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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
Structure of MORPHINE-3-GLUCURONIDE

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

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
Lack of effect of ondansetron on the pharmacokinetics and analgesic effects of morphine and metabolites after single-dose morphine administration in healthy volunteers.
2001 Apr
Pharmacokinetics of morphine and its glucuronidated metabolites in burn injuries.
2001 Dec
Pharmacokinetics of morphine 3-esters after oral administration in rabbits.
2001 Jun
Hydromorphone-3-glucuronide: a more potent neuro-excitant than its structural analogue, morphine-3-glucuronide.
2001 Jun 15
Epirubicin glucuronidation is catalyzed by human UDP-glucuronosyltransferase 2B7.
2001 May
Simultaneous expression of guinea pig UDP-glucuronosyltransferase 2B21 and 2B22 in COS-7 cells enhances UDP-glucuronosyltransferase 2B21-catalyzed morphine-6-glucuronide formation.
2001 Nov
Ethnicity influences morphine pharmacokinetics and pharmacodynamics.
2001 Oct
LC determination of morphine and morphine glucuronides in human plasma by coulometric and UV detection.
2001 Sep
Interaction of morphine, fentanyl, sufentanil, alfentanil, and loperamide with the efflux drug transporter P-glycoprotein.
2002 Apr
Quantitative gas chromatographic/mass spectrometric analysis of morphine glucuronides in human plasma by negative ion chemical ionization mass spectrometry.
2002 Apr
Intranasal delivery of morphine.
2002 Apr
Pharmacokinetic evaluation of a sprinkle-dose regimen of a once-daily, extended-release morphine formulation.
2002 Feb
Increased plasma morphine metabolites in terminally ill cancer patients with delirium: an intra-individual comparison.
2002 Feb
Diclofenac does not interact with codeine metabolism in vivo: a study in healthy volunteers.
2002 Feb 27
Sex-specific differences in levels of morphine, morphine-3-glucuronide, and morphine antinociception in rats.
2002 Jan
An automatic 96-well solid phase extraction and liquid chromatography-tandem mass spectrometry method for the analysis of morphine, morphine-3-glucuronide and morphine-6-glucuronide in human plasma.
2002 Jan 1
Pain, sedation and morphine metabolism in cancer patients during long-term treatment with sustained-release morphine.
2002 Mar
Cloning and characterisation of the first drug-metabolising canine UDP-glucuronosyltransferase of the 2B subfamily.
2003 Apr 15
The study of codeine-gluthetimide pharmacokinetic interaction in rats.
2003 Aug 8
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
Relationships among morphine metabolism, pain and side effects during long-term treatment: an update.
2003 Jan
[Development of opioid tolerance -- molecular mechanisms and clinical consequences].
2003 Jan
Influences on serum concentrations of morphine, M6G and M3G during routine clinical drug monitoring: a prospective survey in 300 adult cancer patients.
2003 Jul
The pharmacokinetics of the interstitial space in humans.
2003 Jul 30
A pharmacogenetic study of uridine diphosphate-glucuronosyltransferase 2B7 in patients receiving morphine.
2003 Jun
Production of a recombinant anti-morphine-3-glucuronide single-chain variable fragment (scFv) antibody for the development of a "real-time" biosensor-based immunoassay.
2003 May 1
The neuroexcitatory morphine metabolite, morphine-3-glucuronide (M3G), is not neurotoxic in primary cultures of either hippocampal or cerebellar granule neurones.
2003 Oct
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
Metabolism of opioids is altered in liver microsomes of sickle cell transgenic mice.
2004 Jan
Effects of perioperative oral amantadine on postoperative pain and morphine consumption in patients after radical prostatectomy: results of a preliminary study.
2004 Jan
Pharmacological consequences of long-term morphine treatment in patients with cancer and chronic non-malignant pain.
2004 Jun
The bioavailability of morphine applied topically to cutaneous ulcers.
2004 May
Simultaneous measurement and integrated analysis of analgesia and respiration after an intravenous morphine infusion.
2004 Nov
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
Mechanisms of nociception evoked by intrathecal high-dose morphine.
2005 Oct
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:24:09 GMT 2023
Edited
by admin
on Fri Dec 15 15:24:09 GMT 2023
Record UNII
O27Z9CH39A
Record Status Validated (UNII)
Record Version
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Name Type Language
MORPHINE-3-GLUCURONIDE
Common Name English
MORPHINE 3-O-.BETA.-D-GLUCURONIDE
Common Name English
.BETA.-D-GLUCOPYRANOSIDURONIC ACID
Common Name English
.BETA.-D-GLUCOPYRANOSIDURONIC ACID, (5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-6-HYDROXY-17-METHYLMORPHINAN-3-YL
Systematic Name English
GLUCOPYRANOSIDURONIC ACID, MORPHINE-3, .BETA.-D-
Common Name English
Code System Code Type Description
WIKIPEDIA
MORPHINE-3-GLUCURONIDE
Created by admin on Fri Dec 15 15:24:09 GMT 2023 , Edited by admin on Fri Dec 15 15:24:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID80174157
Created by admin on Fri Dec 15 15:24:09 GMT 2023 , Edited by admin on Fri Dec 15 15:24:09 GMT 2023
PRIMARY
FDA UNII
O27Z9CH39A
Created by admin on Fri Dec 15 15:24:09 GMT 2023 , Edited by admin on Fri Dec 15 15:24:09 GMT 2023
PRIMARY
CAS
20290-09-9
Created by admin on Fri Dec 15 15:24:09 GMT 2023 , Edited by admin on Fri Dec 15 15:24:09 GMT 2023
PRIMARY
PUBCHEM
5484731
Created by admin on Fri Dec 15 15:24:09 GMT 2023 , Edited by admin on Fri Dec 15 15:24:09 GMT 2023
PRIMARY
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