Hydroxyprogesterone heptanoate

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Not to be confused with 17α-Hydroxyprogesterone, Hydroxyprogesterone acetate, or Hydroxyprogesterone caproate.
Hydroxyprogesterone heptanoate
Clinical data
Trade namesH.O.P, Lutogil A.P., Lutogyl A.P., others
Other namesOHPH; Hydroxyprogesterone enanthate; OHPE; 17α-Hydroxyprogesterone heptanoate; 17α-Hydroxyprogesterone heptylate; 17α-Hydroxypregn-4-ene-3,20-dione 17α-heptanoate; 17α-Heptyloylpregn-4-ene-3,20-dione
Routes of
administration		Intramuscular injection
Drug classProgestin; Progestogen; Progestogen ester
ATC code
Identifiers
  • [(8R,9S,10R,13S,14S,17R)-17-Acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] heptanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.022.724 Edit this at Wikidata
Chemical and physical data
FormulaC28H42O4
Molar mass442.631 g/mol g·mol−1
3D model (JSmol)
  • CCCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(=O)C
  • InChI=1S/C28H42O4/c1-5-6-7-8-9-25(31)32-28(19(2)29)17-14-24-22-11-10-20-18-21(30)12-15-26(20,3)23(22)13-16-27(24,28)4/h18,22-24H,5-17H2,1-4H3/t22-,23+,24+,26+,27+,28+/m1/s1
  • Key:NKJYZYWCGKSMSV-BDPSOKNUSA-N

Hydroxyprogesterone heptanoate (OHPH), sold under the brand names H.O.P., Lutogil A.P., and Lutogyl A.P. among others, is a progestin medication which was developed by Roussel and Théramex and has been used clinically in France and Monaco but is no longer marketed.[1][2][3][4] It was a component of the experimental preparation Trophoboline (or Trophobolene), which also contained nandrolone decanoate and estrapronicate.[5][6][7] The medication was also studied or used in Tocogestan, a combination of hydroxyprogesterone heptanoate (200 mg), progesterone (50 mg), and tocopherol (250 mg) oil for intramuscular injection.[8][4][9] OHPH has been marketed since at least 1957, in combination preparations such as Triormon Depositum (estradiol dibutyrate, testosterone caproate, and OHPH) and Trioestrine Retard (estradiol diundecylate, testosterone cyclohexylpropionate, and OHPH).[10][11]

Pharmacology

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: [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30]
  2. ^ All given by intramuscular or subcutaneous injection.
  3. ^ 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. ^ 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. ^ a b In divided doses (2 × 125 or 250 mg for OHPC, 10 × 20 mg for P4).

Chemistry

See also: List of progestogens, Progestogen ester, and List of progestogen esters

OHPH, also known as hydroxyprogesterone enanthate (OHPE),[31] as well as 17α-hydroxyprogesterone heptanoate or 17α-hydroxypregn-4-ene-3,20-dione 17α-heptanoate, is a synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone.[1][2] It is a progestogen ester; specifically, it is the C17α heptanoate (enanthate) ester of 17α-hydroxyprogesterone.[1][2] Analogues of OHPH include hydroxyprogesterone acetate and hydroxyprogesterone caproate.[1][2]

