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Hydroxyprogesterone heptanoate

January 26, 2023

Not to be confused with 17α-Hydroxyprogesterone, Hydroxyprogesterone acetate, or Hydroxyprogesterone caproate.

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 progestin medication used for progestogenic indications.[1][2][3][4] It has been formulated both alone and in together with estrogens, androgens/anabolic steroids, and other progestogens in several combination preparations (brand names Tocogestan, Trioestrine Retard, and Triormon Depositum).[4][5][6][7][8][9][10] OHPH is given by injection into muscle at regular intervals.[11][9]

Hydroxyprogesterone heptanoate
Clinical data
Trade namesH.O.P, Hydroxyprogesterone, 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 classProgestogen; 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
CAS Number
  • 4596-16-1
    1079269-78-5
PubChem CID
  • 94296
ChemSpider
  • 85099
UNII
  • HGN17RX8K8
CompTox Dashboard (EPA)
  • DTXSID70196666
ECHA InfoCard100.022.724
Chemical and physical data
FormulaC28H42O4
Molar mass442.640 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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

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 oil solution for use by intramuscular injection.[3][11] In addition to single-drug preparations, OHPH has also been used in a number of multi-drug formulations.[4][5][6][7][8][9][10] It was used in Tocogestan, a combination of 50 mg progesterone, 200 mg OHPH, and 250 mg α-tocopherol palmitate (vitamin E) in oil solution for use by intramuscular injection.[18][4][5] It was also used in Triormon Depositum (estradiol dibutyrate, testosterone caproate, and OHPH) and Trioestrine Retard (estradiol diundecylate, testosterone cyclohexylpropionate, and OHPH).[6][7] OHPH was a component of the experimental preparation 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 synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[15][12][13][14] The progestogenic potency of OHPH in the uterus is equal to or greater than that of progesterone when administered by 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 depot effect when administered by 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),[19] 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 the more well-known medications hydroxyprogesterone acetate and hydroxyprogesterone caproate (hydroxyprogesterone hexanoate).[1][2] The C3 benzilic acid hydrazone of OHPH, hydroxyprogesterone heptanoate benzilic acid hydrazone (OHPHBH), is known and has been studied in animals.[20][21] In terms of chemical structure, OHPH is very similar to hydroxyprogesterone caproate, differing from it only in having one additional 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. ^ a b c d e f 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 e f g h i Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 532–. ISBN 978-3-88763-075-1.
  3. ^ a b c d e f 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 c d e f g Axel Kleemann; Jürgen Engel (2001). Pharmaceutical Substances: Syntheses, Patents, Applications. Thieme. p. 1033. 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. ^ a b c 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.
  8. ^ a b c Excerpta medica. Section 8, Neurology and neurosurgery. 1981. p. 10.
  9. ^ a b c d Testosterone Congeners—Advances in Research and Application: 2013 Edition: ScholarlyBrief. ScholarlyEditions. 21 June 2013. pp. 137–. ISBN 978-1-4816-9288-5.
  10. ^ a b c 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. ISBN 9780444420169.
  11. ^ a b Leszek Krówczyński (1987). Extended Release Dosage Forms. CRC Press. p. 12. ISBN 978-0-8493-4307-0. Progestogens. [...] Hydroxyprogesterone heptanoate. Hydroxyprogesterone (Theramex). Oily solution for injection.
  12. ^ a b c Schindler, Adolf E. (2014). "The "newer" progestogens and postmenopausal hormone therapy (HRT)". The Journal of Steroid Biochemistry and Molecular Biology. 142: 48–51. doi:10.1016/j.jsbmb.2013.12.003. ISSN 0960-0760. PMID 24333799. S2CID 32126275.
  13. ^ a b c Bińkowska, Małgorzata; Woroń, Jarosław (2015). "Progestogens in menopausal hormone therapy". Menopausal Review. 2 (2): 134–143. doi:10.5114/pm.2015.52154. ISSN 1643-8876. PMC 4498031. PMID 26327902.
  14. ^ a b c Posaci, C.; Smitz, J.; Camus, M.; Osmanagaoglu, K.; Devroey, P. (2000). "Progesterone for the luteal support of assisted reproductive technologies: clinical options". Human Reproduction. 15 (suppl 1): 129–148. doi:10.1093/humrep/15.suppl_1.129. ISSN 0268-1161. PMID 10928425.
  15. ^ a b c d e f Neumann, F; Elger, W; Salloch, RR; Tube, O; Neumann, HF (1969). "Besonderheiten der Wirkungen der einzelnen Gestagene auf Morphologie und Funktion des Genitaltraktes bei Säugetieren" [Special features of the effects of the individual gestagens on the morphology and function of the genital tract in mammals]. Die Gestagene [Progestogens]. Vol. 2. Springer-Verlag. pp. 50–131. ISBN 978-3-662-00826-3.
  16. ^ a b c d e f Junkmann K (1954). "Über protrahiert wirksame Gestagene". Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie. 223 (3). doi:10.1007/BF00246995. S2CID 33591186.
  17. ^ a b c Junkmann, K. (1959). Über Entwicklungen auf dem Gestagengebiet. 15. In Meeting Gen. Assembly of the Japan Medical Congr., Tokyo (Vol. 1, pp. 697-706).
  18. ^ "Formulation".
  19. ^ a b 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.
  20. ^ Ralph I. Dorfman (3 February 2016). Bioassay. Elsevier. pp. 252–. ISBN 978-1-4832-7276-4.
  21. ^ Gleason CH, Parker JM (1959). "The duration of activity of the benziloyl hydrazones of testosterone-17-heptanoate, estrone-3-heptanoate and 17α-hydroxy-progesterone-17-heptanoate". Endocrinology. 65 (3): 508–511. doi:10.1210/endo-65-3-508. ISSN 0013-7227. PMID 13828402.
  22. ^ https://www.micromedexsolutions.com/

