Methylscopolamine bromide

Identification

Name
Methylscopolamine bromide
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
Synonyms
  • (−)-scopolamine methobromide
  • (−)-scopolamine methyl bromide
  • Hyoscine Methobromide
  • Hyoscine methyl bromide
  • Methscopolamine bromide
  • N-methylhyoscine bromide
  • N-methylscopolammonium bromide
  • Scopolamine Methobromide
  • Scopolamine methyl bromide
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Methscopolamine BromideTablet2.5 mg/1OralE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2011-03-16Not applicableUs
Methscopolamine BromideTablet2.5 mg/1OralA. Aarons2009-10-222015-12-29Us
Methscopolamine BromideTablet5 mg/1OralE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2011-07-27Not applicableUs
Methscopolamine BromideTablet5 mg/1OralA. Aarons2009-10-222015-12-29Us
PamineTablet2.5 mg/1OralPharma Derm, A Division Of Fougera Pharmaceuticals Inc.1953-04-092015-12-29Us
PamineTablet2.5 mg/1OralPharma Derm, A Division Of Fougera Pharmaceuticals Inc.1953-04-09Not applicableUs
Pamine ForteTablet5 mg/1OralPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2003-03-25Not applicableUs
Pamine ForteTablet5 mg/1OralPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2003-03-252015-12-29Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MethscopolamineTablet5 mg/1OralGolden State Medical Supply2006-12-28Not applicableUs64376 0604 61 nlmimage10 f608fb57
Methscopolamine BromideTablet5 mg/1OralPd Rx Pharmaceuticals, Inc.2013-10-01Not applicableUs
Methscopolamine BromideTablet2.5 mg/1OralBreckenridge Pharmaceutical, Inc.2012-05-21Not applicableUs
Methscopolamine BromideTablet2.5 mg/1OralBoca Pharmacal, Inc.2006-12-28Not applicableUs
Methscopolamine BromideTablet5 mg/1OralBayshore Pharmaceuticals, LLC2013-10-01Not applicableUs
Methscopolamine BromideTablet5 mg/1OralBreckenridge Pharmaceutical, Inc.2012-05-21Not applicableUs
Methscopolamine BromideTablet5 mg/1OralBoca Pharmacal, Inc.2006-12-28Not applicableUs
Methscopolamine BromideTablet2.5 mg/1OralPd Rx Pharmaceuticals, Inc.2013-10-01Not applicableUs
Methscopolamine BromideTablet2.5 mg/1OralBayshore Pharmaceuticals, LLC2013-10-01Not applicableUs
International/Other Brands
Pamine
Categories
UNII
RTN51LK7WL
CAS number
155-41-9
Weight
Average: 398.291
Monoisotopic: 397.088870908
Chemical Formula
C18H24BrNO4
InChI Key
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
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][[email protected]]12C[[email protected]@H](C[[email protected]@]([H])(C3OC13)[N+]2(C)C)OC(=O)[[email protected]](CO)C1=CC=CC=C1

Pharmacology

Indication

Used as adjunctive therapy for the treatment of peptic ulcer. Also used to treat nausea and vomiting due to motion sickness.

Structured Indications
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.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Human
AMuscarinic acetylcholine receptor M2
antagonist
Human
UMuscarinic acetylcholine receptor M3
antagonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB14605
KEGG Drug
D00715
PubChem Compound
23724781
PubChem Substance
46506260
ChemSpider
26329507
ChEBI
6845
Therapeutic Targets Database
DAP001126
PharmGKB
PA164784032
Wikipedia
Methylscopolamine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Nycomed us inc
  • Novartis consumer health inc
Packagers
Dosage forms
FormRouteStrength
TabletOral2.5 mg/1
TabletOral5 mg/1
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)225 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.8889
CYP450 2D6 inhibitorNon-inhibitor0.9036
CYP450 2C19 inhibitorNon-inhibitor0.8401
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Hydroxy acids and derivatives
Sub Class
Beta hydroxy acids and derivatives
Direct Parent
Beta hydroxy acids and derivatives
Alternative Parents
Benzene and substituted derivatives / Piperidines / Morpholines / N-alkylpyrrolidines / Tetraalkylammonium salts / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Epoxides / Dialkyl ethers
show 9 more
Substituents
Beta-hydroxy acid / Monocyclic benzene moiety / Oxazinane / Piperidine / Morpholine / N-alkylpyrrolidine / Benzenoid / Tetraalkylammonium salt / Pyrrolidine / Quaternary ammonium salt
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c 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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
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:17139284]
  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:17016423]
  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. doi: 10.1111/j.1476-5381.2010.00810.x. [PubMed:20590642]
Kind
Protein
Organism
Human
Pharmacological action
Yes
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...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
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. doi: 10.1007/s12640-009-9071-8. Epub 2009 Jun 30. [PubMed:19565307]
  2. 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
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...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
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. doi: 10.1124/mol.108.054452. Epub 2009 Jun 4. [PubMed:19498041]
  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:12815157]
  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. doi: 10.1002/pros.21188. [PubMed:20687226]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:37