U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
The transfer half-life of morphine-6-glucuronide from plasma to effect site assessed by pupil size measurement in healthy volunteers.
2001 Dec
Pharmacokinetics of morphine 3-esters after oral administration in rabbits.
2001 Jun
Hydrophobic forms of morphine-6-glucosides.
2001 Jun 4
Morphine-6 beta-glucuronide induces potent immunomodulation.
2001 May
Epirubicin glucuronidation is catalyzed by human UDP-glucuronosyltransferase 2B7.
2001 May
Limited sampling approach.
2001 Nov
Morphine-6beta-glucuronide and morphine-3-glucuronide, opioid receptor agonists with different potencies.
2001 Nov 1
Ethnicity influences morphine pharmacokinetics and pharmacodynamics.
2001 Oct
Dracunculus medinensis and Schistosoma mansoni contain opiate alkaloids.
2002 Apr
Quantitative gas chromatographic/mass spectrometric analysis of morphine glucuronides in human plasma by negative ion chemical ionization mass spectrometry.
2002 Apr
Pharmacokinetic modeling to predict morphine and morphine-6-glucuronide plasma concentrations in healthy young volunteers.
2002 Aug
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
A polymorphism (A118G) in the mu-opioid receptor gene affects the response to morphine-6-glucuronide in humans.
2002 Jan
Contribution of morphine-6-glucuronide to antinociception following intravenous administration of morphine to healthy volunteers.
2002 May
Increased CNS uptake and enhanced antinociception of morphine-6-glucuronide in rats after inhibition of P-glycoprotein.
2002 Oct
Rapid and simple method to determine morphine and its metabolites in rat plasma by liquid chromatography-mass spectrometry.
2003 Apr 25
Comparison of morphine-6-glucuronide and morphine on respiratory depressant and antinociceptive responses in wild type and mu-opioid receptor deficient mice.
2003 Dec
Relationships among morphine metabolism, pain and side effects during long-term treatment: an update.
2003 Jan
Analgesic effects of morphine and morphine-6-glucuronide in a transcutaneous electrical pain model in healthy volunteers.
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
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
Structure-activity relationships of some opiate glycosides.
2003 Mar 24
Gateways to clinical trials.
2003 May
Encapsulation of an intrathecal catheter.
2003 May
Opioid plasma concentration during switching from morphine to methadone: preliminary data.
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
Opiate recidivism in a drug-treatment program: comparison of hair and urine data.
2003 Oct
Pharmacokinetics of high doses of intramuscular and oral heroin in narcotic addicts.
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
Evidence for an active transport of morphine-6-beta-d-glucuronide but not P-glycoprotein-mediated at the blood-brain barrier.
2003 Sep
Isoform selectivity and kinetics of morphine 3- and 6-glucuronidation by human udp-glucuronosyltransferases: evidence for atypical glucuronidation kinetics by UGT2B7.
2003 Sep
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
  • Download
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
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
SOLVATE->ANHYDROUS
METABOLIC ENZYME -> SUBSTRATE
TARGET -> AGONIST
Related Record Type Details
PARENT -> METABOLITE ACTIVE
MAJOR
Related Record Type Details
ACTIVE MOIETY