January 26, 2023
hydroxyprogesterone, heptanoate, confused, with, 17α, hydroxyprogesterone, hydroxyprogesterone, acetate, hydroxyprogesterone, caproate, this, article, uses, bare, urls, which, uninformative, vulnerable, link, please, consider, converting, them, full, citations. Not to be confused with 17a Hydroxyprogesterone Hydroxyprogesterone acetate or Hydroxyprogesterone caproate This article uses bare URLs which are uninformative and vulnerable to link rot Please consider converting them to full citations to ensure the article remains verifiable and maintains a consistent citation style Several templates and tools are available to assist in formatting such as Reflinks documentation reFill documentation and Citation bot documentation September 2022 Learn how and when to remove this template message 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 progestin medication used for progestogenic indications 1 2 3 4 It has been formulated both alone and in together with estrogens androgens anabolic steroids and other progestogens in several combination preparations brand names Tocogestan Trioestrine Retard and Triormon Depositum 4 5 6 7 8 9 10 OHPH is given by injection into muscle at regular intervals 11 9 Hydroxyprogesterone heptanoateClinical dataTrade namesH O P Hydroxyprogesterone Lutogil A P Lutogyl A P othersOther namesOHPH Hydroxyprogesterone enanthate OHPE 17a Hydroxyprogesterone heptanoate 17a Hydroxyprogesterone heptylate 17a Hydroxypregn 4 ene 3 20 dione 17a heptanoate 17a Heptyloylpregn 4 ene 3 20 dioneRoutes ofadministrationIntramuscular injectionDrug classProgestogen Progestin Progestogen esterATC codeG03DA03 WHO IdentifiersIUPAC name 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 heptanoateCAS Number4596 16 1 1079269 78 5PubChem CID94296ChemSpider85099UNIIHGN17RX8K8CompTox Dashboard EPA DTXSID70196666ECHA InfoCard100 022 724Chemical and physical dataFormulaC 28H 42O 4Molar mass442 640 g mol 13D model JSmol Interactive imageSMILES CCCCCCC O OC1 CCC2C1 CCC3C2CCC4 CC O CCC34C C C O CInChI 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 s1Key NKJYZYWCGKSMSV BDPSOKNUSA NOHPH 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 Contents 1 Medical uses 1 1 Available forms 2 Pharmacology 2 1 Pharmacodynamics 2 2 Pharmacokinetics 3 Chemistry 4 History 5 Society and culture 5 1 Brand names 5 2 Availability 6 See also 7 ReferencesMedical uses EditOHPH is a progestogen and was used in situations in which progestogens were indicated 12 13 14 Available forms Edit OHPH was provided as a 125 mg 1 mL oil solution for use by intramuscular injection 3 11 In addition to single drug preparations OHPH has also been used in a number of multi drug formulations 4 5 6 7 8 9 10 It was used in Tocogestan a combination of 50 mg progesterone 200 mg OHPH and 250 mg a tocopherol palmitate vitamin E in oil solution for use by intramuscular injection 18 4 5 It was also used in Triormon Depositum estradiol dibutyrate testosterone caproate and OHPH and Trioestrine Retard estradiol diundecylate testosterone cyclohexylpropionate and OHPH 6 7 OHPH was a component of the experimental preparation Trophobolene or Trophoboline which also contained estrapronicate estradiol nicotinate propionate and nandrolone undecanoate as well 8 9 10 Pharmacology EditPharmacodynamics Edit OHPH is a progestin or a synthetic progestogen and hence is an agonist of the progesterone receptor the biological target of progestogens like progesterone 15 12 13 14 The progestogenic potency of OHPH in the uterus is equal to or greater than that of progesterone when administered by 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 Edit OHPH shows a pronounced depot effect when administered by 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 EditSee also List of progestogens Progestogen ester and List of progestogen esters OHPH also known as hydroxyprogesterone enanthate OHPE 19 as well as 17a hydroxyprogesterone heptanoate or 17a hydroxypregn 4 ene 3 20 dione 17a heptanoate is a synthetic pregnane steroid and a derivative of progesterone and 17a hydroxyprogesterone 1 2 It is a progestogen ester specifically it is the C17a heptanoate enanthate ester of 17a hydroxyprogesterone 1 2 Analogues of OHPH include the more well known medications hydroxyprogesterone acetate and hydroxyprogesterone caproate hydroxyprogesterone hexanoate 1 2 The C3 benzilic acid hydrazone of OHPH