| 词条 | Hydroxyprogesterone heptanoate |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_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] heptanoate | image = Hydroxyprogesterone heptanoate.svg | width = 250px | tradename = H.O.P, Lutogil A.P., Lutogyl A.P., others | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = Intramuscular injection | class = Progestin; Progestogen; Progestogen ester | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 4596-16-1 | CAS_supplemental = 1079269-78-5 | ATC_prefix = G03 | ATC_suffix = DA03 | PubChem = 94296 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 85099 | UNII_Ref = | UNII = HGN17RX8K8 | 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 | C=28 | H=42 | O=4 | molecular_weight = 442.631 g/mol | SMILES = CCCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(=O)C | StdInChI = 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 | StdInChIKey = NKJYZYWCGKSMSV-BDPSOKNUSA-N }}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{{See also|List of progestogens|Progestogen ester|List of progestogen esters}}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] References1. ^1 2 3 {{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA665|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=665–}} {{Progestogens and antiprogestogens}}{{Progesterone receptor modulators}}{{Genito-urinary-drug-stub}}{{Steroid-stub}}2. ^1 2 3 {{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA532|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=532–}} 3. ^{{cite book|author=Muller|title=European Drug Index: European Drug Registrations, Fourth Edition|url=https://books.google.com/books?id=2HBPHmclMWIC&pg=PA612|date=19 June 1998|publisher=CRC Press|isbn=978-3-7692-2114-5|pages=612–}} 4. ^1 {{cite book|author1=Axel Kleemann|author2=Jürgen Engel|title=Pharmaceutical Substances: Syntheses, Patents, Applications|url=https://books.google.com/books?id=ym5qAAAAMAAJ|year=2001|publisher=Thieme|isbn=978-3-13-558404-1|page=1033}} 5. ^{{cite book|title=Excerpta medica. Section 8, Neurology and neurosurgery|url=https://books.google.com/books?id=_qiaAAAAIAAJ|year=1981|page=10}} 6. ^{{cite book|title=Testosterone Congeners—Advances in Research and Application: 2013 Edition: ScholarlyBrief|url=https://books.google.com/books?id=CR-NH3HzlSkC&pg=PA137|date=21 June 2013|publisher=ScholarlyEditions|isbn=978-1-4816-9288-5|pages=137–}} 7. ^{{cite book|author=Alberto Frigerio|title=Chromatography in Biochemistry, Medicine and Environmental Research: Proceedings of the ... International Symposium on Chromatography in Biochemistry, Medicine and Environmental Research|url=https://books.google.com/books?id=bbTwAAAAMAAJ|year=1981|publisher=Elsevier Scientific Publishing Company|page=99}} 8. ^https://www.google.com/patents/US6774122 9. ^http://content.iospress.com/articles/international-journal-of-risk-and-safety-in-medicine/jrs132 10. ^{{cite journal | last1 = Ermiglia | first1 = G | last2 = Valli | first2 = P | title = Triormon depositum in climacteric syndrome. Curves of excretion of catabolites and duration of the therapeutic effect | journal = Quaderni clin. ostet. e ginecol. | volume = 12 | pages = 284-93 | year = 1957 | quote = 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. ^{{cite journal | last = Bordier | first = Philippe | title = Cure of fifteen osteoporosis cases by a delayed effect of hormonal association | journal = Semaine des Hopitaux | volume = 39 | issue = 2 | pages = 81-4 | year = 1963 | issn = 0037-1777 | quote = 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. ^{{cite journal|last1=Batres|first1=E.|last2=Gomez|first2=R.|last3=Rosenkranz|first3=G.|last4=Sondheimer|first4=F.|title=Notes - Steroids. LXXVI. Synthesis of Long Chain Carboxylic Acid Esters of 17α-Hydroxyprogesterone|journal=The Journal of Organic Chemistry|volume=21|issue=2|year=1956|pages=240–241|issn=0022-3263|doi=10.1021/jo01108a601}} 7 : Abandoned drugs|Alcohols|Diketones|Esters|Pregnanes|Progestogen esters|Progestogens |
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