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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-6-GLUCURONIDE

SMILES

[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])C=C[C@@H]2O[C@]6([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)C(O)=O)=CC=C3O

InChI

InChIKey=GNJCUHZOSOYIEC-GAROZEBRSA-N
InChI=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

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

Morphine-6-glucuronide is a pharmacologically active metabolite of morphine that is being developed by CeNeS Pharmaceuticals as an alternative to morphine for the management of postoperative pain. Compared to morphine, Morphine-6-glucuronide has been reported to have6 and 86 times lower affinity for the human mu and kappa opioid receptors, respectively, and similar affinity for the delta opioid receptor. Morphine-6-glucuronide is was studied in phase III clinical trials for postoperative pain management. Unfortunately, Morphine-6-glucuronide failed to demonstrate superior safety compared to Morphine and further development was discontinued. Morphine-6-glucuronide accumulates after administration of morphine to patients with renal insufficiency, and analgesia can be obtained with lower doses of morphine compared to patients with normal renal function. More importantly, the dose should be reduced to avoid serious side-effects, although the simulations in this review did not account for side-effects.

Approval Year

PubMed

PubMed

TitleDatePubMed
Identifying potential binding modes and explaining partitioning behavior using flexible alignments and multidimensional scaling.
2001 Dec
Pharmacokinetics of morphine and its glucuronidated metabolites in burn injuries.
2001 Dec
The transfer half-life of morphine-6-glucuronide from plasma to effect site assessed by pupil size measurement in healthy volunteers.
2001 Dec
Limited phase I study of morphine-3-glucuronide.
2001 Nov
Ultrafast liquid chromatography/tandem mass spectrometry bioanalysis of polar analytes using packed silica columns.
2002
Dracunculus medinensis and Schistosoma mansoni contain opiate alkaloids.
2002 Apr
The bioavailability and pharmacokinetics of subcutaneous, nebulized and oral morphine-6-glucuronide.
2002 Apr
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
Verapamil decreases glucuronidase activity in the gut.
2002 Apr 15
Pharmacokinetic modeling to predict morphine and morphine-6-glucuronide plasma concentrations in healthy young volunteers.
2002 Aug
Morphine glucuronide-to-morphine plasma ratios are unaffected by the UGT2B7 H268Y and UGT1A1*28 polymorphisms in cancer patients on chronic morphine therapy.
2002 Aug
The influence of inhibition of probenecid sensitive transporters on the central nervous system (CNS) uptake and the antinociceptive activity of morphine-6-glucuronide in rats.
2002 Aug 30
Unwanted effects of morphine-6-glucoronide and morphine.
2002 Dec
Pharmacogenetics of codeine metabolism in an urban population of children and its implications for analgesic reliability.
2002 Dec
Pharmacokinetic evaluation of a sprinkle-dose regimen of a once-daily, extended-release morphine formulation.
2002 Feb
Changing M3G/M6G ratios and pharmacodynamics in a cancer patient during long-term morphine treatment.
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
Cold stress alters Mytilus edulis pedal ganglia expression of mu opiate receptor transcripts determined by real-time RT-PCR and morphine levels.
2002 Feb 28
A phase I/II study of nebulized morphine-6-glucuronide in patients with cancer-related breathlessness.
2002 Jan
Morphine in cancer pain management: a practical guide.
2002 Jan
The polymorphism A118G of the human mu-opioid receptor gene decreases the pupil constrictory effect of morphine-6-glucuronide but not that of morphine.
2002 Jan
A polymorphism (A118G) in the mu-opioid receptor gene affects the response to morphine-6-glucuronide in humans.
2002 Jan
Colostrum morphine concentrations during postcesarean intravenous patient-controlled analgesia.
2002 Jan
Pain, sedation and morphine metabolism in cancer patients during long-term treatment with sustained-release morphine.
2002 Mar
Morphine 6 glucuronide stimulates nitric oxide release in mussel neural tissues: evidence for a morphine 6 glucuronide opiate receptor subtype.
