Hydroxyprogesterone heptanoate

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Hydroxyprogesterone heptanoate
Hydroxyprogesterone heptanoate.svg
Clinical data
Trade namesH.O.P, Lutogil A.P., Lutogyl A.P., others
SynonymsOHPH; 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
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.022.724 Edit this at Wikidata
Chemical and physical data
FormulaC28H42O4
Molar mass442.631 g/mol g·mol−1
3D model (JSmol)

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]

Chemistry[edit]

OHPH, also known as hydroxyprogesterone enanthate (OHPE),[12] 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[edit]

  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. ^ 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.