Chemical compound
Pharmaceutical compound
Hydroxyprogesterone heptanoate Clinical data Trade names H.O.P, Hydroxyprogesterone, Lutogil A.P., Lutogyl A.P., others Other names 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 Intramuscular injection Drug class Progestogen ;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 PubChem CID ChemSpider UNII CompTox Dashboard (EPA) ECHA InfoCard 100.022.724 Chemical and physical data Formula C 28 H 42 O 4 Molar mass −1 3D model (JSmol ) 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 ashydroxyprogesterone enanthate (OHPE ) and sold under the brand namesH.O.P. ,Lutogil A.P. , andLutogyl A.P. among others, is aprogestin medication used forprogestogenic indications.[ 1] [ 2] [ 3] [ 4] estrogens ,androgens /anabolic steroids , and otherprogestogens in severalcombination preparations (brand namesTocogestan ,Trioestrine Retard , andTriormon Depositum ).[ 4] [ 5] [ 6] [ 7] [ 8] [ 9] [ 10] injection into muscle at regular intervals.[ 11] [ 9]
OHPH is a progestin, or asynthetic progestogen , and hence is anagonist of theprogesterone receptor , thebiological target of progestogens likeprogesterone .[ 12] [ 13] [ 14] pharmacology to that of the closely related medicationhydroxyprogesterone caproate (OHPC).[ 15] [ 16] [ 17]
OHPH was first described by 1954[ 16] [ 6] France andMonaco in the past but is no longer marketed.[ 2] [ 3] [ 4]
OHPH is aprogestogen and was used in situations in which progestogens were indicated.[ 12] [ 13] [ 14]
OHPH was provided as a 125 mg/1 mLoil solution for use byintramuscular injection .[ 3] [ 11] [ 4] [ 5] [ 6] [ 7] [ 8] [ 9] [ 10] Tocogestan , a combination of 50 mgprogesterone , 200 mg OHPH, and 250 mgα-tocopherol palmitate (vitamin E ) inoil solution for use by intramuscular injection.[ 18] [ 4] [ 5] Triormon Depositum (estradiol dibutyrate ,testosterone caproate , and OHPH) andTrioestrine Retard (estradiol diundecylate ,testosterone cyclohexylpropionate , and OHPH).[ 6] [ 7] Trophobolene (or Trophoboline), which also containedestrapronicate (estradiol nicotinate propionate) andnandrolone undecanoate , as well.[ 8] [ 9] [ 10]
OHPH is a progestin, or asynthetic progestogen , and hence is anagonist of theprogesterone receptor , thebiological target of progestogens likeprogesterone .[ 15] [ 12] [ 13] [ 14] uterus is equal to or greater than that ofprogesterone when administered bysubcutaneous injection in animals.[ 15] [ 16] [ 17] hydroxyprogesterone caproate .[ 15] [ 16] [ 17]
OHPH shows a pronounceddepot effect when administered bysubcutaneous injection in animals, similarly to the closely related medicationhydroxyprogesterone caproate .[ 15] [ 16] oral activity of OHPH in animals does not appear to have been assessed.[ 15]
OHPH, also known as hydroxyprogesterone enanthate (OHPE),[ 19] synthetic pregnane steroid and aderivative ofprogesterone and17α-hydroxyprogesterone .[ 1] [ 2] progestogen ester ; specifically, it is the C17αheptanoate (enanthate)ester of 17α-hydroxyprogesterone.[ 1] [ 2] Analogues of OHPH include the more well-known medicationshydroxyprogesterone acetate andhydroxyprogesterone caproate (hydroxyprogesterone hexanoate).[ 1] [ 2] benzilic acid hydrazone of OHPH,hydroxyprogesterone heptanoate benzilic acid hydrazone (OHPHBH), is known and has been studied in animals.[ 20] [ 21] chemical structure , OHPH is very similar to hydroxyprogesterone caproate, differing from it only in having one additionalcarbon in itsfatty acid ester chain .[ 1] [ 2]
OHPH was first described, along withhydroxyprogesterone caproate andhydroxyprogesterone acetate , by Karl Junkmann ofSchering AG in 1954.[ 16] [ 19] [ 6] Roussel andThéramex , and has been used clinically inFrance andMonaco but is no longer marketed.[ 2] [ 3] [ 4]
