylpropionate

Chemical compound From Wikipedia, the free encyclopedia

Lynestrenol phenylpropionate (LPP), also known as ethynylestrenol phenylpropionate, is a progestin and a progestogen ester which was developed for potential use as a progestogen-only injectable contraceptive by Organon but was never marketed.[1][2][3][4][5][6][7][8] It was assessed at doses of 25 to 75 mg in an oil solution once a month by intramuscular injection.[1][4] LPP was associated with high contraceptive failure at the low dose and with poor cycle control.[3] The medication was found to produce estrogenic effects in the endometrium in women due to transformation into estrogenic metabolites.[4]

Other namesLPP; 17α-Ethynylestr-4-en-17β-ol 17β-(3-phenylpropionate); 19-Nor-17α-pregn-4-en-20-yn-17-ol benzenepropanoate
Routes of
administrationIntramuscular injection
Drug classProgestogen; Progestin; Progestogen ester
CAS Number
Quick facts Clinical data, Other names ...
Lynestrenol phenylpropionate
Clinical data
Other namesLPP; 17α-Ethynylestr-4-en-17β-ol 17β-(3-phenylpropionate); 19-Nor-17α-pregn-4-en-20-yn-17-ol benzenepropanoate
Routes of
administration		Intramuscular injection
Drug classProgestogen; Progestin; Progestogen ester
Identifiers
  • [(8R,9S,10R,13S,14S,17R)-17-Ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl] 3-phenylpropanoate
CAS Number
Chemical and physical data
FormulaC29H36O2
Molar mass416.605 g·mol−1
3D model (JSmol)
  • O(C(CCC1C=CC=CC=1)=O)[C@](C#C)1CC[C@]([H])2[C@@]([H])3CCC4=CCCC[C@]4([H])[C@@]3([H])CC[C@@]21C
  • InChI=1S/C29H36O2/c1-3-29(31-27(30)16-13-21-9-5-4-6-10-21)20-18-26-25-15-14-22-11-7-8-12-23(22)24(25)17-19-28(26,29)2/h1,4-6,9-11,23-26H,7-8,12-20H2,2H3/t23-,24+,25+,26-,28-,29-/m0/s1
  • Key:JOWUABYPVVAHHK-IISZJVLJSA-N
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A single intramuscular injection of 50 to 100 mg LPP in oil solution has been found to have a duration of action of 14 to 30 days in terms of clinical biological effect in the uterus and on body temperature in women.[9]

LPP has a long biological half-life in rats when given as an intramuscular depot injection; its half-life was similar to that of nandrolone laurate (nandrolone dodecanoate) and was about 2-fold longer than that of nandrolone decanoate, 10-fold longer than that of lynestrenol and nandrolone phenylpropionate, 50-fold longer than that of progesterone, and 430-fold longer than that of nandrolone.[5][6]

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: [10][11][12][13][14][15][9][16][17][18][19][20][21][22][23][24][25][26][27]
  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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References

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