hydroxyprogesterone heptanoate benzilic acid hydrazone OHPHBH is known and has been studied in animals 20 21 In terms of chemical structure OHPH is very similar to hydroxyprogesterone caproate differing from it only in having one additional carbon in its fatty acid ester chain 1 2 History EditOHPH 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 Theramex and has been used clinically in France and Monaco but is no longer marketed 2 3 4 Society and culture EditBrand names Edit 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 Edit OHPH was previously marketed in France and Monaco but is no longer available 2 3 22 See also EditEstradiol dibutyrate hydroxyprogesterone heptanoate testosterone caproate Estradiol diundecylate hydroxyprogesterone heptanoate testosterone cyclohexylpropionate Estrapronicate hydroxyprogesterone heptanoate nandrolone undecanoate Progesterone hydroxyprogesterone heptanoate a tocopherol palmitateReferences Edit a b c d e f 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 a b c d e f g h i Index Nominum 2000 International Drug Directory Taylor amp Francis January 2000 pp 532 ISBN 978 3 88763 075 1 a b c d e f Muller 19 June 1998 European Drug Index European Drug Registrations Fourth Edition CRC Press pp 612 ISBN 978 3 7692 2114 5 a b c d e f g Axel Kleemann Jurgen Engel 2001 Pharmaceutical Substances Syntheses Patents Applications Thieme p 1033 ISBN 978 3 13 558404 1 a b c Sasco AJ Gendre I Verbier Naneix C Soulier JL Raffi F Satge D Robert E 1998 Neonatal neuroblastoma and in utero exposure to progestagens International Journal of Risk and Safety in Medicine 11 2 121 128 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 a b c 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 a b c Excerpta medica Section 8 Neurology and neurosurgery 1981 p 10 a b c d Testosterone Congeners Advances in Research and Application 2013 Edition ScholarlyBrief ScholarlyEditions 21 June 2013 pp 137 ISBN 978 1 4816 9288 5 a b c 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 ISBN 9780444420169 a b Leszek Krowczynski 1987 Extended Release Dosage Forms CRC Press p 12 ISBN 978 0 8493 4307 0 Progestogens Hydroxyprogesterone heptanoate Hydroxyprogesterone Theramex Oily solution for injection a b c Schindler Adolf E 2014 The newer progestogens and postmenopausal hormone therapy HRT The Journal of Steroid Biochemistry and Molecular Biology 142 48 51 doi 10 1016 j jsbmb 2013 12 003 ISSN 0960 0760 PMID 24333799 S2CID 32126275 a b c Binkowska Malgorzata Woron Jaroslaw 2015 Progestogens in menopausal hormone therapy Menopausal Review 2 2 134 143 doi 10 5114 pm 2015 52154 ISSN 1643 8876 PMC 4498031 PMID 26327902 a b c Posaci C Smitz J Camus M Osmanagaoglu K Devroey P 2000 Progesterone for the luteal support of assisted reproductive technologies clinical options Human Reproduction 15 suppl 1 129 148 doi 10 1093 humrep 15 suppl 1 129 ISSN 0268 1161 PMID 10928425 a b c d e f Neumann F Elger W Salloch RR Tube O Neumann HF 1969 Besonderheiten der Wirkungen der einzelnen Gestagene auf Morphologie und Funktion des Genitaltraktes bei Saugetieren Special features of the effects of the individual gestagens on the morphology and function of the genital tract in mammals Die Gestagene Progestogens Vol 2 Springer Verlag pp 50 131 ISBN 978 3 662 00826 3 a b c d e f Junkmann K 1954 Uber protrahiert wirksame Gestagene Naunyn Schmiedebergs Archiv fur Experimentelle Pathologie und Pharmakologie 223 3 doi 10 1007 BF00246995 S2CID 33591186 a b c Junkmann K 1959 Uber Entwicklungen auf dem Gestagengebiet 15 In Meeting Gen Assembly of the Japan Medical Congr Tokyo Vol 1 pp 697 706 Formulation a b Batres E Gomez R Rosenkranz G Sondheimer F 1956 Notes Steroids LXXVI Synthesis of Long Chain Carboxylic Acid Esters of 17a Hydroxyprogesterone The Journal of Organic Chemistry 21 2 240 241 doi 10 1021 jo01108a601 ISSN 0022 3263 Ralph I Dorfman 3 February 2016 Bioassay Elsevier pp 252 ISBN 978 1 4832 7276 4 Gleason CH Parker JM 1959 The duration of activity of the benziloyl hydrazones of testosterone 17 heptanoate estrone 3 heptanoate and 17a hydroxy progesterone 17 heptanoate Endocrinology 65 3 508 511 doi 10 1210 endo 65 3 508 ISSN 0013 7227 PMID 13828402 https www micromedexsolutions com Retrieved from https en wikipedia org w index php title Hydroxyprogesterone heptanoate amp oldid 1112437279, wikipedia, wiki, 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