Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H27NO9.2H2O |
| Molecular Weight | 497.4923 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])C=C[C@@H]2O[C@@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)C(O)=O)=CC=C3O
InChI
InChIKey=NRBQUVXMCUQJPZ-WFLHAITMSA-N
InChI=1S/C23H27NO9.2H2O/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);2*1H2/t10-,11+,13-,15-,16-,17+,19-,20-,22+,23-;;/m0../s1
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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
| Title | Date | PubMed |
|---|---|---|
| Opioid effect on breathing frequency and thermogenesis in mice lacking exon 2 of the mu-opioid receptor gene. | 2001 |
|
| Morphine-6beta-glucuronide modulates the expression of inducible nitric oxide synthase. | 2001 Aug |
|
| Simultaneous determination of morphine and its glucuronides in rat hair and rat plasma by reversed-phase liquid chromatography with electrospray ionization mass spectrometry. | 2001 Aug |
|
| 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 |
|
| Blood-brain barrier transport and brain distribution of morphine-6-glucuronide in relation to the antinociceptive effect in rats--pharmacokinetic/pharmacodynamic modelling. | 2001 Dec |
|
| Hydrophobic forms of morphine-6-glucosides. | 2001 Jun 4 |
|
| Mu opioid receptor efficacy and potency of morphine-6-glucuronide in neonatal guinea pig brainstem membranes: comparison with transfected CHO cells. | 2001 Mar 15 |
|
| Morphine-6 beta-glucuronide induces potent immunomodulation. | 2001 May |
|
| Limited phase I study of morphine-3-glucuronide. | 2001 Nov |
|
| Limited sampling approach. | 2001 Nov |
|
| Discriminative stimulus effects of intravenous heroin and its metabolites in rhesus monkeys: opioid and dopaminergic mechanisms. | 2001 Nov |
|
| Morphine-6beta-glucuronide and morphine-3-glucuronide, opioid receptor agonists with different potencies. | 2001 Nov 1 |
|
| Arterial and venous pharmacokinetics of intravenous heroin in subjects who are addicted to narcotics. | 2001 Sep |
|
| [Issues in cancer pain management]. | 2001 Sep |
|
| Wheel running attenuates the antinociceptive properties of morphine and its metabolite, morphine-6-glucuronide, in rats. | 2001 Sep 1-15 |
|
| Ultrafast liquid chromatography/tandem mass spectrometry bioanalysis of polar analytes using packed silica columns. | 2002 |
|
| The bioavailability and pharmacokinetics of subcutaneous, nebulized and oral morphine-6-glucuronide. | 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 modeling to predict morphine and morphine-6-glucuronide plasma concentrations in healthy young volunteers. | 2002 Aug |
|
| Pharmacokinetic modelling of morphine, morphine-3-glucuronide and morphine-6-glucuronide in plasma and cerebrospinal fluid of neurosurgical patients after short-term infusion of morphine. | 2002 Dec |
|
| 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 |
|
| 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 |
|
| Colostrum morphine concentrations during postcesarean intravenous patient-controlled analgesia. | 2002 Jan |
|
| 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 |
|
| 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 |
|
| Association between the cortisol response to opioid blockade and the Asn40Asp polymorphism at the mu-opioid receptor locus (OPRM1). | 2003 Apr 1 |
|
| Rapid and simple method to determine morphine and its metabolites in rat plasma by liquid chromatography-mass spectrometry. | 2003 Apr 25 |
|
| 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 |
|
| Structure-activity relationships of some opiate glycosides. | 2003 Mar 24 |
|
| Encapsulation of an intrathecal catheter. | 2003 May |
|
| Postoperative pain in the neonate: age-related differences in morphine requirements and metabolism. | 2003 Nov |
|
| High levels of morphine-6-glucuronide in street heroin addicts. | 2003 Nov |
|
| 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 |
|
| Development and validation of a liquid chromatography-mass spectrometry assay for the determination of opiates and cocaine in meconium. | 2003 Sep 5 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:36:46 GMT 2023
by
admin
on
Fri Dec 15 15:36:46 GMT 2023
|
| Record UNII |
ARKJBVK150
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
ARKJBVK150
Created by
admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
|
PRIMARY | |||
|
71308353
Created by
admin on Fri Dec 15 15:36:46 GMT 2023 , Edited by admin on Fri Dec 15 15:36:46 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |
|
||
|
PARENT -> DERIVATIVE |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
|
||
|
ANHYDROUS->SOLVATE |
|
