Hydroxyprogesterone heptanoate

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Not to be confused with 17α-Hydroxyprogesterone, Hydroxyprogesterone acetate, or Hydroxyprogesterone caproate.
Hydroxyprogesterone heptanoate
Progestin; 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
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), also known as hydroxyprogesterone enanthate (OHPE) and sold under the brand names H.O.P., Lutogil A.P., and Lutogyl A.P. among others, is a

Triormon Depositum).[4][5][6][7][8][9][10] OHPH is given by injection into muscle at regular intervals.[11][9]

OHPH is a progestin, or a

synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[12][13][14] It appears to have similar pharmacology to that of the closely related medication hydroxyprogesterone caproate (OHPC).[15][16][17]

OHPH was first described by 1954[16] and was introduced for medical use by 1957.[6] It has been used clinically in France and Monaco in the past but is no longer marketed.[2][3][4]

Medical uses

OHPH is a progestogen and was used in situations in which progestogens were indicated.[12][13][14]

Available forms

OHPH was provided as a 125 mg/1 mL

Trophobolene (or Trophoboline), which also contained estrapronicate (estradiol nicotinate propionate) and nandrolone undecanoate, as well.[8][9][10]

Pharmacology

Pharmacodynamics

OHPH is a progestin, or a

subcutaneous injection in animals.[15][16][17] Its potency in animals likewise appears to be similar to that of hydroxyprogesterone caproate.[15][16][17]

Pharmacokinetics

OHPH shows a pronounced

subcutaneous injection in animals, similarly to the closely related medication hydroxyprogesterone caproate.[15][16] The oral activity of OHPH in animals does not appear to have been assessed.[15]

Chemistry

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

OHPH, also known as hydroxyprogesterone enanthate (OHPE),

carbon in its fatty acid ester chain.[1][2]

History

OHPH was first described, along with hydroxyprogesterone caproate and hydroxyprogesterone acetate, by Karl Junkmann of Schering AG in 1954.[16][19] It was introduced for medical use by 1957.[6] OHPH was commercialized by Roussel and Théramex, and has been used clinically in France and Monaco but is no longer marketed.[2][3][4]

Society and culture

Brand names

OHPH has been marketed alone under a number of brand names including H.O.P, Hydroxyprogesterone, Lutogil A.P., and Lutogyl A.P.[1][2][3][4]

Availability

OHPH was previously marketed in France and Monaco but is no longer available.[2][3][22]

See also

References

  1. ^
    ISBN 978-1-4757-2085-3
    .
  2. ^
    ISBN 978-3-88763-075-1
    .
  3. ^
    ISBN 978-3-7692-2114-5
    .
  4. ^
    ISBN 978-3-13-558404-1
    .
  5. ^ a b c Sasco AJ, Gendre I, Verbier-Naneix C, Soulier JL, Raffi F, Satgé D, Robert E (1998). "Neonatal neuroblastoma and in utero exposure to progestagens". International Journal of Risk and Safety in Medicine. 11 (2): 121–128.
  6. ^ a b c d e 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.
  7. ^
    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.
  8. ^ a b c Excerpta medica. Section 8, Neurology and neurosurgery. 1981. p. 10.
  9. ^
    ISBN 978-1-4816-9288-5
    .
  10. ^
    ISBN 9780444420169
    .
  11. ^
    ISBN 978-0-8493-4307-0
    . Progestogens. [...] Hydroxyprogesterone heptanoate. Hydroxyprogesterone (Theramex). Oily solution for injection.
  12. ^
    S2CID 32126275
    .
  13. ^
    PMID 26327902
    .
  14. ^
    PMID 10928425
    .
  15. ^
    ISBN 978-3-662-00826-3
    .
  16. ^
    S2CID 33591186
    .
  17. ^ a b c Junkmann K (1959). Über Entwicklungen auf dem Gestagengebiet. 15. General Assembly of the Japan Medical Congress, Tokyo. Vol. 1. pp. 697–706.
  18. ^ "Formulation".
  19. ^
    ISSN 0022-3263
    .
  20. ISBN 978-1-4832-7276-4
    .
  21. PMID 13828402
    .
  22. ^ "OHPH". micromedexsolutions.com.
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