Methscopolamine bromide

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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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
Humans
AMuscarinic acetylcholine receptor M2
antagonist
Humans
UMuscarinic acetylcholine receptor M3
antagonist
Humans
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
Medicalerrors
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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
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
1,2-Benzodiazepine1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Methscopolamine bromide.
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Methscopolamine bromide.
AcetophenazineAcetophenazine may increase the central nervous system depressant (CNS depressant) activities of Methscopolamine bromide.
AclidiniumThe risk or severity of adverse effects can be increased when Methscopolamine bromide is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Methscopolamine bromide is combined with Adenosine.
AgomelatineAgomelatine may increase the central nervous system depressant (CNS depressant) activities of Methscopolamine bromide.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Methscopolamine bromide.
AlimemazineAlimemazine may increase the central nervous system depressant (CNS depressant) activities of Methscopolamine bromide.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Methscopolamine bromide.
AlmotriptanAlmotriptan may increase the central nervous system depressant (CNS depressant) activities of Methscopolamine bromide.
Interactions
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Food Interactions
  • Take before a meal. Take methscopolamine bromide 30 minutes before meals and at bedtime for optimal therapeutic effect.

Products

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Active Moieties
NameKindUNIICASInChI Key
MethscopolamineionicVDR09VTQ8U13265-10-6LZCOQTDXKCNBEE-IKIFYQGPSA-N
Product Images
International/Other Brands
Pamine
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Methscopolamine BromideTablet5 mg/1OralFougera Pharmaceuticals Inc.2009-10-222013-12-31US flag
Methscopolamine BromideTablet2.5 mg/1OralFougera Pharmaceuticals Inc.2009-10-222013-12-31US flag
PamineTablet2.5 mg/1OralPharma Derm, A Division Of Fougera Pharmaceuticals Inc.1953-04-092013-12-31US flag
PamineTablet2.5 mg/1OralPharma Derm, A Division Of Fougera Pharmaceuticals Inc.1953-04-09Not applicableUS flag
Pamine ForteTablet5 mg/1OralPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2003-03-25Not applicableUS flag
Pamine ForteTablet5 mg/1OralPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2003-03-252013-12-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MethscopolamineTablet5 mg/1OralGolden State Medical Supply, Inc.2006-12-282017-01-02US flag64376 0604 61 nlmimage10 f608fb57
Methscopolamine BromideTablet2.5 mg/1OralPar Pharmaceutical2006-12-28Not applicableUS flag
Methscopolamine BromideTablet5 mg/1OralPD-Rx Pharmaceuticals, Inc.2013-10-01Not applicableUS flag
Methscopolamine BromideTablet5 mg/1OralBayshore Pharmaceuticals LLC2013-10-01Not applicableUS flag
Methscopolamine BromideTablet5 mg/1OralE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2011-07-27Not applicableUS flag
Methscopolamine BromideTablet5 mg/1OralBreckenridge Pharmaceutical, Inc.2012-05-21Not applicableUS flag
Methscopolamine BromideTablet2.5 mg/1OralBayshore Pharmaceuticals LLC2013-10-01Not applicableUS flag
Methscopolamine BromideTablet5 mg/1OralPar Pharmaceutical2006-12-28Not applicableUS flag
Methscopolamine BromideTablet2.5 mg/1OralPD-Rx Pharmaceuticals, Inc.2013-10-01Not applicableUS flag
Methscopolamine BromideTablet2.5 mg/1OralE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2011-03-16Not applicableUS flag

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
Human Metabolome Database
HMDB0014605
KEGG Drug
D00715
PubChem Compound
23724781
PubChem Substance
46506260
ChemSpider
10481908
RxNav
56092
ChEBI
61276
ChEMBL
CHEMBL1354199
Therapeutic Targets Database
DAP001126
PharmGKB
PA164784032
Wikipedia
Methylscopolamine_bromide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Nycomed us inc
  • Novartis consumer health inc
Packagers
  • A. Aarons Inc.
  • Kenwood Labs
  • Novartis AG
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 Area59.06 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity95.63 m3·mol-1ChemAxon
Polarizability33.35 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
Not Available

Targets

Drugtargets
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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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [Article]
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
  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. [Article]
  2. 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
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. [Article]
  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. [Article]
  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. [Article]

Drug created on June 13, 2005 13:24 / Updated on March 04, 2021 11:13