Identification

Name
Scopolamine
Accession Number
DB00747  (APRD00616)
Type
Small Molecule
Groups
Approved, