Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H27NO9 |
| Molecular Weight | 461.4618 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4O[C@@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)C(O)=O
InChI
InChIKey=WAEXKFONHRHFBZ-ZXDZBKESSA-N
InChI=1S/C23H27NO9/c1-24-7-6-23-10-3-4-12(25)20(23)32-18-13(5-2-9(14(18)23)8-11(10)24)31-22-17(28)15(26)16(27)19(33-22)21(29)30/h2-5,10-12,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11+,12-,15-,16-,17+,19-,20-,22+,23-/m0/s1
| Molecular Formula | C23H27NO9 |
| Molecular Weight | 461.4618 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Interindividual variation in the ratio between plasma morphine and its metabolites in cancer patients. | 2003 |
|
| Morphine-3-glucuronide's neuro-excitatory effects are mediated via indirect activation of N-methyl-D-aspartic acid receptors: mechanistic studies in embryonic cultured hippocampal neurones. | 2003 Aug |
|
| In search of a role for the morphine metabolite morphine-3-glucuronide. | 2003 Aug |
|
| Routine drug monitoring of serum concentrations of morphine, morphine-3-glucuronide and morphine-6-glucuronide do not predict clinical observations in cancer patients. | 2003 Dec |
|
| The oral-to-intravenous equianalgesic ratio of morphine based on plasma concentrations of morphine and metabolites in advanced cancer patients receiving chronic morphine treatment. | 2003 Dec |
|
| Influences on serum concentrations of morphine, M6G and M3G during routine clinical drug monitoring: a prospective survey in 300 adult cancer patients. | 2003 Jul |
|
| A novel metabolic pathway of morphine: formation of morphine glucosides in cancer patients. | 2003 Jun |
|
| Age- and therapy-related effects on morphine requirements and plasma concentrations of morphine and its metabolites in postoperative infants. | 2003 May |
|
| Repeated exposures to heroin and/or cadmium alter the rate of formation of morphine glucuronides in the rat. | 2003 Nov |
|
| High levels of morphine-6-glucuronide in street heroin addicts. | 2003 Nov |
|
| The neuroexcitatory morphine metabolite, morphine-3-glucuronide (M3G), is not neurotoxic in primary cultures of either hippocampal or cerebellar granule neurones. | 2003 Oct |
|
| Pharmacokinetics of high doses of intramuscular and oral heroin in narcotic addicts. | 2003 Oct |
|
| Interpretation of the presence of 6-monoacetylmorphine in the absence of morphine-3-glucuronide in urine samples: evidence of heroin abuse. | 2003 Oct |
|
| Bioavailability of a morphine suppository is increased after intracolostomal administration in colostoma-constructed rabbits. | 2003 Oct 20 |
|
| Determination of morphine and morphine glucuronides in human plasma by 96-well plate solid-phase extraction and liquid chromatography-electrospray ionization mass spectrometry. | 2003 Oct 25 |
|
| Isoform selectivity and kinetics of morphine 3- and 6-glucuronidation by human udp-glucuronosyltransferases: evidence for atypical glucuronidation kinetics by UGT2B7. | 2003 Sep |
|
| Development and validation of a liquid chromatography-mass spectrometry assay for the determination of opiates and cocaine in meconium. | 2003 Sep 5 |
|
| Developmental pharmacokinetics of morphine and its metabolites in neonates, infants and young children. | 2004 Feb |
|
| A highly toxic morphine-3-glucuronide derivative. | 2004 Feb 23 |
|
| Pharmacological consequences of long-term morphine treatment in patients with cancer and chronic non-malignant pain. | 2004 Jun |
|
| A novel functional polymorphism in the uridine diphosphate-glucuronosyltransferase 2B7 promoter with significant impact on promoter activity. | 2004 Mar |
|
| The bioavailability of morphine applied topically to cutaneous ulcers. | 2004 May |
|
| Comparison of the antinociceptive effect of morphine, methadone, buprenorphine and codeine in two substrains of Sprague-Dawley rats. | 2004 May 10 |
|
| Determination of morphine, morphine-3-glucuronide and morphine-6-glucuronide in monkey and dog plasma by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. | 2004 May 28 |
|
| Simultaneous measurement and integrated analysis of analgesia and respiration after an intravenous morphine infusion. | 2004 Nov |
|
| The 118 A > G polymorphism in the human mu-opioid receptor gene may increase morphine requirements in patients with pain caused by malignant disease. | 2004 Nov |
|
| Validated assay for the determination of markers of illicit heroin in urine samples for the control of patients in a heroin prescription program. | 2004 Nov 5 |
|
| Day-to-day variations during clinical drug monitoring of morphine, morphine-3-glucuronide and morphine-6-glucuronide serum concentrations in cancer patients. A prospective observational study. | 2004 Oct 4 |
|
| On-line desalting and determination of morphine, morphine-3-glucuronide and morphine-6-glucuronide in microdialysis and plasma samples using column switching and liquid chromatography/tandem mass spectrometry. | 2005 |
|
| Transfer of morphine along the olfactory pathway to the central nervous system after nasal administration to rodents. | 2005 Apr |
|
| Is morphine-3-glucuronide of therapeutic relevance? | 2005 Aug |
|
| Effects of morphine and its metabolites on immune function in advanced cancer patients. | 2005 Dec |
|
| Novel assay format permitting the prolonged use of regeneration-based sensor chip technology. | 2005 Jan |
|
| The contribution of fetal metabolism to the disposition of morphine. | 2005 Jan |
|
| Simultaneous determination of morphine, oxycodone, morphine-3-glucuronide, and noroxycodone concentrations in rat serum by high performance liquid chromatography-electrospray ionization-tandem mass spectrometry. | 2005 Jan 25 |
|
| Age-dependent morphine tolerance development in the rat. | 2005 Jun |
|
| Modulation of UDP-glucuronosyltransferase function by cytochrome P450: evidence for the alteration of UGT2B7-catalyzed glucuronidation of morphine by CYP3A4. | 2005 Mar |
|
| HPLC with laser-induced native fluorescence detection for morphine and morphine glucuronides from blood after immunoaffinity extraction. | 2005 May |
|
| LC-ESI-MS/MS analysis for the quantification of morphine, codeine, morphine-3-beta-D-glucuronide, morphine-6-beta-D-glucuronide, and codeine-6-beta-D-glucuronide in human urine. | 2005 Nov |
|
| Modulation of UDP-glucuronosyltransferase 2B7 function by cytochrome P450s in vitro: differential effects of CYP1A2, CYP2C9 and CYP3A4. | 2005 Oct |
|
| Effect of repeated administrations of heroin, naltrexone, methadone, and alcohol on morphine glucuronidation in the rat. | 2005 Oct |
|
| Mechanisms of nociception evoked by intrathecal high-dose morphine. | 2005 Oct |
|
| Development and validation of a radioreceptor assay for the determination of morphine and its active metabolites in serum. | 2005 Oct 4 |
|
| Fetal morphine metabolism and clearance are constant during late gestation. | 2006 Apr |
|
| Optimizing recombinant antibody function in SPR immunosensing. The influence of antibody structural format and chip surface chemistry on assay sensitivity. | 2006 Aug 15 |
|
| Morphine hyperalgesia in mice is unrelated to opioid activity, analgesia, or tolerance: evidence for multiple diverse hyperalgesic systems. | 2006 Jan 27 |
|
| Direct nose-to-brain transfer of morphine after nasal administration to rats. | 2006 Mar |
|
| Differential in vitro inhibition of M3G and M6G formation from morphine by (R)- and (S)-methadone and structurally related opioids. | 2006 Mar |
|
| An automated and fully validated LC-MS/MS procedure for the simultaneous determination of 11 opioids used in palliative care, with 5 of their metabolites. | 2006 May |
|
| Transport is not rate-limiting in morphine glucuronidation in the single-pass perfused rat liver preparation. | 2006 May |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:24:09 UTC 2023
by
admin
on
Fri Dec 15 15:24:09 UTC 2023
|
| Record UNII |
O27Z9CH39A
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
MORPHINE-3-GLUCURONIDE
Created by
admin on Fri Dec 15 15:24:09 UTC 2023 , Edited by admin on Fri Dec 15 15:24:09 UTC 2023
|
PRIMARY | |||
|
DTXSID80174157
Created by
admin on Fri Dec 15 15:24:09 UTC 2023 , Edited by admin on Fri Dec 15 15:24:09 UTC 2023
|
PRIMARY | |||
|
O27Z9CH39A
Created by
admin on Fri Dec 15 15:24:09 UTC 2023 , Edited by admin on Fri Dec 15 15:24:09 UTC 2023
|
PRIMARY | |||
|
20290-09-9
Created by
admin on Fri Dec 15 15:24:09 UTC 2023 , Edited by admin on Fri Dec 15 15:24:09 UTC 2023
|
PRIMARY | |||
|
5484731
Created by
admin on Fri Dec 15 15:24:09 UTC 2023 , Edited by admin on Fri Dec 15 15:24:09 UTC 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> METABOLITE |
|
||
|
PARENT -> METABOLITE INACTIVE |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
|
