| 词条 | Morphine-6-glucuronide |
| 释义 |
| Verifiedfields = changed | verifiedrevid = 460765087 | ImageFile=Morphine-6-glucuronide2DCSD.svg | ImageSize=200px | IUPACName= | OtherNames=M6G |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4514548 | InChI = 1/C23H27NO9/c1-24-7-6-23-10-3-5-13(31-22-17(28)15(26)16(27)19(33-22)21(29)30)20(23)32-18-12(25)4-2-9(14(18)23)8-11(10)24/h2-5,10-11,13,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11+,13-,15-,16-,17+,19-,20-,22+,23-/m0/s1 | InChIKey = GNJCUHZOSOYIEC-GAROZEBRBC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C23H27NO9/c1-24-7-6-23-10-3-5-13(31-22-17(28)15(26)16(27)19(33-22)21(29)30)20(23)32-18-12(25)4-2-9(14(18)23)8-11(10)24/h2-5,10-11,13,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11+,13-,15-,16-,17+,19-,20-,22+,23-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = GNJCUHZOSOYIEC-GAROZEBRSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo=20290-10-2 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1330 | PubChem=5360621 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = 64Y9KYM60R | SMILES = O=C(O)[C@H]6O[C@@H](O[C@H]1/C=C\\[C@@H]5[C@@]24c3c(ccc(O)c3O[C@@H]12)C[C@H]5N(C)CC4)[C@H](O)[C@@H](O)[C@@H]6O | MeSHName=Morphine-6-glucuronide |Section2={{Chembox Properties | Formula=C23H27NO9 | MolarMass=461.46 g/mol | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }}Morphine-6-glucuronide (M6G) is a major active metabolite of morphine, and as such is the molecule responsible for much of the pain-relieving effects of morphine and heroin.{{Citation needed|date=October 2015}} M6G is formed from morphine by the enzyme UGT2B7.[1] It has analgesic effects more potent than morphine.[2] M6G can accumulate to toxic levels in kidney failure.[3][4] History of discoveryThis analgesic activity of M6G (in animals) was first noted by Yoshimura.[3] Subsequent work at St Bartholomew's Hospital, London in the 1980s,[4] using a sensitive and specific HPLC assay,[5] accurately defined for the first time the metabolism of morphine, and the abundance of this metabolite (along with morphine-3-glucuronide,[6] considered an inactive metabolite). It was postulated that kidney impairment would result in accumulation of the kidney-excreted active agent M6G, leading to potentially fatal toxicity such as respiratory depression. The frequent use of morphine in critically ill patients, and the common occurrence of kidney failure in this group implied that M6G accumulation could be a common, but previously unanticipated problem. The first studies demonstrated massive levels of M6G in 3 patients with renal failure, which resolved as kidney function returned.[7] Accumulation of M3G and M6G also decrease with return of kidney function after kidney transplantation.[8] A key step in defining the importance of M6G in humans came in 1992 when the substance was artificially synthesised and administered to patients with pain, the majority of whom described pain relief.[9] See also
References1. ^{{cite journal | vauthors = Coffman BL, Rios GR, King CD, Tephly TR | title = Human UGT2B7 catalyzes morphine glucuronidation | journal = Drug Metab. Dispos. | volume = 25 | issue = 1 | pages = 1–4 | date = 1 January 1997 | pmid = 9010622 | url = http://dmd.aspetjournals.org/cgi/content/abstract/25/1/1 }} {{Opioidergics}}2. ^{{cite journal | vauthors = van Dorp EL, Romberg R, Sarton E, Bovill JG, Dahan A | title = Morphine-6-glucuronide: morphine's successor for postoperative pain relief? | journal = Anesthesia and Analgesia | volume = 102 | issue = 6 | pages = 1789–1797 | year = 2006 | pmid = 16717327 | doi = 10.1213/01.ane.0000217197.96784.c3 | url = http://www.anesthesia-analgesia.org/cgi/content/full/102/6/1789 }} 3. ^{{cite journal | title = Metabolism of drugs. LXII. Isolation and identification of morphine glucuronides in urine and bile of rabbits | journal = Biochem Pharmacol | year = 1969 | volume = 18 | pages = 279–86 | doi = 10.1016/0006-2952(69)90205-6 | author = Hidetoshi, Y | pmid = 5778147 | last2 = Oguri | first2 = K | last3 = Tsukamoto | first3 = H | issue = 2}} 4. ^{{Cite journal | doi = 10.1038/clpt.1990.2 | title = Morphine and metabolite behavior after different routes of morphine administration: demonstration of the importance of the active metabolite morphine-6-glucuronide | journal = Clin Pharmacol Ther | year = 1990 | volume = 47 | pages = 12–9 | pmid = 2295214 | last1 = Osborne | first1 = R | last2 = Joel | first2 = S | last3 = Trew | first3 = D | last4 = Slevin | first4 = M | issue = 1}} 5. ^{{cite journal | title = An improved method for the simultaneous determination of morphine and its principal glucuronide metabolites| journal = J Chromatogr| year = 1988 | volume = 430 | pages = 394–9 | doi = 10.1016/S0378-4347(00)83176-X | author = Joel, S | pmid = 3235512 | last2 = Osborne | first2 = RJ | last3 = Slevin | first3 = ML | issue = 2}} 6. ^Renal tubular transport of morphine, morphine-6-glucuronide, and morphine-3-glucuronide in the isolated perfused rat kidney. JT Van Crugten, BC Sallustio, RL Nation and AA Somogyi. Department of Clinical and Experimental Pharmacology, University of Adelaide, Australia. 7. ^1 {{cite journal | title = Morphine intoxication in renal failure: the role of morphine-6-glucuronide | journal = Br Med J | year = 1986 | volume = 292 | pages = 1548–9 | doi = 10.1136/bmj.292.6535.1548 | author = Osborne, R J | pmid = 3087512 | last2 = Joel | first2 = SP | last3 = Slevin | first3 = ML | issue = 6535 | pmc = 1340555}} 8. ^1 {{cite journal | doi = 10.1038/clpt.1993.127 | title = The pharmacokinetics of morphine and morphine glucuronides in kidney failure | journal = Clin Pharmacol Ther | year = 1993 | volume = 54 | pages = 158–67 | pmid = 8354025 | last1 = Osborne | first1 = R | last2 = Joel | first2 = S | last3 = Grebenik | first3 = K | last4 = Trew | first4 = D | last5 = Slevin | first5 = M | issue = 2}} 9. ^{{cite journal | title = The analgesic activity of morphine-6-glucuronide | journal = Br J Clin Pharmacol | year = 1992 | volume = 34 | pages = 130–8 | pmid = 1419474 | last1 = Osborne | first1 = R | last2 = Thompson | first2 = P | last3 = Joel | first3 = S | last4 = Trew | first4 = D | last5 = Patel | first5 = N | last6 = Slevin | first6 = M | issue = 2 | pmc = 1381529 | doi = 10.1111/j.1365-2125.1992.tb04121.x }} 5 : Mu-opioid agonists|Opioid metabolites|Morphinans|Glucuronides|Phenols |
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