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Identification
Name Methylscopolamine
Accession Number DB00462 (APRD00314)
Type small molecule
Groups approved
Description

A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Epoxymethamine Bromide
  • Epoxytropine Tropate Methylbromide
  • Hyoscine Methobromide
  • Hyoscine Methylbromide
  • Lescopine Bromide
  • Methoscopylamine Bromide
  • Methscopolamine
  • Methscopolamine Methylbromide
  • Methylscopolamine Bromide
  • Methylscopolamine Hydrobromide
  • N-Methylhyoscine Bromide
  • N-Methylscopolamine Methylsulfate
  • N-Methylscopolammonium Bromide
  • Scopolamin Methylbromide
  • Scopolamine Methobromide
  • Scopolamine Methylbromide
Brand names
  • Ampyrox
  • Blocan
  • Daipin
  • Diopal
  • Holopon
  • Mescopil
  • Neo-Avagal
  • Nutrop
  • Pamine
  • Paraspan
  • Proscomide
  • Restropin
  • Transderm Scop
Brand name mixtures
  • Biosol-M-Aquadrops liq (methscopolamine bromide + neomycin sulfate)
  • Neomix-pamine Scour Bolus (methscopolamine bromide + neomycin sulfate)
  • Neomix-pamine Solution (methscopolamine bromide + neomycin sulfate)
  • Neosol M Aquadrops (methscopolamine bromide + neomycin)
  • Scour solution (methscopolamine bromide + neomycin)
  • Scour solution coop (methscopolamine bromide + neomycin)
Categories
  • Antispasmodics
  • Anticholinergic Agents
  • Parasympatholytics
CAS number 155-41-9
Weight Average: 398.291
Monoisotopic: 397.088870908
Chemical Formula C18H24BrNO4
InChI Key InChIKey=CXYRUNPLKGGUJF-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
Plain Text
IUPAC Name
(1S,5S)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenylacetates
  • Tropanes
  • Alkaloids and Alkaloid Derivatives
Substructures
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Acetates
  • Phenylacetates
  • Pyrrolidines
  • Ethers
  • Benzene and Derivatives
  • Quaternary Ammonium Salts
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Aromatic compounds
  • Tropanes
  • Morpholines
  • Alkaloids and Alkaloid Derivatives
  • Epoxides
  • Piperidines
  • Cations
Pharmacology
Indication Used as adjunctive therapy for the treatment of peptic ulcer. Also used to treat nausea and vomiting due to motion sickness.
Pharmacodynamics Methscopolamine 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 action Methscopolamine 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.
Absorption Poorly and unreliably absorbed, total absorption is 10-25%.
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Little is known about the fate and excretion of methscopolamine.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Symptoms 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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Nycomed us inc
  • Novartis consumer health inc
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Pamine Forte 60 5 mg tablet Box 234.68 USD box
Transderm-Scop 1.5 mg (1 Box Contains 4 Patches) 14.87 USD patch
Transderm-Scop 1.5 mg (1 Box Contains 10 Patches) 12.04 USD patch
Transderm-scop 1.5 mg/72hr 12.01 USD each
Pamine fq dose pack kit 2.77 USD each
Pamine 2.5 mg tablet 2.72 USD tablet
Methscopolamine brom 5 mg tablet 2.09 USD tablet
Patents Not Available
Properties
State solid
Melting point 225 oC
Experimental Properties
Property Value Source
water solubility Freely soluble PhysProp
logP -2.58 PhysProp
Caco2 permeability -6.16 [ADME Research, USCD] BiGG
Predicted Properties
Property Value Source
water solubility 1.32e-02 g/l ALOGPS
logP -1.96 ALOGPS
logP -3.27 ChemAxon Molconvert
logS -4.48 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 55.76 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 95.63 ChemAxon Molconvert
polarizability 48.12 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00715 Link_out
PubChem Compound 23724781 Link_out
PubChem Substance 46506260 Link_out
ChemSpider 3977 Link_out
Therapeutic Targets Database DAP001126 Link_out
PharmGKB PA450435 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Methylscopolamine Link_out
ATC Codes
  • A03BB03
  • S01FA03
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: antagonist

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 Pi turnover

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P08172 Link_out
Gene: CHRM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: antagonist

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 Pi turnover

Organism class: human
UniProt ID: P20309 Link_out
Gene: CHRM3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:39

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.