Society and culture [ 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]
OHPH was previously marketed inFrance andMonaco but is no longer available.[ 2] [ 3] [ 22]
^a b c d e f Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 ^a b c d e f g h i Index Nominum 2000: International Drug Directory ISBN 978-3-88763-075-1 ^a b c d e f Muller NF, Dessing RP (19 June 1998).European Drug Index: European Drug Registrations ISBN 978-3-7692-2114-5 ^a b c d e f g Kleemann A, Engel J (2001).Pharmaceutical Substances: Syntheses, Patents, Applications ISBN 978-3-13-558404-1 ^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. ^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 P (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 ^a b c d "Nandarolone" .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 Frigerio A (1981).Chromatography in Biochemistry, Medicine and Environmental Research: Proceedings of the ... International Symposium on Chromatography in Biochemistry, Medicine and Environmental Research ISBN 9780444420169 ^a b Krówczyński L (1987).Extended Release Dosage Forms ISBN 978-0-8493-4307-0 Progestogens. [...] Hydroxyprogesterone heptanoate. Hydroxyprogesterone (Theramex). Oily solution for injection. ^a b c Schindler AE (July 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 .PMID 24333799 .S2CID 32126275 . ^a b c Bińkowska M, Woroń J (June 2015)."Progestogens in menopausal hormone therapy" .Przeglad Menopauzalny = Menopause Review .14 (2):134– 143.doi :10.5114/pm.2015.52154 .PMC 4498031 PMID 26327902 . ^a b c Posaci C, Smitz J, Camus M, Osmanagaoglu K, Devroey P (June 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 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 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 ^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 . ^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. ^ "Formulation" .^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 . ^ Shipley EG (1962)."Anti-gonadotropic steroids, inhibition of ovulation and mating" . In Dorfman RI (ed.).Methods in Hormone Research . Vol. 2. Elsevier. pp. 252–.ISBN 978-1-4832-7276-4 {{cite book }}:ISBN / Date incompatibility (help ) ^ 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 . ^ "OHPH" .micromedexsolutions.com .
PR Tooltip Progesterone receptor
Agonists Testosterone derivatives: Progestins:6,6-Difluoronorethisterone 6,6-Difluoronorethisterone acetate 17α-Allyl-19-nortestosterone Allylestrenol Altrenogest Chloroethynylnorgestrel Cingestol Danazol Desogestrel Dienogest Ethinylandrostenediol Ethisterone Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel esters (e.g.,levonorgestrel butanoate )Lynestrenol Lynestrenol phenylpropionate Metynodiol Metynodiol diacetate Norelgestromin Norethisterone (norethindrone) Norethisterone esters (e.g.,norethisterone acetate ,norethisterone enanthate )Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tibolone Tigestol Tosagestin ; Anabolic–androgenic steroids:11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione 19-Nordehydroepiandrosterone Bolandiol Bolandiol dipropionate Bolandione Dimethisterone Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethyldienolone Dimethyltrienolone Ethyldienolone Ethylestrenol (ethylnandrol) Methyldienolone Metribolone (R-1881) Methoxydienone (methoxygonadiene) Mibolerone Nandrolone Nandrolone esters (e.g.,nandrolone decanoate ,nandrolone phenylpropionate )Norethandrolone Normethandrone (methylestrenolone, normethandrolone, normethisterone) RU-2309 Tetrahydrogestrinone Trenbolone (trienolone) Trenbolone esters (e.g.,trenbolone acetate ,trenbolone enanthate )Trendione Trestolone Trestolone acetate MixedSPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor PAQR Tooltip Progestin and adipoQ receptor )