References

  1. ^ a b c d J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 665–. ISBN 978-1-4757-2085-3.
  2. ^ a b c d Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 532–. ISBN 978-3-88763-075-1.
  3. ^ Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 612–. ISBN 978-3-7692-2114-5.
  4. ^ a b Axel Kleemann; Jürgen Engel (2001). Pharmaceutical Substances: Syntheses, Patents, Applications. Thieme. p. 1033. ISBN 978-3-13-558404-1.
  5. ^ Excerpta medica. Section 8, Neurology and neurosurgery. 1981. p. 10.
  6. ^ Testosterone Congeners—Advances in Research and Application: 2013 Edition: ScholarlyBrief. ScholarlyEditions. 21 June 2013. pp. 137–. ISBN 978-1-4816-9288-5.
  7. ^ Alberto Frigerio (1981). Chromatography in Biochemistry, Medicine and Environmental Research: Proceedings of the ... International Symposium on Chromatography in Biochemistry, Medicine and Environmental Research. Elsevier Scientific Publishing Company. p. 99.
  8. ^ https://www.google.com/patents/US6774122
  9. ^ http://content.iospress.com/articles/international-journal-of-risk-and-safety-in-medicine/jrs132
  10. ^ Ermiglia, G; Valli, P (1957). "Triormon depositum in climacteric syndrome. Curves of excretion of catabolites and duration of the therapeutic effect". Quaderni clin. ostet. e ginecol. 12: 284–93. Triormon depositum (estradiol dibutyrate 3, testosterone caprylate 50, and hydroxyprogesterone heptanoate 30 mg.), administered in castor oil-benzyl benzoate soln. or polyvinylpyrrolidone suspension to 21 women in climacteric, was followed by estradiol, pregnanediol, and 17-keto steroid urinary curves, most with a peak at the 4th day, and approaching starting values at the 8-10th day. The therapeutic efficacy of the drug was satisfactory.
  11. ^ Bordier, Philippe (1963). "Cure of fifteen osteoporosis cases by a delayed effect of hormonal association". Semaine des Hopitaux. 39 (2): 81–4. ISSN 0037-1777. The patients (females) received intramuscularly, every 10 days for 2-3 months, estradiol diundecyleate 2.25, testosterone cyclohexylpropionate 67.5, and hydroxyprogesterone heptylate 100 mg. ("trioestrine retard"). Their av. calcuria decreased 30.5% (0-69%) and asthenia, anorexia, and muscular activity improved.
  12. ^ Knörr K, Beller FK, Lauritzen C (17 April 2013). Lehrbuch der Gynäkologie. Springer-Verlag. pp. 214–. ISBN 978-3-662-00942-0.
  13. ^ Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C (8 March 2013). Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion. Springer-Verlag. pp. 583–. ISBN 978-3-642-95583-9.
  14. ^ Labhart A (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 554–. ISBN 978-3-642-96158-8.
  15. ^ 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. ISBN 978-94-009-8195-9.
  16. ^ Ufer J (1969). The Principles and Practice of Hormone Therapy in Gynaecology and Obstetrics. de Gruyter. p. 49. ISBN 9783110006148. 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.
  17. ^ Pschyrembel W (1968). Praktische Gynäkologie: für Studierende und Ärzte. Walter de Gruyter. pp. 598, 601. ISBN 978-3-11-150424-7.
  18. ^ Ferin 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. ISBN 978-0080168128. OCLC 278011135.
  19. ^ 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. ISBN 978-0-8247-8291-7.
  20. ^ Brotherton J (1976). Sex Hormone Pharmacology. Academic Press. p. 114. ISBN 978-0-12-137250-7.
  21. ^ 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. PMID 8013220.
  22. ^ Toppozada MK (April 1994). "Existing once-a-month combined injectable contraceptives". Contraception. 49 (4): 293–301. doi:10.1016/0010-7824(94)90029-9. PMID 8013216.
  23. ^ 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. ISBN 978-1-4613-2241-2.
  24. ^ 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. PMID 6452729.
  25. ^ 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. PMID 6223851.
  26. ^ Wright JC, Burgess DJ (29 January 2012). Long Acting Injections and Implants. Springer Science & Business Media. pp. 114–. ISBN 978-1-4614-0554-2.
  27. ^ 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.
  28. ^ Runnebaum BC, Rabe T, Kiesel L (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 429–. ISBN 978-3-642-73790-9.
  29. ^ Artini PG, Genazzani AR, Petraglia F (11 December 2001). Advances in Gynecological Endocrinology. CRC Press. pp. 105–. ISBN 978-1-84214-071-0.
  30. ^ King TL, Brucker MC, Kriebs JM, Fahey JO (21 October 2013). Varney's Midwifery. Jones & Bartlett Publishers. pp. 495–. ISBN 978-1-284-02542-2.
  31. ^ Batres, E.; Gomez, R.; Rosenkranz, G.; Sondheimer, F. (1956). "Notes - Steroids. LXXVI. Synthesis of Long Chain Carboxylic Acid Esters of 17α-Hydroxyprogesterone". The Journal of Organic Chemistry. 21 (2): 240–241. doi:10.1021/jo01108a601. ISSN 0022-3263.



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