Jump to content

Lynestrenol phenylpropionate

Add links
From Wikipedia, the free encyclopedia
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 mass416.605g·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

Lynestrenol phenylpropionate(LPP), also known asethynylestrenol phenylpropionate,is aprogestinand aprogestogen esterwhich was developed for potential use as aprogestogen-only injectable contraceptivebyOrganonbut was never marketed.[1][2][3][4][5][6][7][8]It was assessed at doses of 25 to 75 mg in anoil solutiononce a month byintramuscular 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 produceestrogeniceffects in theendometriumin women due totransformationinto estrogenicmetabolites.[4]

A singleintramuscular injectionof 50 to 100 mg LPP inoil solutionhas been found to have aduration of actionof 14 to 30 days in terms of clinicalbiological effectin theuterusand onbody temperaturein women.[9]

LPP has a longbiological half-lifein rats when given as an intramusculardepot injection;its half-life was similar to that ofnandrolone laurate(nandrolone dodecanoate) and was about 2-fold longer than that ofnandrolone decanoate,10-fold longer than that oflynestrenolandnandrolone phenylpropionate,50-fold longer than that ofprogesterone,and 430-fold longer than that ofnandrolone.[5][6]

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 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:
  1. ^Sources:[10][11][12][13][14][15][9][16][17][18][19][20][21][22][23][24][25][26][27]
  2. ^All given byintramuscularorsubcutaneous injection.
  3. ^Progesterone production during theluteal phaseis ~25 (15–50) mg/day. TheOIDTooltip ovulation-inhibiting doseof OHPC is 250 to 500 mg/month.
  4. ^Duration of action in days.
  5. ^Usually given for 14 days.
  6. ^Usually dosed every two to three months.
  7. ^Usually dosed once monthly.
  8. ^Never marketed or approved by this route.
  9. ^abIn divided doses (2 × 125 or 250 mg forOHPC,10 × 20 mg forP4).

See also

[edit]

