| 词条 | Roxibolone |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 444480217 | IUPAC_name = (8S,9S,10R,11S,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-2-carboxylic acid | image = Roxibolone.png | width = 250 | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 60023-92-9 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 68795 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 62035 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 3R7NLP419C | KEGG = | ChEBI = | ChEMBL = | C=21 | H=28 | O=5 | molecular_weight = 360.44 g/mol | SMILES = C[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C(=C[C@]34C)C(=O)O)O)C)O | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C21H28O5/c1-19-9-13(18(24)25)15(22)8-11(19)4-5-12-14-6-7-21(3,26)20(14,2)10-16(23)17(12)19/h8-9,12,14,16-17,23,26H,4-7,10H2,1-3H3,(H,24,25)/t12-,14-,16-,17+,19-,20-,21-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = JOFBZBDWOWPUMO-QARKFJNLSA-N | synonyms = BR-906; 11β,17β-Dihydroxy-17α-methyl-3-oxoandrosta-1,4-diene-2-carboxylic acid }}Roxibolone (INN) (developmental code name BR-906), also known as 11β,17β-dihydroxy-17α-methyl-3-oxoandrosta-1,4-diene-2-carboxylic acid, is a steroidal antiglucocorticoid described as an anticholesterolemic (cholesterol-lowering) and anabolic drug which was never marketed.[1][2] Roxibolone is closely related to formebolone, which shows antiglucocorticoid activity similarly and, with the exception of having a carboxaldehyde group at the C2 position instead of a carboxylic acid group, roxibolone is structurally almost identical to.[2] The 2-decyl ester of roxibolone, decylroxibolone (developmental code name BR-917), is a long-acting prodrug of roxibolone with similar activity.[1][2] In rats, roxibolone counteracts the catabolic effects (control of nitrogen balance) and increased alkaline phosphatase levels induced by the potent glucocorticoid dexamethasone phosphate.[2] It does not bind to the glucocorticoid receptor however, and its antiglucocorticoid activity may instead be mediated by enzyme inhibition.[3] In accordance, 11α- and 11β-hydroxyprogesterone are known to be potent inhibitors of 11β-hydroxysteroid dehydrogenase (11β-HSD), which is responsible for the biosynthesis of the potent endogenous glucocorticoids cortisol and corticosterone (from the precursors deoxycortisol and deoxycorticosterone, respectively).[4][5] As roxibolone is 11β-hydroxylated similarly, it may act in a likewise fashion. However, formebolone was found to be a very weak inhibitor of 11β-HSD type 2, although this specific isoenzyme is responsible for the inactivation of glucocorticoids rather than their production.[6] Unlike formebolone, which is additionally an anabolic-androgenic steroid (AAS), roxibolone is devoid of affinity for the androgen receptor and possesses no androgenic or myotrophic activity in animal assays.[2] For this reason, it has been said that roxibolone may be much better tolerated in comparison.[2] References1. ^1 {{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=RA1-PA586|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|page=1082}} {{steroid-stub}}{{systemic-hormonal-drug-stub}}2. ^1 2 3 4 5 {{cite journal |vauthors=Felippone F, Resnati G, Scolastico C, Tronconi G |title=Synthesis of 2-carboxy-11 beta, 17 beta-dihydroxy-17-methyl-1, 4-androstadien-3-one and related compounds |journal=Steroids |volume=43 |issue=3 |pages=271–82 |year=1984 |pmid=6523544 |doi= 10.1016/0039-128x(84)90045-x|url=}} 3. ^{{cite journal |vauthors=Dahlberg E, Snochowski M, Gustafsson JA |title=Regulation of the androgen and glucocorticoid receptors in rat and mouse skeletal muscle cytosol |journal=Endocrinology |volume=108 |issue=4 |pages=1431–40 |year=1981 |pmid=6970661 |doi=10.1210/endo-108-4-1431 |url=}} 4. ^{{cite journal | vauthors = Souness GW, Latif SA, Laurenzo JL, Morris DJ | title = 11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase (isoforms 1 and 2), confer marked mineralocorticoid activity on corticosterone in the ADX rat | journal = Endocrinology | volume = 136 | issue = 4 | pages = 1809–12 | year = 1995 | pmid = 7895695 | doi = 10.1210/endo.136.4.7895695 | url = }} 5. ^{{cite journal | vauthors = Souness GW, Morris DJ | title = 11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase, possess hypertensinogenic activity in the rat | journal = Hypertension | volume = 27 | issue = 3 Pt 1 | pages = 421–5 | year = 1996 | pmid = 8698448 | doi = 10.1161/01.hyp.27.3.421| url = }} 6. ^{{cite journal |vauthors=Fürstenberger C, Vuorinen A, Da Cunha T, Kratschmar DV, Saugy M, Schuster D, Odermatt A |title=The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation |journal=Toxicol. Sci. |volume=126 |issue=2 |pages=353–61 |year=2012 |pmid=22273746 |doi=10.1093/toxsci/kfs022 |url=}} 5 : Androstanes|Antiglucocorticoids|Carboxylic acids|Hypolipidemic agents|Ketones |
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