| 词条 | 5α-Dihydrolevonorgestrel |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (5S,8R,9R,10S,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-one | image = 5α-Dihydrolevonorgestrel.svg | width = 225px | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | class = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 78088-19-4 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 9995794 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 8171375 | UNII = 7Z4S6960I5 | KEGG = | ChEBI = | ChEMBL = | synonyms = 5α-Dihydrolevonorgestrel; 5α-DHLNG; 5α-LNG | C=21 | H=30 | O=2 | molecular_weight = 314.469 g/mol | SMILES = CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CC[C@@H]4[C@@H]3CCC(=O)C4 | StdInChI_Ref = | StdInChI = 1S/C21H30O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,14,16-19,23H,3,5-13H2,1H3/t14-,16-,17+,18+,19-,20-,21-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = BMVIRDJAPBCAPQ-WQGSDSCCSA-N }}5α-Dihydrolevonorgestrel (5α-DHLNG) is an active metabolite of the progestin levonorgestrel which is formed by 5α-reductase.[1][2] It has about one-third of the affinity of levonorgestrel for the progesterone receptor.[1] In contrast to levonorgestrel, the compound has both progestogenic and antiprogestogenic activity, and hence has a selective progesterone receptor modulator-like profile of activity.[3][4] This is analogous to the case of norethisterone and 5α-dihydronorethisterone.[3][5] In addition to the progesterone receptor, 5α-DHLNG interacts with the androgen receptor.[6] It has similar affinity for the androgen receptor relative to levonorgestrel (34.3% of that of metribolone for levonorgestrel and 38.0% of that of metribolone for 5α-DHLNG), and has androgenic effects similarly to levonorgestrel and testosterone.[6] 5α-DHLNG is further transformed into 3α,5α- and 3β,5α-{{abbr|THLNG|tetrahydrolevonorgestrel}}, which bind weakly to the estrogen receptor (0.4 to 2.4% of the {{abbr|RBA|relative binding affinity}} of {{abbrlink|E2|estradiol (medication)}}) and have weak estrogenic activity.[7][8][4] These metabolites are considered to be responsible for the weak estrogenic activity of high doses of levonorgestrel.[8][4]{{Relative affinities of levonorgestrel and metabolites}} See also
References1. ^1 {{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}} {{Androgen receptor modulators}}{{Estrogen receptor modulators}}{{Progesterone receptor modulators}}{{DEFAULTSORT:Dihydrolevonorgestrel, 5α-}}2. ^{{cite journal | vauthors = Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH | title = Classification and pharmacology of progestins | journal = Maturitas | volume = 61 | issue = 1-2 | pages = 171–80 | date = 2008 | pmid = 19434889 | doi = | url = }} 3. ^1 {{cite journal | vauthors = Vij U, Murugesan K, Kalita JC, Farooq A | title = Interaction of antiprogestins with progesterone receptors in rat uterus | journal = J. Steroid Biochem. | volume = 32 | issue = 2 | pages = 279–82 | date = February 1989 | pmid = 2921869 | doi = | url = }} 4. ^1 2 {{cite journal | vauthors = García-Becerra R, Borja-Cacho E, Cooney AJ, Jackson KJ, Lemus AE, Pérez-Palacios G, Larrea F | title = The intrinsic transcriptional estrogenic activity of a non-phenolic derivative of levonorgestrel is mediated via the estrogen receptor-alpha | journal = J. Steroid Biochem. Mol. Biol. | volume = 82 | issue = 4-5 | pages = 333–41 | date = November 2002 | pmid = 12589940 | doi = | url = }} 5. ^{{cite journal | vauthors = Chu YH, Li QA, Zhao ZF, Zhou YP, Cao DC | title = [Antiprogestational action of 5 alpha-dihydronorethisterone] | language = Chinese | journal = Zhongguo Yao Li Xue Bao | volume = 6 | issue = 2 | pages = 125–9 | year = 1985 | pmid = 2934946 | doi = | url = }} 6. ^1 {{cite journal | vauthors = Cabeza M, Vilchis F, Lemus AE, Díaz de León L, Pérez-Palacios G | title = Molecular interactions of levonorgestrel and its 5 alpha-reduced derivative with androgen receptors in hamster flanking organs | journal = Steroids | volume = 60 | issue = 9 | pages = 630–5 | date = September 1995 | pmid = 8545853 | doi = 10.1016/0039-128X(95)00075-2 | url = }} 7. ^{{cite journal | vauthors = Khan FS, Fotherby K | title = In vitro metabolism of 17 alpha-ethynylsteroids | journal = J. Steroid Biochem. | volume = 10 | issue = 4 | pages = 437–42 | date = April 1979 | pmid = 449320 | doi = | url = }} 8. ^1 {{cite journal | vauthors = Santillán R, Pérez-Palacios G, Reyes M, Damián-Matsumura P, García GA, Grillasca I, Lemus AE | title = Assessment of the oestrogenic activity of the contraceptive progestin levonorgestrel and its non-phenolic metabolites | journal = Eur. J. Pharmacol. | volume = 427 | issue = 2 | pages = 167–74 | date = September 2001 | pmid = 11557270 | doi = 10.1016/S0014-2999(01)01263-8 | url = }} 10 : 5α-Reduced steroid metabolites|Alcohols|Alkynes|Androgens and anabolic steroids|Enantiopure drugs|Estranes|Human drug metabolites|Ketones|Selective progesterone receptor modulators|Synthetic estrogens |
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