References

[edit]
  1. ^abElsayed Saad Eldin Hafez (1980).Human reproduction: conception and contraception.Harper and Row. p. 607,614.ISBN978-0-06-141066-6.
  2. ^Mokhtar K. Toppozada (1983). "Monthly Injectable Contraceptives". In Alfredo Goldsmith; Mokhtar Toppozada (eds.).Long-Acting Contraception.pp. 93–103.OCLC35018604.
  3. ^abToppozada M (June 1977). "The clinical use of monthly injectable contraceptive preparations".Obstet Gynecol Surv.32(6): 335–47.doi:10.1097/00006254-197706000-00001.PMID865726.
  4. ^abcBadawy S, Makhlouf A (1975)."The contraceptive action of lynestrenol phenylpropionate".Adv Plan Parent.10(3): 149–53.PMID789155.
  5. ^abvan der Vies J (1985). "Implications of basic pharmacology in the therapy with esters of nandrolone".Acta Endocrinol Suppl (Copenh).271(3_Suppla): 38–44.doi:10.1530/acta.0.109S0038.PMID3865480.
  6. ^abVan der Vies, J (1969). "Mechanism of action of long-acting hormone preparations".Organorama.6(5): 4–8.ISSN0369-7762.Studies were made with nandrolone phenpropionate (Durabolin), nandrolone decanoate, and 16α-ethylprogesterone in peanut oil injected into the gastrocnemius muscle of rats. The free steroid was much more rapidly resorbed than the esters, explaining the action-prolonging effects obtained with the latter. Generally, resorption rates correlated well with duration of action. Resorption from the muscle was followed by transport to the receptor site in the body, during which time ester hydrolysis may occur, releasing the free steroid. Resorption and hydrolysis take place independently, since plasma with inactivated enzymes (heated to 55°) eluted the compds. from a filter paper strip as rapidly as did normal plasma.
  7. ^van der Vies J (August 1970). "Model studies in vitro with long-acting hormonal preparations".Acta Endocrinol.64(4): 656–69.doi:10.1530/acta.0.0640656.PMID5468664.
  8. ^Hobbelen PM, Coert A, Geelen JA, van der Vies J (January 1975). "Interactions of steroids with serum lipoproteins".Biochem. Pharmacol.24(2): 165–72.doi:10.1016/0006-2952(75)90273-7.PMID163092.
  9. ^abFerin J (September 1972)."Effects, Duration of Action and Metabolism in Man".In Tausk M (ed.).Pharmacology of the Endocrine System and Related Drugs: Progesterone, Progestational Drugs and Antifertility Agents.Vol. II. Pergamon Press. pp. 13–24.ISBN978-0080168128.OCLC278011135.
  10. ^Knörr K, Beller FK, Lauritzen C (17 April 2013).Lehrbuch der Gynäkologie.Springer-Verlag. pp. 214–.ISBN978-3-662-00942-0.
  11. ^Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C (8 March 2013).Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion.Springer-Verlag. pp. 583–.ISBN978-3-642-95583-9.
  12. ^Labhart A (6 December 2012).Clinical Endocrinology: Theory and Practice.Springer Science & Business Media. pp. 554–.ISBN978-3-642-96158-8.
  13. ^Horský J, Presl J (1981)."Hormonal Treatment of Disorders of the Menstrual Cycle".In Horsky J, Presl K (eds.).Ovarian Function and its Disorders: Diagnosis and Therapy.Springer Science & Business Media. pp. 309–332.doi:10.1007/978-94-009-8195-9_11.ISBN978-94-009-8195-9.
  14. ^Ufer J (1969).The Principles and Practice of Hormone Therapy in Gynaecology and Obstetrics.de Gruyter. p. 49.ISBN9783110006148.17α-Hydroxyprogesterone caproate is a depot progestogen which is entirely free of side actions. The dose required to induce secretory changes in primed endometrium is about 250 mg. per menstrual cycle.
  15. ^Pschyrembel W (1968).Praktische Gynäkologie: für Studierende und Ärzte.Walter de Gruyter. pp. 598, 601.ISBN978-3-11-150424-7.
  16. ^Henzl MR, Edwards JA (10 November 1999). "Pharmacology of Progestins: 17α-Hydroxyprogesterone Derivatives and Progestins of the First and Second Generation". In Sitruk-Ware R, Mishell DR (eds.).Progestins and Antiprogestins in Clinical Practice.Taylor & Francis. pp. 101–132.ISBN978-0-8247-8291-7.
  17. ^Brotherton J (1976).Sex Hormone Pharmacology.Academic Press. p. 114.ISBN978-0-12-137250-7.
  18. ^Sang GW (April 1994). "Pharmacodynamic effects of once-a-month combined injectable contraceptives".Contraception.49(4): 361–385.doi:10.1016/0010-7824(94)90033-7.PMID8013220.
  19. ^Toppozada MK (April 1994). "Existing once-a-month combined injectable contraceptives".Contraception.49(4): 293–301.doi:10.1016/0010-7824(94)90029-9.PMID8013216.
  20. ^Goebelsmann U (1986)."Pharmacokinetics of Contraceptive Steroids in Humans".In Gregoire AT, Blye RP (eds.).Contraceptive Steroids: Pharmacology and Safety.Springer Science & Business Media. pp. 67–111.doi:10.1007/978-1-4613-2241-2_4.ISBN978-1-4613-2241-2.
  21. ^Becker H, Düsterberg B, Klosterhalfen H (1980). "[Bioavailability of cyproterone acetate after oral and intramuscular application in men (author's transl)]" [Bioavailability of Cyproterone Acetate after Oral and Intramuscular Application in Men].Urologia Internationalis.35(6): 381–385.doi:10.1159/000280353.PMID6452729.
  22. ^Moltz L, Haase F, Schwartz U, Hammerstein J (May 1983). "[Treatment of virilized women with intramuscular administration of cyproterone acetate]" [Efficacy of Intra muscularly Applied Cyproterone Acetate in Hyperandrogenism].Geburtshilfe und Frauenheilkunde.43(5): 281–287.doi:10.1055/s-2008-1036893.PMID6223851.
  23. ^Wright JC, Burgess DJ (29 January 2012).Long Acting Injections and Implants.Springer Science & Business Media. pp. 114–.ISBN978-1-4614-0554-2.
  24. ^Chu YH, Li Q, Zhao ZF (April 1986)."Pharmacokinetics of megestrol acetate in women receiving IM injection of estradiol-megestrol long-acting injectable contraceptive".The Chinese Journal of Clinical Pharmacology.The results showed that after injection the concentration of plasma MA increased rapidly. The meantime of peak plasma MA level was 3rd day, there was a linear relationship between log of plasma MA concentration and time (day) after administration in all subjects, elimination phase half-life t1/2β = 14.35 ± 9.1 days.
  25. ^Runnebaum BC, Rabe T, Kiesel L (6 December 2012).Female Contraception: Update and Trends.Springer Science & Business Media. pp. 429–.ISBN978-3-642-73790-9.
  26. ^Artini PG, Genazzani AR, Petraglia F (11 December 2001).Advances in Gynecological Endocrinology.CRC Press. pp. 105–.ISBN978-1-84214-071-0.
  27. ^King TL, Brucker MC, Kriebs JM, Fahey JO (21 October 2013).Varney's Midwifery.Jones & Bartlett Publishers. pp. 495–.ISBN978-1-284-02542-2.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Lynestrenol_phenylpropionate&oldid=1184633834"