| 词条 | Norbuprenorphine-3-glucuronide |
| 释义 |
| IUPAC_name = (5β,7β)-7-[(2R)-2-Hydroxy-3,3-dimethyl-2-butanyl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-yl (5ξ)-β-D-lyxo-hexopyranosiduronic acid | image = Norbuprenorphine-3-glucuronide.svg | CAS_number = 469887-29-4 | ATC_prefix = None | ATC_suffix = | PubChem = 46782577 | DrugBank = | chemical_formula = | C=31 | H=43 | N=1 | O=10 | molecular_weight = 589.674 g/mol | SMILES = C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN[C@@H]3Cc6c5c(c(cc6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O)O4)OC)(C(C)(C)C)O | ChemSpiderID = 35517741 | StdInChI = 1S/C31H43NO10/c1-27(2,3)28(4,38)16-13-29-8-9-31(16,39-5)26-30(29)10-11-32-17(29)12-14-6-7-15(22(42-26)18(14)30)40-25-21(35)19(33)20(34)23(41-25)24(36)37/h6-7,16-17,19-21,23,25-26,32-35,38H,8-13H2,1-5H3,(H,36,37)/t16-,17-,19+,20+,21-,23+,25-,26-,28+,29-,30+,31-/m1/s1 | StdInChIKey = OOLGGESLZHGXGC-TXYLTYGDSA-N | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | pregnancy_AU = | pregnancy_US = | pregnancy_category= | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = }}Norbuprenorphine-3-glucuronide (N3G) is a major active metabolite of the opioid modulator buprenorphine.[1] It has affinity for the κ-opioid receptor (Ki = 300 nM) and the nociceptin receptor (Ki = 18 μM), but not for the μ- or δ-opioid receptors.[1] Whether N3G acts as an agonist or antagonist of each of the former two respective sites has yet to be determined.[2] In animals, N3G has been found to produce sedation, decreased locomotion, and a small amount of antinociception, properties which are consistent with the effects of κ-opioid receptor agonists.[1] In addition, N3G has been found to reduce tidal volume but not respiratory rate.[1] Unlike norbuprenorphine, but similarly to buprenorphine and buprenorphine-3-glucuronide, N3G is not a substrate for P-glycoprotein.[2] However, due to its highly hydrophilic nature, N3G nonetheless passes the blood-brain-barrier in only very small amounts.[2] See also
References1. ^1 2 3 {{cite journal |vauthors=Brown SM, Holtzman M, Kim T, Kharasch ED | title = Buprenorphine metabolites, buprenorphine-3-glucuronide and norbuprenorphine-3-glucuronide, are biologically active | journal = Anesthesiology | volume = 115 | issue = 6 | pages = 1251–60 |date=December 2011 | pmid = 22037640 | pmc = 3560935 | doi = 10.1097/ALN.0b013e318238fea0 | url = http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0003-3022&volume=115&issue=6&spage=1251}} {{Opioidergics}}{{nervous-system-drug-stub}}2. ^1 2 {{cite journal |vauthors=Brown SM, Campbell SD, Crafford A, Regina KJ, Holtzman MJ, Kharasch ED | title = P-glycoprotein is a major determinant of norbuprenorphine brain exposure and antinociception | journal = J. Pharmacol. Exp. Ther. | volume = 343 | issue = 1 | pages = 53–61 |date=October 2012 | pmid = 22739506 | pmc = 3464040 | doi = 10.1124/jpet.112.193433 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=22739506}} 8 : Morphinans|Phenols|Alcohols|Ethers|Glucuronides|Kappa agonists|Opioid metabolites|Peripherally selective drugs |
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