2002 Mar
Differential antagonism of endomorphin-1 and endomorphin-2 supraspinal antinociception by naloxonazine and 3-methylnaltrexone.
2002 May
Contribution of morphine-6-glucuronide to antinociception following intravenous administration of morphine to healthy volunteers.
2002 May
Pharmacokinetic differences of morphine and morphine-glucuronides are reflected in locomotor activity.
2002 Nov
Increased CNS uptake and enhanced antinociception of morphine-6-glucuronide in rats after inhibition of P-glycoprotein.
2002 Oct
Randomized, double-blind, placebo-controlled study of the effect of rectal paracetamol on morphine consumption after abdominal hysterectomy.
2003 Apr
Rapid and simple method to determine morphine and its metabolites in rat plasma by liquid chromatography-mass spectrometry.
2003 Apr 25
Gateways to clinical trials.
2003 Dec
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 novel metabolic pathway of morphine: formation of morphine glucosides in cancer patients.
2003 Jun
A pharmacogenetic study of uridine diphosphate-glucuronosyltransferase 2B7 in patients receiving morphine.
2003 Jun
Plasma concentrations of morphine, morphine-6-glucuronide and morphine-3-glucuronide and their relationship with analgesia and side effects in patients with cancer-related pain.
2003 Mar
Encapsulation of an intrathecal catheter.
2003 May
Age- and therapy-related effects on morphine requirements and plasma concentrations of morphine and its metabolites in postoperative infants.
2003 May
High levels of morphine-6-glucuronide in street heroin addicts.
2003 Nov
Different distribution of morphine and morphine-6 beta-glucuronide after intracerebroventricular injection in rats.
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
Pharmacokinetic-pharmacodynamic modeling of morphine-6-glucuronide-induced analgesia in healthy volunteers: absence of sex differences.
2004 Jan
Patents
Substance Class Chemical
Created
by admin
on Thu Jul 06 23:20:39 UTC 2023
Edited
by admin
on Thu Jul 06 23:20:39 UTC 2023
Record UNII
64Y9KYM60R
Record Status Validated (UNII)
Record Version
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Name Type Language
MORPHINE-6-GLUCURONIDE
Common Name English
MORPHINE 6-GLUCURONIDE
Common Name English
MORPHINE 6-.BETA.-D-GLUCURONIDE
Common Name English
MORPHINE GLUCURONIDE
INN  
INN  
Official Name English
.BETA.-D-GLUCOPYRANOSIDURONIC ACID, (5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-3-HYDROXY-17-METHYLMORPHINAN-6-YL
Systematic Name English
morphine glucuronide [INN]
Common Name English
MORPHINE GLUCURONIDE, (-)-
Common Name English
Code System Code Type Description
SMS_ID
100000143116
Created by admin on Thu Jul 06 23:20:40 UTC 2023 , Edited by admin on Thu Jul 06 23:20:40 UTC 2023
PRIMARY
EVMPD
SUB118806
Created by admin on Thu Jul 06 23:20:40 UTC 2023 , Edited by admin on Thu Jul 06 23:20:40 UTC 2023
PRIMARY
NCI_THESAURUS
C166899
Created by admin on Thu Jul 06 23:20:40 UTC 2023 , Edited by admin on Thu Jul 06 23:20:40 UTC 2023
PRIMARY
DRUG BANK
DB06409
Created by admin on Thu Jul 06 23:20:40 UTC 2023 , Edited by admin on Thu Jul 06 23:20:40 UTC 2023
PRIMARY
FDA UNII
64Y9KYM60R
Created by admin on Thu Jul 06 23:20:40 UTC 2023 , Edited by admin on Thu Jul 06 23:20:40 UTC 2023
PRIMARY
PUBCHEM
5360621
Created by admin on Thu Jul 06 23:20:40 UTC 2023 , Edited by admin on Thu Jul 06 23:20:40 UTC 2023
PRIMARY
ChEMBL
CHEMBL611421
Created by admin on Thu Jul 06 23:20:40 UTC 2023 , Edited by admin on Thu Jul 06 23:20:40 UTC 2023
PRIMARY
WIKIPEDIA
MORPHINE-6-GLUCURONIDE
Created by admin on Thu Jul 06 23:20:40 UTC 2023 , Edited by admin on Thu Jul 06 23:20:40 UTC 2023
PRIMARY
EPA CompTox
DTXSID40174158
Created by admin on Thu Jul 06 23:20:40 UTC 2023 , Edited by admin on Thu Jul 06 23:20:40 UTC 2023
PRIMARY
CAS
20290-10-2
Created by admin on Thu Jul 06 23:20:40 UTC 2023 , Edited by admin on Thu Jul 06 23:20:40 UTC 2023
PRIMARY
INN
8377
Created by admin on Thu Jul 06 23:20:40 UTC 2023 , Edited by admin on Thu Jul 06 23:20:40 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
BINDER->LIGAND
SOLVATE->ANHYDROUS
METABOLIC ENZYME -> SUBSTRATE
TARGET -> AGONIST
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PARENT -> METABOLITE ACTIVE
MAJOR
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ACTIVE MOIETY