Morphine glucuronide

Identification

Name
Morphine glucuronide
Accession Number
DB06409
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • M6G
  • Morphine 6-beta-D-glucopyranosiduronide
  • Morphine 6-glucuronide
  • Morphine glucuronide
  • Morphine-6-glucuronide
External IDs
CEE 04-410 / CEE-04-410
Categories
UNII
64Y9KYM60R
CAS number
20290-10-2
Weight
Average: 461.4618
Monoisotopic: 461.168581467
Chemical Formula
C23H27NO9
InChI Key
GNJCUHZOSOYIEC-GAROZEBRSA-N
InChI
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
IUPAC Name
(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-yl]oxy}oxane-2-carboxylic acid
SMILES
[H][C@]12C=C[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4O

Pharmacology

Indication

Investigated for use/treatment in pain (acute or chronic).

Pharmacodynamics
Not Available
Mechanism of action

M6G, morphine-6-glucuronide, is an active metabolite from liver metabolism of morphine. M6G has a similar mechanism of action to morphine, primarily acting on the mu opioid receptor, with slightly higher affinity to the delta receptor than and lower affinity for the kappa receptor than morphine. It is proposed that M6G has a lower affinity than morphine at the mu2 receptor but equal affinity to the u1 receptor, but these results are uncertain and are undergoing further investigation. The precise mechanism of the analgesic action of morphine is unknown. However, specific CNS opiate receptors have been identified and likely play a role in the expression of analgesic effects. The mechanism of respiratory depression involves a reduction in the responsiveness of the brain stem respiratory centers to increases in carbon dioxide tension and to electrical stimulation.

TargetActionsOrganism
UMu-type opioid receptorNot AvailableHumans
UDelta-type opioid receptorNot AvailableHumans
UKappa-type opioid receptorNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
  1. Dahan A, van Dorp E, Smith T, Yassen A: Morphine-6-glucuronide (M6G) for postoperative pain relief. Eur J Pain. 2008 May;12(4):403-11. Epub 2007 Sep 14. [PubMed:17869146]
External Links
Human Metabolome Database
HMDB0041937
KEGG Compound
C16578
ChemSpider
4514548
BindingDB
50370478
ChEBI
80581
ChEMBL
CHEMBL1330
ZINC
ZINC000014089740
Wikipedia
Morphine-6-glucuronide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentPostoperative pain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility9.19 mg/mLALOGPS
logP0.13ALOGPS
logP-3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.87ChemAxon
pKa (Strongest Basic)9.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149.15 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity112.4 m3·mol-1ChemAxon
Polarizability45.1 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da

Drug created on March 19, 2008 10:30 / Updated on March 01, 2020 19:39

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