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Identification
NameMetocurine
Accession NumberDB01336
TypeSmall Molecule
GroupsApproved
DescriptionDimethyltubocurarinium (INN) or metocurine (USAN), also known as dimethyltubocurarine, is a non-depolarizing muscle relaxant. Patients on chronic anticonvulsant drugs are relatively resistant to metocurine.(PMID: 9915319)
Structure
Thumb
Synonyms
Dimethyltubocurarine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIV0M92G2U26
CAS number5152-30-7
WeightAverage: 652.8189
Monoisotopic: 652.351237278
Chemical FormulaC40H48N2O6
InChI KeyJFXBEKISTKFVAB-AJQTZOPKSA-N
InChI
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
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
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
Pharmacology
IndicationMetocurine is a muscle relaxant.
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionMetocurine 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Neuronal acetylcholine receptor subunit alpha-2Proteinyes
antagonist
HumanQ15822 details
Muscarinic acetylcholine receptor M2Proteinunknown
antagonist
HumanP08172 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinMetocurine may increase the arrhythmogenic activities of Acetyldigitoxin.Approved
AclarubicinAclarubicin may increase the respiratory depressant activities of Metocurine.Investigational
AmikacinAmikacin may increase the respiratory depressant activities of Metocurine.Approved, Vet Approved
AmrubicinAmrubicin may increase the respiratory depressant activities of Metocurine.Approved, Investigational
annamycinannamycin may increase the respiratory depressant activities of Metocurine.Investigational
AnvirzelMetocurine may increase the arrhythmogenic activities of Anvirzel.Investigational
ApramycinApramycin may increase the respiratory depressant activities of Metocurine.Experimental, Vet Approved
ArbekacinArbekacin may increase the respiratory depressant activities of Metocurine.Approved
Botulinum Toxin Type ABotulinum Toxin Type A may increase the neuromuscular blocking activities of Metocurine.Approved, Investigational
Botulinum Toxin Type BMetocurine may increase the neuromuscular blocking activities of Botulinum Toxin Type B.Approved
BumetanideBumetanide may decrease the neuromuscular blocking activities of Metocurine.Approved
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Metocurine.Approved
ChlortetracyclineChlortetracycline may increase the neuromuscular blocking activities of Metocurine.Approved, Vet Approved
ClindamycinClindamycin may increase the neuromuscular blocking activities of Metocurine.Approved, Vet Approved
ColistimethateColistimethate may increase the neuromuscular blocking activities of Metocurine.Approved, Vet Approved
CyclosporineCyclosporine may increase the neuromuscular blocking activities of Metocurine.Approved, Investigational, Vet Approved
DaunorubicinDaunorubicin may increase the respiratory depressant activities of Metocurine.Approved
DemeclocyclineDemeclocycline may increase the neuromuscular blocking activities of Metocurine.Approved
DeslanosideMetocurine may increase the arrhythmogenic activities of Deslanoside.Approved
DigitoxinMetocurine may increase the arrhythmogenic activities of Digitoxin.Approved
DigoxinMetocurine may increase the arrhythmogenic activities of Digoxin.Approved
DihydrostreptomycinDihydrostreptomycin may increase the respiratory depressant activities of Metocurine.Vet Approved
DoxorubicinDoxorubicin may increase the respiratory depressant activities of Metocurine.Approved, Investigational
DoxycyclineDoxycycline may increase the neuromuscular blocking activities of Metocurine.Approved, Investigational, Vet Approved
EpirubicinEpirubicin may increase the respiratory depressant activities of Metocurine.Approved
Etacrynic acidEtacrynic acid may decrease the neuromuscular blocking activities of Metocurine.Approved
FramycetinFramycetin may increase the respiratory depressant activities of Metocurine.Approved
FurosemideFurosemide may decrease the neuromuscular blocking activities of Metocurine.Approved, Vet Approved
GeneticinGeneticin may increase the respiratory depressant activities of Metocurine.Experimental
GentamicinGentamicin may increase the respiratory depressant activities of Metocurine.Approved, Vet Approved
GENTAMICIN C1AGENTAMICIN C1A may increase the respiratory depressant activities of Metocurine.Experimental
Hygromycin BHygromycin B may increase the respiratory depressant activities of Metocurine.Vet Approved
IdarubicinIdarubicin may increase the respiratory depressant activities of Metocurine.Approved
INNO-206INNO-206 may increase the respiratory depressant activities of Metocurine.Investigational
KanamycinKanamycin may increase the respiratory depressant activities of Metocurine.Approved, Vet Approved
LithiumLithium may increase the neuromuscular blocking activities of Metocurine.Approved
Magnesium hydroxideMagnesium hydroxide may increase the neuromuscular blocking activities of Metocurine.Approved
Magnesium oxideMagnesium oxide may increase the neuromuscular blocking activities of Metocurine.Approved
