Hydroxyprogesterone heptanoate
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Clinical data | |
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Trade names | H.O.P, Lutogil A.P., Lutogyl A.P., others |
Synonyms | OHPH; 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 class | Progestin; Progestogen; Progestogen ester |
ATC code | |
Identifiers | |
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CAS Number |
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PubChem CID | |
ChemSpider | |
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ECHA InfoCard |
100.022.724 |
Chemical and physical data | |
Formula | C28H42O4 |
Molar mass | 442.631 g/mol |
3D model (JSmol) | |
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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
Progestogen | Type | Class | TFD (14 days) | MDT (week) | OID (month) | POIC-D (2–3 months) | CIC-D (month) | Duration |
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Algestone acetophenide | Synthetic | Pregnane | ND | ND | ND | NA | 75–150 mg | ND |
Gestonorone caproate | Synthetic | Norpregnane | ND | ND | ND | NA | NA | ND |
Hydroxyprogesterone caproate | Synthetic | Pregnane | 250–500 mg | 25 mg | 250–500 mg | NA | 250–500 mg | 250 mg ≈ 10 days |
Medroxyprogesterone acetate | Synthetic | Pregnane | 50–100 mg | ND | ND | 150 mg | 25 mg | 50 mg ≈ 14 days |
Megestrol acetate | Synthetic | Pregnane | ND | ND | ND | NA | 25 mg | ND |
Norethisterone enanthate | Synthetic | Estrane | ND | ND | ND | 200 mg | 50 mg | ND |
Progesterone (oil soln.) | Bioidentical | Pregnane | 200 mg | ND | ND | NA | NA | 25 mg ≈ 2–3 days |
Progesterone (cryst. susp.) | Bioidentical | Pregnane | 50–100 mg | ND | ND | NA | NA | 50 mg ≈ 14 days |
Notes: All by intramuscular injection. Abbreviations: TFD = Endometrial transformation dose. MDT = Menstrual delay test dose (Greenblatt). OID = Ovulation-inhibiting dose (antigonadotropic effect; without an estrogen). POIC-D = Progestogen-only injectable contraceptive dose(s). CIC-D = Combined injectable contraceptive dose(s). Miscellaneous: Direct link to table. Sources:[12][13][14][15][16] |
Chemistry
OHPH, also known as hydroxyprogesterone enanthate (OHPE),[17] 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 2 3 4 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.
- 1 2 3 4 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 532–. ISBN 978-3-88763-075-1.
- ↑ Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 612–. ISBN 978-3-7692-2114-5.
- 1 2 Axel Kleemann; Jürgen Engel (2001). Pharmaceutical Substances: Syntheses, Patents, Applications. Thieme. p. 1033. ISBN 978-3-13-558404-1.
- ↑ Excerpta medica. Section 8, Neurology and neurosurgery. 1981. p. 10.
- ↑ Testosterone Congeners—Advances in Research and Application: 2013 Edition: ScholarlyBrief. ScholarlyEditions. 21 June 2013. pp. 137–. ISBN 978-1-4816-9288-5.
- ↑ 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.
- ↑ https://www.google.com/patents/US6774122
- ↑ http://content.iospress.com/articles/international-journal-of-risk-and-safety-in-medicine/jrs132
- ↑ 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.
- ↑ 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.
- ↑ Karl Knörr; Fritz K. Beller; Christian Lauritzen (17 April 2013). Lehrbuch der Gynäkologie. Springer-Verlag. pp. 214–. ISBN 978-3-662-00942-0.
- ↑ Karl Knörr; Henriette Knörr-Gärtner; Fritz K. Beller; Christian Lauritzen (8 March 2013). Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion. Springer-Verlag. pp. 583–. ISBN 978-3-642-95583-9.
- ↑ Sang GW (April 1994). "Pharmacodynamic effects of once-a-month combined injectable contraceptives". Contraception. 49 (4): 361–85. doi:10.1016/0010-7824(94)90033-7. PMID 8013220.
- ↑ 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.
- ↑ Bagade O, Pawar V, Patel R, Patel B, Awasarkar V, Diwate S (2014). "Increasing use of long-acting reversible contraception: safe, reliable, and cost-effective birth control" (PDF). World J Pharm Pharm Sci. 3 (10): 364–392. ISSN 2278-4357.
- ↑ 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.