Identification
- Generic Name
- Morphine glucuronide
- DrugBank Accession Number
- DB06409
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Morphine glucuronide (DB06409)
- Weight
- Average: 461.4618
Monoisotopic: 461.168581467 - Chemical Formula
- C23H27NO9
- Synonyms
- M6G
- Morphine 6-beta-D-glucopyranosiduronide
- Morphine 6-glucuronide
- Morphine glucuronide
- Morphine-6-glucuronide
- External IDs
- CEE 04-410
- CEE-04-410
Pharmacology
- Indication
Investigated for use/treatment in pain (acute or chronic).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism UMu-type opioid receptor Not Available Humans UDelta-type opioid receptor Not Available Humans UKappa-type opioid receptor Not Available Humans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 64Y9KYM60R
- CAS number
- 20290-10-2
- 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
References
- General References
- 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. [Article]
- 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
Phase Status Purpose Conditions Count 3 Completed Treatment Postoperative pain 1
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
Property Value Source Water Solubility 9.19 mg/mL ALOGPS logP 0.13 ALOGPS logP -3 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 2.87 Chemaxon pKa (Strongest Basic) 9.12 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 149.15 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 112.4 m3·mol-1 Chemaxon Polarizability 45.1 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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 at March 19, 2008 16:30 / Updated at February 21, 2021 18:52