| 词条 | Dimethyltrienolone | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (7R,8S,13S,14S,17S)-17-hydroxy-7,13,17-trimethyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one | image = 7a17a-dimethyltrenbolone.png | width = 225px | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth | class = Androgen; Anabolic steroid; Progestogen | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 10110-86-8 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 101678228 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 23208745 | UNII = | KEGG = | ChEBI = | ChEMBL = 128880 | synonyms = RU-2420; 7α,17α-Dimethyltrenbolone; 7α,17α-Dimethyl-δ9,11-19-nortestosterone; 7α,17α-Dimethylestra-4,9,11-trien-17β-ol-3-one | C=20 | H=26 | O=2 | molecular_weight = 298.426 g/mol | SMILES = C[C@@H]1CC2=CC(=O)CCC2=C3[C@@H]1[C@@H]4CC[C@]([C@]4(C=C3)C)(C)O | StdInChI_Ref = | StdInChI = 1S/C20H26O2/c1-12-10-13-11-14(21)4-5-15(13)16-6-8-19(2)17(18(12)16)7-9-20(19,3)22/h6,8,11-12,17-18,22H,4-5,7,9-10H2,1-3H3/t12-,17+,18-,19+,20+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = MEMDJKLEPFFNQS-ZGPIAVDESA-N }}Dimethyltrienolone (developmental code name RU-2420) is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use.[1] It has among the highest known affinity of any AAS for the androgen (and progesterone) receptors,[2][3] and has been said to be perhaps the most potent AAS to have ever been developed.[1] PharmacologyPharmacodynamicsDimethyltrienolone is an extremely potent agonist of the androgen and progesterone receptors and hence AAS and progestogen.[1] In animal bioassays, it was shown to possess more than 100 times the anabolic and androgenic potency of the reference AAS methyltestosterone.[1] The drug is not a substrate for 5α-reductase and so is not potentiated or inactivated in so-called "androgenic" tissues like the prostate gland or skin.[1] It is also not a substrate for aromatase and so has no estrogenic activity.[1] Due to its lack of estrogenicity, dimethyltrienolone has no propensity for causing estrogenic side effects like gynecomastia.[1] Because of its C17α methyl group and very high resistance to hepatic metabolism, dimethyltrienolone is said to be exceedingly hepatotoxic.[1]
Chemistry{{See also|List of androgens/anabolic steroids}}Dimethyltrienolone, also known as 7α,17α-dimethyl-δ9,11-19-nortestosterone or as 7α,17α-dimethylestra-4,9,11-trien-17β-ol-3-one, as well as 7α,17α-dimethyltrenbolone, is a synthetic estrane steroid and a 17α-alkylated derivative of nandrolone (19-nortestosterone).[1] It is the 7α,17α-dimethyl derivative of trenbolone and the 7α-methyl derivative of metribolone,[6] as well as the δ9,11 analogue of metribolone and the δ9,11, 17α-methylated derivative of trestolone.[1] HistoryDimethyltrienolone was first described in 1967.[1][7] It was never marketed for medical use.[1] See also
References1. ^1 2 3 4 5 6 7 8 9 10 11 {{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC|year=2009|publisher=Molecular Nutrition Llc|isbn=978-0967930473|pages=212–214}} {{Androgen receptor modulators}}{{Progesterone receptor modulators}}2. ^{{cite journal | vauthors = Waszkowycz B, Clark DE, Frenkel D, Li J, Murray CW, Robson B, Westhead DR | title = PRO_LIGAND: an approach to de novo molecular design. 2. Design of novel molecules from molecular field analysis (MFA) models and pharmacophores | journal = J. Med. Chem. | volume = 37 | issue = 23 | pages = 3994–4002 | year = 1994 | pmid = 7966160 | doi = 10.1021/jm00049a019| url = }} 3. ^{{cite journal | vauthors = Loughney DA, Schwender CF | title = A comparison of progestin and androgen receptor binding using the CoMFA technique | journal = J. Comput.-Aided Mol. Des. | volume = 6 | issue = 6 | pages = 569–81 | year = 1992 | pmid = 1291626 | doi = 10.1007/bf00126215| url = }} 4. ^{{cite journal | vauthors = Delettré J, Mornon JP, Lepicard G, Ojasoo T, Raynaud JP | title = Steroid flexibility and receptor specificity | journal = J. Steroid Biochem. | volume = 13 | issue = 1 | pages = 45–59 | date = January 1980 | pmid = 7382482 | doi = 10.1016/0022-4731(80)90112-0 | url = }} 5. ^{{cite journal | vauthors = Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP | title = Towards the mapping of the progesterone and androgen receptors | journal = J. Steroid Biochem. | volume = 27 | issue = 1-3 | pages = 255–69 | date = 1987 | pmid = 3695484 | doi = 10.1016/0022-4731(87)90317-7 | url = }} 6. ^{{cite book|author1=D. Ganten|author2=D. Pfaff|title=Actions of Progesterone on the Brain|url=https://books.google.com/books?id=CFEICQAAQBAJ&pg=PA17|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-69728-9|pages=17–}} 7. ^{{cite book | last = Mathieu | first = J | title = Proceedings of the International Symposium on Drug Research, Montreal, Canada, June 12-14, 1967 | year = 1967 | page = 134 | publisher = Chemical Institute of Canada, Medical Chemistry Group, Montreal, Canada | url = https://books.google.com/books/about/Proceedings_of_the_International_Symposi.html?id=A69ZnQAACAAJ}} 6 : Alcohols|Androgens and anabolic steroids|Estranes|Hepatotoxins|Ketones|Progestogens |
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