| 词条 | 17β-Dihydroequilin |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (9S,13S,14S,17S)-13-Methyl-6,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthrene-3,17-diol | image = 17β-Dihydroequilin.svg | 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 = Estrogen | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 3563-27-7 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 11954027 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 10128322 | UNII = WXG88DST4R | KEGG = | ChEBI = 62851 | ChEMBL = 121458 | synonyms = β-Dihydroequilin; Δ7-17β-Estradiol; 7-Dehydro-17β-estradiol; Estra-1,3,5(10),7-tetraen-3,17β-diol; NSC-12170 | C=18 | H=22 | O=22 | molecular_weight = 270.366 g/mol | SMILES = C[C@]12CC[C@H]3C(=CCC4=C3C=CC(=C4)O)[C@@H]1CC[C@@H]2O | StdInChI_Ref = | StdInChI = 1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3-5,10,14,16-17,19-20H,2,6-9H2,1H3/t14-,16+,17+,18+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = NLLMJANWPUQQTA-UBDQQSCGSA-N }}17β-Dihydroequilin is a naturally occurring estrogen sex hormone found in horses as well as a medication.[1][2] As the C3 sulfate ester sodium salt, it is a minor constituent (1.7%) of conjugated estrogens (CEEs; brand name Premarin).[1] However, as equilin, with equilin sulfate being a major component of CEEs, is transformed into 17β-dihydroequilin in the body, analogously to the conversion of estrone into estradiol, 17β-dihydroequilin is, along with estradiol, the most important estrogen responsible for the effects of CEEs.[1] PharmacologyPharmacodynamics17β-Dihydroequilin is an estrogen, or an agonist of the estrogen receptors (ERs), the ERα and ERβ.[1] In terms of relative binding affinity for the ERs, 17β-dihydroequilin has about 113% and 108% of that of estradiol for the ERα and ERβ, respectively.[1] 17β-Dihydroequilin has about 83% of the relative potency of CEEs in the vagina and 200% of the relative potency of CEEs in the uterus.[1] Of the equine estrogens, it shows the highest estrogenic activity and greatest estrogenic potency.[1] Like CEEs as a whole, 17β-dihydroequilin has disproportionate effects in certain tissues such as the liver and uterus.[1] Equilin, the second major component of conjugated estrogens after estrone, is reversibly transformed into 17β-dihydroequilin analogously to the transformation of estrone into estradiol.[1] However, whereas the balance of mutual interconversion of estrone and estradiol is largely shifted in the direction of estrone, it is nearly equal in the case of equilin and 17β-dihydroequilin.[1] As such, although 17β-dihydroequilin is only a minor constituent of CEEs, it is, along with estradiol, the most important estrogen relevant to the estrogenic activity of the medication.[1] {{Composition of conjugated estrogens and properties of constituents}}{{Relative oral potencies of estrogens}}Pharmacokinetics17β-Dihydroequilin has about 30% of the relative binding affinity of testosterone for sex hormone-binding globulin (SHBG), relative to 50% for estradiol.[1] The metabolic clearance rate of 17β-dihydroequilin is 1,250 L/day/m2, relative to 580 L/day/m2 for estradiol.[1] Chemistry{{See also|List of estrogens#Equine estrogens}}17β-Dihydroequilin, or simply β-dihydroequilin, also known as δ7-17β-estradiol or as 7-dehydro-17β-estradiol, as well as estra-1,3,5(10),7-tetraen-3,17β-diol, is a naturally occurring estrane steroid and an analogue of estradiol.[1] In terms of chemical structure and pharmacology, equilin (δ7-estrone) is to 17β-dihydroequilin as estrone is to estradiol.[1] References1. ^1 2 3 4 5 6 7 8 9 10 11 12 13 14 {{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 Suppl 1 | issue = | pages = 3–63 | year = 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | url = http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf}} {{Estrogens and antiestrogens}}{{Estrogen receptor modulators}}{{DEFAULTSORT:Dihydroequilin, 17β-}}2. ^{{cite book|author1=Marc A. Fritz|author2=Leon Speroff|title=Clinical Gynecologic Endocrinology and Infertility|url=https://books.google.com/books?id=KZLubBxJEwEC&pg=PA751|date=28 March 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-4847-3|pages=751–}} 4 : Diols|Estranes|Estrogens|Human drug metabolites |
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