| 词条 | Cyanoketone |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424937956 | IUPAC_name = (2S,8R,9S,10R,13S,14S,17S)-17-hydroxy-4,4,10,13,17-pentamethyl-3-oxo-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-2-carbonitrile | image = Cyanoketone.png | width = 225px | 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 = 4248-66-2 | CAS_supplemental = | class = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 20243 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 19069 | UNII = | KEGG = | ChEBI = | ChEMBL = | synonyms = Cyanotrimethylandrostenolone; CTM; 2α-Cyano-4,4',17α-trimethylandrost-5-en-17β-ol-3-one | C=23 | H=33 | N=1 | O=2 | molecular_weight = 355.51 g/mol | SMILES = N#C[C@H]4C(=O)C(C\\3=C\\C[C@@H]2[C@H](CC[C@]1([C@H]2CC[C@@]1(O)C)C)[C@@]/3(C)C4)(C)C | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C23H33NO2/c1-20(2)18-7-6-15-16(21(18,3)12-14(13-24)19(20)25)8-10-22(4)17(15)9-11-23(22,5)26/h7,14-17,26H,6,8-12H2,1-5H3/t14-,15+,16-,17-,21+,22-,23-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = GTBRTGPZZALPNS-MXHVRSFHSA-N }}Cyanoketone, also known as 2α-cyano-4,4',17α-trimethylandrost-5-en-17β-ol-3-one (CTM),[1] is a synthetic androstane steroid and a steroidogenesis inhibitor which is used in scientific research.[2][3][4] On account of its structural similarity to pregnenolone, cyanoketone binds to and acts as a potent, selective, and irreversible inhibitor of 3β-hydroxysteroid dehydrogenase (3β-HSD),[1][5] an enzyme that is responsible for the conversion of pregnenolone into progesterone, 17α-hydroxypregnenolone into 17α-hydroxyprogesterone, {{abbrlink|DHEA|dehydroepiandrosterone}} into androstenedione, and androstenediol into testosterone.[2][3][6] As such, cyanoketone inhibits the production of both gonadal and adrenal steroids, including progesterone,[5] androgens, estrogens, and corticosteroids.[3][6] The drug is too toxic for therapeutic use in humans, and so has been used instead exclusively as a research tool.[2][3] See also
References1. ^1 {{cite book|author1=I. Chester Jones|author2=I. W. Henderson|title=General, Comparative and Clinical Endocrinology of the Adrenal Cortex|url=https://books.google.com/books?id=iHrAAgAAQBAJ&pg=PA136|date=22 October 2013|publisher=Elsevier Science|isbn=978-1-4832-5980-2|pages=136–}} {{Steroid-stub}}2. ^1 2 {{cite book|author1=John A. Thomas|author2=Edward J. Keenan|title=Principles of Endocrine Pharmacology|url=https://books.google.com/books?id=mTagBQAAQBAJ&pg=PA280|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4684-5036-1|pages=280–}} 3. ^1 2 3 {{cite book|author1=John A. Thomas|author2=Edward J. Keenan|title=Principles of Endocrine Pharmacology|url=https://books.google.com/books?id=mTagBQAAQBAJ&pg=PA11|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4684-5036-1|pages=11–12}} 4. ^{{Cite journal | doi = 10.1159/000301873 | last1 = Di Prisco | first1 = C. L. | last2 = Materazzi | first2 = G. | last3 = Scattolini | first3 = B. | title = Inhibition of steroidogenesis by cyanoketone | journal = Gynecologic and Obstetric Investigation | volume = 2 | issue = 1 | pages = 309–315 | year = 1971 | pmid = 4266510}} 5. ^1 {{cite book|author=Barry D. Bavister|title=Preimplantation Embryo Development|url=https://books.google.com/books?id=1I-1BwAAQBAJ&pg=PA30|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4613-9317-7|pages=30–}} 6. ^1 {{cite book|author1=David O. Norris|author2=James A. Carr|title=Vertebrate Endocrinology|url=https://books.google.com/books?id=F_NaW1ZcSSAC&pg=PA71|date=4 May 2013|publisher=Academic Press|isbn=978-0-12-396465-6|pages=71–}} 8 : 3β-Hydroxysteroid dehydrogenase inhibitors|Abandoned drugs|Alcohols|Androstanes|Cholesterol side-chain cleavage enzyme inhibitors|CYP17A1 inhibitors|Ketones|Nitriles |
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