Identification
- Summary
Methscopolamine bromide is a muscarinic antagonist used to treat peptic ulcers, nausea, vomiting, and motion sickness.
- Brand Names
- Pamine
- Generic Name
- Methscopolamine bromide
- DrugBank Accession Number
- DB00462
- Background
A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Methscopolamine bromide (DB00462)
- Weight
- Average: 398.297
Monoisotopic: 397.088871 - Chemical Formula
- C18H24BrNO4
- Synonyms
- (−)-scopolamine methobromide
- (−)-scopolamine methyl bromide
- Hyoscine methobromide
- Hyoscine methyl bromide
- Methscopolamine bromide
- Methylscopolamine bromide
- N-methylhyoscine bromide
- N-methylscopolammonium bromide
- Scopolamine methobromide
- Scopolamine methyl bromide
Pharmacology
- Indication
Used as adjunctive therapy for the treatment of peptic ulcer. Also used to treat nausea and vomiting due to motion sickness.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Adjunct therapy in treatment of Peptic ulcer •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AMuscarinic acetylcholine receptor M2 antagonistHumans AMuscarinic acetylcholine receptor M1 antagonistHumans UMuscarinic acetylcholine receptor M3 antagonistHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAclidinium The risk or severity of adverse effects can be increased when Methscopolamine bromide is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Methscopolamine bromide is combined with Adenosine. Alfentanil The risk or severity of adverse effects can be increased when Methscopolamine bromide is combined with Alfentanil. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Methscopolamine bromide. Amantadine The risk or severity of adverse effects can be increased when Methscopolamine bromide is combined with Amantadine. - Food Interactions
- Take before a meal. Take methscopolamine bromide 30 minutes before meals and at bedtime for optimal therapeutic effect.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Active Moieties
Name Kind UNII CAS InChI Key Methscopolamine ionic VDR09VTQ8U 13265-10-6 LZCOQTDXKCNBEE-IKIFYQGPSA-N - Product Images
- International/Other Brands
- Pamine
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Methscopolamine Bromide Tablet 5 mg/1 Oral Fougera Pharmaceuticals Inc. 2009-10-22 2013-12-31 US 
Methscopolamine Bromide Tablet 2.5 mg/1 Oral Fougera Pharmaceuticals Inc. 2009-10-22 2013-12-31 US Pamine Tablet 2.5 mg/1 Oral Pharma Derm, A Division Of Fougera Pharmaceuticals Inc. 1953-04-09 Not applicable US Pamine Tablet 2.5 mg/1 Oral Pharma Derm, A Division Of Fougera Pharmaceuticals Inc. 1953-04-09 2013-12-31 US Pamine Forte Tablet 5 mg/1 Oral Pharma Derm, A Division Of Fougera Pharmaceuticals Inc. 2003-03-25 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Methscopolamine Tablet 5 mg/1 Oral Golden State Medical Supply, Inc. 2006-12-28 2017-01-02 US 
Methscopolamine Bromide Tablet 2.5 mg/1 Oral AACE PHARMACEUTICALS, INC. 2024-02-05 Not applicable US Methscopolamine Bromide Tablet 2.5 mg/1 Oral E. Fougera & CO., A division of Fougera Pharmaceuticals Inc. 2011-03-16 Not applicable US Methscopolamine Bromide Tablet 5 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 2013-10-01 Not applicable US Methscopolamine Bromide Tablet 5 mg/1 Oral Bayshore Pharmaceuticals LLC 2013-10-01 Not applicable US
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- RTN51LK7WL
- CAS number
- 155-41-9
- InChI Key
- CXYRUNPLKGGUJF-RAFJPFSSSA-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
- (1R,2R,4S,5S,7S)-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@@]12O[C@]1([H])[C@H]1C[C@H](C[C@@H]2[N+]1(C)C)OC(=O)[C@H](CO)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014605
- KEGG Drug
- D00715
- PubChem Compound
- 23724781
- PubChem Substance
- 46506260
- ChemSpider
- 10481908
- 56092
- ChEBI
- 61276
- ChEMBL
- CHEMBL1354199
- Therapeutic Targets Database
- DAP001126
- PharmGKB
- PA164784032
- Wikipedia
- Methylscopolamine_bromide
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Nycomed us inc
- Novartis consumer health inc
- Packagers
- A. Aarons Inc.
- Kenwood Labs
- Novartis AG
- Dosage Forms
Form Route Strength Tablet Oral 10.000 mg Tablet Oral 2.5 mg/1 Tablet Oral 5 mg/1 - Prices
Unit description Cost Unit Pamine Forte 60 5 mg tablet Box 234.68USD 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/72hr 12.01USD each Pamine fq dose pack kit 2.77USD each Pamine 2.5 mg tablet 2.72USD tablet Methscopolamine brom 5 mg tablet 2.09USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 225 °C Not Available water solubility Freely soluble Not Available logP -2.58 Not Available Caco2 permeability -6.16 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.0132 mg/mL ALOGPS logP -2 ALOGPS logP -3.3 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 15.15 Chemaxon pKa (Strongest Basic) -2.7 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 59.06 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 95.63 m3·mol-1 Chemaxon Polarizability 33.35 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8093 Blood Brain Barrier + 0.6997 Caco-2 permeable + 0.6465 P-glycoprotein substrate Substrate 0.5869 P-glycoprotein inhibitor I Non-inhibitor 0.9276 P-glycoprotein inhibitor II Non-inhibitor 0.8179 Renal organic cation transporter Non-inhibitor 0.5677 CYP450 2C9 substrate Non-substrate 0.7319 CYP450 2D6 substrate Non-substrate 0.7662 CYP450 3A4 substrate Substrate 0.6154 CYP450 1A2 substrate Non-inhibitor 0.8458 CYP450 2C9 inhibitor Non-inhibitor 0.8889 CYP450 2D6 inhibitor Non-inhibitor 0.9036 CYP450 2C19 inhibitor Non-inhibitor 0.8401 CYP450 3A4 inhibitor Non-inhibitor 0.8293 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.921 Ames test Non AMES toxic 0.7609 Carcinogenicity Non-carcinogens 0.9189 Biodegradation Not ready biodegradable 0.8731 Rat acute toxicity 2.5731 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9778 hERG inhibition (predictor II) Non-inhibitor 0.871
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 173.3203 predictedDeepCCS 1.0 (2019) [M+H]+ 175.1452 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.75102 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:42