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Identification
NameMethylscopolamine bromide
Accession NumberDB00462  (APRD00314)
TypeSmall Molecule
GroupsApproved
Description

A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(−)-scopolamine methobromideNot AvailableNot Available
(−)-scopolamine methyl bromideNot AvailableNot Available
Hyoscine MethobromideNot AvailableINN
Hyoscine methyl bromideNot AvailableNot Available
Methscopolamine bromideNot AvailableNot Available
N-methylhyoscine bromideNot AvailableNot Available
N-methylscopolammonium bromideNot AvailableNot Available
PamineNot AvailableNot Available
Scopolamine MethobromideNot AvailableNot Available
Scopolamine methyl bromideNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Methscopolamine Bromidetablet2.5 mgoralE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2011-03-16Not AvailableUs
Methscopolamine Bromidetablet5 mgoralE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2011-07-27Not AvailableUs
Paminetablet2.5 mgoralPharma Derm A Division Of Fougera Pharmaceuticals Inc.1953-04-09Not AvailableUs
Pamine Fortetablet5 mgoralPharma Derm A Division Of Fougera Pharmaceuticals Inc.2003-03-25Not AvailableUs
Paminetablet2.5 mgoralPharma Derm A Division Of Fougera Pharmaceuticals Inc.1953-04-09Not AvailableUs
Pamine Fortetablet5 mgoralPharma Derm A Division Of Fougera Pharmaceuticals Inc.2003-03-25Not AvailableUs
Methscopolamine Bromidetablet2.5 mgoralA. Aarons2009-10-22Not AvailableUs
Methscopolamine Bromidetablet5 mgoralA. Aarons2009-10-22Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Methscopolamine Bromidetablet2.5 mgoralBreckenridge Pharmaceutical, Inc.2012-05-21Not AvailableUs
Methscopolamine Bromidetablet5 mgoralBreckenridge Pharmaceutical, Inc.2012-05-21Not AvailableUs
Methscopolaminetablet5 mgoralGolden State Medical Supply, Inc.2006-12-28Not AvailableUs
Methscopolamine Bromidetablet2.5 mgoralBoca Pharmacal, LLC2006-12-28Not AvailableUs
Methscopolamine Bromidetablet5 mgoralBoca Pharmacal, LLC2006-12-28Not AvailableUs
Methscopolamine Bromidetablet2.5 mgoralBAYSHORE PHARMACEUTICALS LLC2013-10-01Not AvailableUs
Methscopolamine Bromidetablet5 mgoralBAYSHORE PHARMACEUTICALS LLC2013-10-01Not AvailableUs
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixtures
Brand NameIngredients
AlleRxchlorpheniramine and methscopolamine
Extendryldexchlorpheniramine, methscopolamine, and phenylephrine
SaltsNot Available
Categories
CAS number155-41-9
WeightAverage: 398.291
Monoisotopic: 397.088870908
Chemical FormulaC18H24BrNO4
InChI KeyCXYRUNPLKGGUJF-JIRGPDKYSA-M
InChI
InChI=1S/C18H24NO4.BrH/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11;/h3-7,12-17,20H,8-10H2,1-2H3;1H/q+1;/p-1/t12?,13-,14+,15+,16?,17?;/m1./s1
IUPAC Name
(1S,5S)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-9-ium bromide
SMILES
[Br-].[H][C@]12C[C@@H](C[C@@]([H])(C3OC13)[N+]2(C)C)OC(=O)[C@H](CO)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Beta-hydroxy acid
  • N-alkylpyrrolidine
  • Piperidine
  • Oxazinane
  • Morpholine
  • Hydroxy acid
  • Quaternary ammonium salt
  • Pyrrolidine
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic bromide salt
  • Organic salt
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed as adjunctive therapy for the treatment of peptic ulcer. Also used to treat nausea and vomiting due to motion sickness.
PharmacodynamicsMethscopolamine is a muscarinic antagonist structurally similar to the neurotransmitter acetylcholine and acts by blocking the muscarinic acetylcholine receptors and is thus classified as an anticholinergic. Methscopolamine has many uses including the prevention of motion sickness. It is not clear how Methscopolamine prevents nausea and vomiting due to motion sickness. The vestibular part of the ear is very important for balance. When a person becomes disoriented due to motion, the vestibule sends a signal through nerves to the vomiting center in the brain, and vomiting occurs. Acetylcholine is a chemical that nerves use to transmit messages to each other. It is believe that Methscopolamine prevents communication between the nerves of the vestibule and the vomiting center in the brain by blocking the action of acetylcholine. Methscopolamine also may work directly on the vomiting center. Methscopolamine must be taken before the onset of motion sickness to be effective.
Mechanism of actionMethscopolamine acts by interfering with the transmission of nerve impulses by acetylcholine in the parasympathetic nervous system (specifically the vomiting center). It does so by acting as a muscarinic antagonist.
AbsorptionPoorly and unreliably absorbed, total absorption is 10-25%.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Little is known about the fate and excretion of methscopolamine.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of a methscopolamine overdose include headache, nausea, vomiting, dry mouth, difficulty swallowing, blurred vision, dilated pupils, hot, dry skin, dizziness; drowsiness, confusion, anxiety, seizures, weak pulse, and an irregular heartbeat. In addition, a curare-like action may occur, i.e., neuromuscular blockade leading to muscular weakness and possible paralysis.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8093
Blood Brain Barrier+0.6997
Caco-2 permeable+0.6465
P-glycoprotein substrateSubstrate0.5869
P-glycoprotein inhibitor INon-inhibitor0.9276
P-glycoprotein inhibitor IINon-inhibitor0.8179
Renal organic cation transporterNon-inhibitor0.5677
CYP450 2C9 substrateNon-substrate0.7319
CYP450 2D6 substrateNon-substrate0.7662
CYP450 3A4 substrateSubstrate0.6154
CYP450 1A2 substrateNon-inhibitor0.8458
CYP450 2C9 substrateNon-inhibitor0.8889
CYP450 2D6 substrateNon-inhibitor0.9036
CYP450 2C19 substrateNon-inhibitor0.8401
CYP450 3A4 substrateNon-inhibitor0.8293
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.921
Ames testNon AMES toxic0.7609
CarcinogenicityNon-carcinogens0.9189
BiodegradationNot ready biodegradable0.8731
Rat acute toxicity2.5731 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9778
hERG inhibition (predictor II)Non-inhibitor0.871
Pharmacoeconomics
Manufacturers
  • Nycomed us inc
  • Novartis consumer health inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral2.5 mg
Tabletoral5 mg
Prices
Unit descriptionCostUnit
Pamine Forte 60 5 mg tablet Box234.68USD box
Transderm-Scop 1.5 mg (1 Box Contains 4 Patches)14.87USD patch
Transderm-Scop 1.5 mg (1 Box Contains 10 Patches)12.04USD patch
Transderm-scop 1.5 mg/72hr12.01USD each
Pamine fq dose pack kit2.77USD each
Pamine 2.5 mg tablet2.72USD tablet
Methscopolamine brom 5 mg tablet2.09USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point225 °CNot Available
water solubilityFreely solubleNot Available
logP-2.58Not Available
Caco2 permeability-6.16ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0132 mg/mLALOGPS
logP-2ALOGPS
logP-3.3ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity95.63 m3·mol-1ChemAxon
Polarizability48.12 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
CinitaprideAnticholinergic agents like methylscopolamine may reduce the action of cinitapride.
DonepezilPossible antagonism of action
GalantaminePossible antagonism of action
TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Methylscopolamine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
TrimethobenzamideTrimethobenzamide and Methylscopolamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TriprolidineTriprolidine and Methylscopolamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TrospiumTrospium and Methylscopolamine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food InteractionsNot Available

