| 词条 | Buprenorphine-3-glucuronide |
| 释义 |
| IUPAC_name = (5α,6β,14β,18R)-17-(Cyclopropylmethyl)-18-[(2S)-2-hydroxy-3,3-dimethyl-2-butanyl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-2-yl β-D-glucopyranosiduronic acid | image = Buprenorphine-3-glucuronide.svg | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 101224-22-0 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = L7FYM9GI97 | ATC_prefix = None | ATC_suffix = | PubChem = 127780 | DrugBank = | ChemSpiderID = 113341 | chemical_formula = | C=35 | H=49 | N=1 | O=10 | molecular_weight = 643.764 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)CC8CC8)OC)(C(C)(C)C)O | StdInChI = 1S/C35H49NO10/c1-31(2,3)32(4,42)20-15-33-10-11-35(20,43-5)30-34(33)12-13-36(16-17-6-7-17)21(33)14-18-8-9-19(26(46-30)22(18)34)44-29-25(39)23(37)24(38)27(45-29)28(40)41/h8-9,17,20-21,23-25,27,29-30,37-39,42H,6-7,10-16H2,1-5H3,(H,40,41)/t20-,21-,23+,24+,25-,27+,29-,30-,32+,33-,34+,35-/m1/s1 | StdInChIKey = CZULHKGIAJASAA-WWIHBJMFSA-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 = }}Buprenorphine-3-glucuronide (B3G) is a major active metabolite of the opioid modulator buprenorphine.[1] It has affinity for the μ-opioid receptor (Ki = 4.9 (± 2.7) pM), δ-opioid receptor (Ki = 270 nM), and nociceptin receptor (Ki = 36 μM), but not for the κ-opioid receptor.[1] Whether B3G acts as an agonist or antagonist of each of the former three respective sites has yet to be determined.[2] In rats, at the doses assayed, B3G has been found to produce a small degree of antinociception, and similarly to buprenorphine in these assays, has not been found to produce sedation, reduce locomotion, or decrease respiratory rate.[1] Of all of the active metabolites of buprenorphine, B3G is thought to be the most similar to the parent drug.[1] Unlike norbuprenorphine, but similarly to buprenorphine (and norbuprenorphine-3-glucuronide), B3G is not a substrate for P-glycoprotein, and hence may cross the blood-brain-barrier significantly.[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 {{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 : Mu-opioid agonists|Opioid metabolites|Morphinans|Phenols|Alcohols|Ethers|Oripavines|Glucuronides |
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