Magnesium salicylateMagnesium salicylate may increase the neuromuscular blocking activities of Metocurine.Approved
Magnesium SulfateMagnesium Sulfate may increase the neuromuscular blocking activities of Metocurine.Approved, Vet Approved
MetrizamideMetrizamide may increase the respiratory depressant activities of Metocurine.Approved
MinocyclineMinocycline may increase the neuromuscular blocking activities of Metocurine.Approved, Investigational
NeamineNeamine may increase the respiratory depressant activities of Metocurine.Experimental
NeomycinNeomycin may increase the respiratory depressant activities of Metocurine.Approved, Vet Approved
NetilmicinNetilmicin may increase the respiratory depressant activities of Metocurine.Approved
OuabainMetocurine may increase the arrhythmogenic activities of Ouabain.Approved
OxytetracyclineOxytetracycline may increase the neuromuscular blocking activities of Metocurine.Approved, Vet Approved
ParomomycinParomomycin may increase the respiratory depressant activities of Metocurine.Approved, Investigational
PirarubicinPirarubicin may increase the respiratory depressant activities of Metocurine.Investigational
PiretanidePiretanide may decrease the neuromuscular blocking activities of Metocurine.Experimental
PlicamycinPlicamycin may increase the respiratory depressant activities of Metocurine.Approved, Withdrawn
Polymyxin B SulfatePolymyxin B Sulfate may increase the neuromuscular blocking activities of Metocurine.Approved, Vet Approved
ProcainamideProcainamide may increase the neuromuscular blocking activities of Metocurine.Approved
PuromycinPuromycin may increase the respiratory depressant activities of Metocurine.Experimental
QuinidineQuinidine may increase the neuromuscular blocking activities of Metocurine.Approved
QuinineQuinine may increase the neuromuscular blocking activities of Metocurine.Approved
RibostamycinRibostamycin may increase the respiratory depressant activities of Metocurine.Approved
SisomicinSisomicin may increase the respiratory depressant activities of Metocurine.Investigational
SP1049CSP1049C may increase the respiratory depressant activities of Metocurine.Investigational
SpectinomycinSpectinomycin may increase the respiratory depressant activities of Metocurine.Approved, Vet Approved
StreptomycinStreptomycin may increase the respiratory depressant activities of Metocurine.Approved, Vet Approved
StreptozocinStreptozocin may increase the respiratory depressant activities of Metocurine.Approved
TetracyclineTetracycline may increase the neuromuscular blocking activities of Metocurine.Approved, Vet Approved
TobramycinTobramycin may increase the respiratory depressant activities of Metocurine.Approved, Investigational
TorasemideTorasemide may decrease the neuromuscular blocking activities of Metocurine.Approved
ValrubicinValrubicin may increase the respiratory depressant activities of Metocurine.Approved
VancomycinVancomycin may increase the neuromuscular blocking activities of Metocurine.Approved
ZorubicinZorubicin may increase the respiratory depressant activities of Metocurine.Experimental
Food InteractionsNot Available
References
Synthesis ReferenceNot 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. [PubMed:9915319 ]
External Links
ATC CodesM03AA04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.871
Blood Brain Barrier+0.9597
Caco-2 permeable+0.7462
P-glycoprotein substrateSubstrate0.8469
P-glycoprotein inhibitor INon-inhibitor0.6124
P-glycoprotein inhibitor IINon-inhibitor0.82
Renal organic cation transporterNon-inhibitor0.533
CYP450 2C9 substrateNon-substrate0.8465
CYP450 2D6 substrateNon-substrate0.5836
CYP450 3A4 substrateSubstrate0.6987
CYP450 1A2 substrateNon-inhibitor0.9391
CYP450 2C9 inhibitorNon-inhibitor0.9626
CYP450 2D6 inhibitorNon-inhibitor0.908
CYP450 2C19 inhibitorNon-inhibitor0.9468
CYP450 3A4 inhibitorNon-inhibitor0.8976
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.976
Ames testAMES toxic0.6059
CarcinogenicityNon-carcinogens0.9074
BiodegradationNot ready biodegradable0.8898
Rat acute toxicity2.7086 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8306
hERG inhibition (predictor II)Non-inhibitor0.6067
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Mass Spec (NIST)Not Available
SpectraNot Available
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

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Drug binding
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:
59764.82 Da
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. doi: 10.1213/ane.0b013e31817b4469. [PubMed: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. doi: 10.1124/mol.108.051060. Epub 2008 Oct 8. [PubMed: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. [PubMed: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. [PubMed:12799358 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
G-protein coupled acetylcholine receptor activity
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. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
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. [PubMed:7437219 ]
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Drug created on June 30, 2007 12:07 / Updated on August 17, 2016 12:23