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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:32:52 UTC
HMDB IDHMDB15429
Secondary Accession NumbersNone
Metabolite Identification
Common NameMetocurine
DescriptionMetocurine is only found in individuals that have used or taken this drug. It is a non-depolarizing muscle relaxant. Patients on chronic anticonvulsant drugs are relatively resistant to metocurine.(PMID: 9915319 )Metocurine antagonizes the neurotransmitter action of acetylcholine by binding competitively with cholinergic receptor sites on the motor end-plate. This antagonism is inhibited, and neuromuscular block reversed, by acetylcholinesterase inhibitors such as neostigmine, edrophonium, and pyridostigmine.
Structure
Thumb
Synonyms
ValueSource
DimethyltubocurarineChEMBL
Chemical FormulaC40H48N2O6
Average Molecular Weight652.8189
Monoisotopic Molecular Weight652.351237278
IUPAC Name(1S,16R)-9,10,21,25-tetramethoxy-15,15,30,30-tetramethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24,26,31,35-dodecaene-15,30-diium
Traditional Namemetocurine
CAS Registry Number5152-30-7
SMILES
[H][C@@]12CC3=CC=C(OC4=C5C(CC[N+](C)(C)[C@]5([H])CC5=CC(OC6=C(OC)C=C(CC[N+]1(C)C)C2=C6)=C(OC)C=C5)=CC(OC)=C4OC)C=C3
InChI Identifier
InChI=1S/C40H48N2O6/c1-41(2)17-15-27-22-34(44-6)36-24-30(27)31(41)19-25-9-12-29(13-10-25)47-40-38-28(23-37(45-7)39(40)46-8)16-18-42(3,4)32(38)20-26-11-14-33(43-5)35(21-26)48-36/h9-14,21-24,31-32H,15-20H2,1-8H3/q+2/t31-,32+/m0/s1
InChI KeyInChIKey=JFXBEKISTKFVAB-AJQTZOPKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassBenzylisoquinolines
Direct ParentBenzylisoquinolines
Alternative Parents
Substituents
  • Benzylisoquinoline
  • Diaryl ether
  • Tetrahydroisoquinoline
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Quaternary ammonium salt
  • Oxacycle
  • Azacycle
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Neuromuscular Nondepolarizing Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.42e-06 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.42e-06 mg/mLALOGPS
logP2.36ALOGPS
logP-1.8ChemAxon
logS-8.1ALOGPS
pKa (Strongest Acidic)12.99ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.38 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity211.94 m3·mol-1ChemAxon
Polarizability73.46 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01336
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01336
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01336
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID19961
KEGG Compound IDC07919
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimethyltubocurarinium
NuGOwiki LinkHMDB15429
Metagene LinkHMDB15429
METLIN IDNot Available
PubChem Compound21233
PDB IDCU9
ChEBI ID339465
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Spacek A, Neiger FX, Krenn CG, Hoerauf K, Kress HG: Rocuronium-induced neuromuscular block is affected by chronic carbamazepine therapy. Anesthesiology. 1999 Jan;90(1):109-12. [9915319 ]
  2. Spacek A, Neiger FX, Krenn CG, Hoerauf K, Kress HG: Rocuronium-induced neuromuscular block is affected by chronic carbamazepine therapy. Anesthesiology. 1999 Jan;90(1):109-12. [9915319 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
References
  1. Son SL, Waud DR: Effects of non-depolarizing neuromuscular blocking agents on the cardiac vagus nerve in the guineapig. Br J Anaesth. 1980 Oct;52(10):981-7. [7437219 ]
General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular weight:
59764.8
References
  1. Liu M, Dilger JP: Synergy between pairs of competitive antagonists at adult human muscle acetylcholine receptors. Anesth Analg. 2008 Aug;107(2):525-33. [18633030 ]
  2. Liu M, Dilger JP: Site selectivity of competitive antagonists for the mouse adult muscle nicotinic acetylcholine receptor. Mol Pharmacol. 2009 Jan;75(1):166-73. Epub 2008 Oct 8. [18842832 ]
  3. Groebe DR, Dumm JM, Abramson SN: Irreversible inhibition of nicotinic acetylcholine receptors by the bipinnatins. Toxin activation and kinetics of receptor inhibition. J Biol Chem. 1994 Mar 25;269(12):8885-91. [8132625 ]
  4. Wang HL, Gao F, Bren N, Sine SM: Curariform antagonists bind in different orientations to the nicotinic receptor ligand binding domain. J Biol Chem. 2003 Aug 22;278(34):32284-91. Epub 2003 Jun 10. [12799358 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]