Targets

1. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Figueroa KW, Suga H, Ehlert FJ: Investigating the interaction of McN-A-343 with the M muscarinic receptor using its nitrogen mustard derivative and ACh mustard. Br J Pharmacol. 2010 Jul;160(6):1534-49. Pubmed

2. Muscarinic acetylcholine receptor M2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

References:

  1. Soukup O, Proska J, Binder J, Karasova JZ, Tobin G, Jun D, Marek J, Musilek K, Fusek J, Kuca K: Methylacridinium and its cholinergic properties. Neurotox Res. 2009 Nov;16(4):372-7. Epub 2009 Jun 30. Pubmed
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. Muscarinic acetylcholine receptor M3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M3 P20309 Details

References:

  1. Sykes DA, Dowling MR, Charlton SJ: Exploring the mechanism of agonist efficacy: a relationship between efficacy and agonist dissociation rate at the muscarinic M3 receptor. Mol Pharmacol. 2009 Sep;76(3):543-51. Epub 2009 Jun 4. Pubmed
  2. Voigtlander U, Johren K, Mohr M, Raasch A, Trankle C, Buller S, Ellis J, Holtje HD, Mohr K: Allosteric site on muscarinic acetylcholine receptors: identification of two amino acids in the muscarinic M2 receptor that account entirely for the M2/M5 subtype selectivities of some structurally diverse allosteric ligands in N-methylscopolamine-occupied receptors. Mol Pharmacol. 2003 Jul;64(1):21-31. Pubmed
  3. Saito M, Kazuyama E, Shimizu S, Dimitriadis F, Kinoshita Y, Masuda E, Yamada S, Satoh K: Muscarinic receptors and their mRNAs in type 2 Goto-Kakizaki diabetic rat prostate. Prostate. 2010 Oct 1;70(14):1533-9. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10