| 词条 | 7α-Thiomethylspironolactone |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-7-methylsulfanylspiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione | image = 7α-Thiomethylspironolactone.svg | width = 225px | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | class = Antimineralocorticoid | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 38753-77-4 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 162325 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 142539 | UNII = | KEGG = | ChEBI = | ChEMBL = 3544705 | synonyms = 7α-TMS; SC-26519; 17α-Hydroxy-7α-(methylthio)-3-oxopregn-4-ene-21-carboxylic acid γ-lactone | C=23 | H=32 | O=3 | S=1 | SMILES = C[C@]12CCC(=O)C=C1C[C@H]([C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]45CCC(=O)O5)C)SC | StdInChI_Ref = | StdInChI = 1S/C23H32O3S/c1-21-8-4-15(24)12-14(21)13-18(27-3)20-16(21)5-9-22(2)17(20)6-10-23(22)11-7-19(25)26-23/h12,16-18,20H,4-11,13H2,1-3H3/t16-,17-,18+,20+,21-,22-,23+/m0/s1 | StdInChIKey_Ref = | StdInChIKey = FWRDLPQBEOKIRE-RJKHXGPOSA-N }}7α-Thiomethylspironolactone (7α-TMS; developmental code name SC-26519) is a steroidal antimineralocorticoid and antiandrogen of the spirolactone group and the major active metabolite of spironolactone.[1] Other important metabolites of spironolactone include 7α-thiospironolactone (7α-TS; SC-24813), 6β-hydroxy-7α-thiomethylspironolactone (6β-OH-7α-TMS), and canrenone (SC-9376).[2][3][4][5] Spironolactone is a prodrug with a short terminal half-life of 1.4 hours.[6][7][8] The active metabolites of spironolactone have extended terminal half-lives of 13.8 hours for 7α-TMS, 15.0 hours for 6β-OH-7α-TMS, and 16.5 hours for canrenone, and accordingly, these metabolites are responsible for the therapeutic effects of the drug.[6][7] 7α-TS and 7α-TMS have been found to possess approximately equivalent affinity for the rat ventral prostate androgen receptor (AR) relative to that of spironolactone.[9] The affinity of 7α-TS, 7α-TMS, and spironolactone for the rat prostate AR is about 3.0 to 8.5% of that of dihydrotestosterone (DHT).[9] {{Pharmacokinetics of 100 mg per day spironolactone and its metabolites}}7α-TMS has been found to account for around 80% of the potassium-sparing effect of spironolactone,[10][11][12] whereas canrenone accounts for the remaining approximate 10 to 25% of the potassium-sparing effect of the drug.[13] See also
References1. ^{{cite journal | vauthors = Yang J, Young MJ | title = Mineralocorticoid receptor antagonists-pharmacodynamics and pharmacokinetic differences | journal = Curr Opin Pharmacol | volume = 27 | issue = | pages = 78–85 | year = 2016 | pmid = 26939027 | doi = 10.1016/j.coph.2016.02.005 | url = }} 2. ^{{cite journal | vauthors = Parthasarathy HK, MacDonald TM | title = Mineralocorticoid receptor antagonists | journal = Curr. Hypertens. Rep. | volume = 9 | issue = 1 | pages = 45–52 | year = 2007 | pmid = 17362671 | doi = | url = }} 3. ^{{cite journal | vauthors = Kolkhof P, Bärfacker L | title = 30 YEARS OF THE MINERALOCORTICOID RECEPTOR: Mineralocorticoid receptor antagonists: 60 years of research and development | journal = J. Endocrinol. | volume = 234 | issue = 1 | pages = T125–T140 | year = 2017 | pmid = 28634268 | pmc = 5488394 | doi = 10.1530/JOE-16-0600 | url = }} 4. ^{{cite journal | vauthors = Yang J, Young MJ | title = Mineralocorticoid receptor antagonists-pharmacodynamics and pharmacokinetic differences | journal = Curr Opin Pharmacol | volume = 27 | issue = | pages = 78–85 | year = 2016 | pmid = 26939027 | doi = 10.1016/j.coph.2016.02.005 | url = }} 5. ^{{cite journal | vauthors = Doggrell SA, Brown L | title = The spironolactone renaissance | journal = Expert Opin Investig Drugs | volume = 10 | issue = 5 | pages = 943–54 | year = 2001 | pmid = 11322868 | doi = 10.1517/13543784.10.5.943 | url = }} 6. ^1 {{cite journal | vauthors = Sica DA | title = Pharmacokinetics and pharmacodynamics of mineralocorticoid blocking agents and their effects on potassium homeostasis | journal = Heart Fail Rev | volume = 10 | issue = 1 | pages = 23–9 | year = 2005 | pmid = 15947888 | doi = 10.1007/s10741-005-2345-1 | url = }} 7. ^1 {{cite journal | vauthors = Maron BA, Leopold JA | title = Mineralocorticoid receptor antagonists and endothelial function | journal = Curr Opin Investig Drugs | volume = 9 | issue = 9 | pages = 963–9 | year = 2008 | pmid = 18729003 | pmc = 2967484 | doi = | url = }} 8. ^{{cite book|title=Oxford Textbook of Medicine: Vol. 1|url=https://books.google.com/books?id=_s65U1n9Lf8C&pg=RA1-PA962|year=2003|publisher=Oxford University Press|isbn=978-0-19-262922-7|pages=1–}} 9. ^1 {{cite journal | vauthors = Cutler GB, Pita JC, Rifka SM, Menard RH, Sauer MA, Loriaux DL | title = SC 25152: A potent mineralocorticoid antagonist with reduced affinity for the 5 alpha-dihydrotestosterone receptor of human and rat prostate | journal = J. Clin. Endocrinol. Metab. | volume = 47 | issue = 1 | pages = 171–5 | year = 1978 | pmid = 263288 | doi = 10.1210/jcem-47-1-171 | url = }} 10. ^{{cite journal | vauthors = Maron BA, Leopold JA | title = Mineralocorticoid receptor antagonists and endothelial function | journal = Curr Opin Investig Drugs | volume = 9 | issue = 9 | pages = 963–9 | year = 2008 | pmid = 18729003 | pmc = 2967484 | doi = | url = }} 11. ^{{cite book|author1=International Agency for Research on Cancer|author2=World Health Organization|title=Some Thyrotropic Agents|url=https://books.google.com/books?id=l965aqw_LSkC&pg=PA325|year=2001|publisher=World Health Organization|isbn=978-92-832-1279-9|pages=325–}} 12. ^{{cite journal | vauthors = Agusti G, Bourgeois S, Cartiser N, Fessi H, Le Borgne M, Lomberget T | title = A safe and practical method for the preparation of 7α-thioether and thioester derivatives of spironolactone | journal = Steroids | volume = 78 | issue = 1 | pages = 102–7 | year = 2013 | pmid = 23063964 | doi = 10.1016/j.steroids.2012.09.005 | url = }} 13. ^{{cite book|author1=Pere Ginés|author2=Vicente Arroyo|author3=Juan Rodés |author4=Robert W. Schrier |title=Ascites and Renal Dysfunction in Liver Disease: Pathogenesis, Diagnosis, and Treatment|url=https://books.google.com/books?id=Z3PARx4oYDgC&pg=PR6|date=15 April 2008|publisher=John Wiley & Sons|isbn=978-1-4051-4370-7|page=[https://www.researchgate.net/profile/Carlos_Terra/publication/227982015_Hepatorenal_Syndrome_in_Cirrhosis_Clinical_Features_Diagnosis_and_Management/links/54479d460cf2d62c30508b3b.pdf#page=234 229]}} Further reading
8 : Antimineralocorticoids|Human drug metabolites|Lactones|Organosulfur compounds|Pregnanes|Spiro compounds|Spironolactone|Steroidal antiandrogens |
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