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Identification
NameMetocurine
Accession NumberDB01336
Typesmall molecule
Groupsapproved
Description

Dimethyltubocurarinium (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
SynonymLanguageCode
DimethyltubocurarineNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
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[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8,10,12(34),18(33),19,21,24(32),25,27(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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassIsoquinolines and Derivatives
SubclassBenzylisoquinolines
Direct parentBenzylisoquinolines
Alternative parentsDiarylethers; Anisoles; Alkyl Aryl Ethers; Polyamines
Substituentsdiaryl ether; phenol ether; anisole; alkyl aryl ether; benzene; polyamine; ether; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
Pharmacology
IndicationMetocurine is a muscle relaxant.
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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.871
Blood Brain Barrier + 0.9597
Caco-2 permeable + 0.7462
P-glycoprotein substrate Substrate 0.8469
P-glycoprotein inhibitor I Non-inhibitor 0.6124
P-glycoprotein inhibitor II Non-inhibitor 0.82
Renal organic cation transporter Non-inhibitor 0.533
CYP450 2C9 substrate Non-substrate 0.8465
CYP450 2D6 substrate Non-substrate 0.5836
CYP450 3A4 substrate Substrate 0.6987
CYP450 1A2 substrate Non-inhibitor 0.9391
CYP450 2C9 substrate Non-inhibitor 0.9626
CYP450 2D6 substrate Non-inhibitor 0.908
CYP450 2C19 substrate Non-inhibitor 0.9468
CYP450 3A4 substrate Non-inhibitor 0.8976
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.976
Ames test AMES toxic 0.6059
Carcinogenicity Non-carcinogens 0.9074
Biodegradation Not ready biodegradable 0.8898
Rat acute toxicity 2.7086 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8306
hERG inhibition (predictor II) Non-inhibitor 0.6067
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility6.42e-06 g/lALOGPS
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 area55.38ChemAxon
rotatable bond count4ChemAxon
refractivity211.94ChemAxon
polarizability73.46ChemAxon
number of rings7ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  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
External Links
ResourceLink
KEGG CompoundC07919
PubChem Compound21233
PubChem Substance46508044
ChemSpider19961
BindingDB50094708
Therapeutic Targets DatabaseDAP000352
WikipediaDimethyltubocurarinium
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AmikacinThe agent increases the effect of muscle relaxant
AminophyllineTheophylline decreases the effect of muscle relaxant
AzathioprineThe agent decreases the effect of the muscle relaxant
CarbamazepineDecreases the effect of muscle relaxant
ClindamycinThe agent increases the effect of muscle relaxant
FosphenytoinPhenytoin decreases the effect of muscle relaxant
GentamicinThe agent increases the effect of muscle relaxant
LincomycinThe agent increases the effect of muscle relaxant
MercaptopurineThe agent dereases the effect of the muscle relaxant
NetilmicinThe agent increases the effect of muscle relaxant
OxtriphyllineTheophylline decreases the effect of muscle relaxant
PhenytoinPhenytoin decreases the effect of the muscle relaxant
PiperacillinThe agent increases the effect of the muscle relaxant
QuinidineThe quinine derivative increases the effect of the muscle relaxant
QuinineThe quinine derivative increases the effect of the muscle relaxant
TheophyllineTheophylline decreases the effect of the muscle relaxant
TobramycinThe agent increases the effect of the muscle relaxant
Food InteractionsNot Available

Targets

1. Neuronal acetylcholine receptor subunit alpha-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-2 Q15822 Details

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. Pubmed
  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. Pubmed
  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
  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
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Muscarinic acetylcholine receptor M2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

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

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Drug created on June 30, 2007 12:07 / Updated on September 16, 2013 17:14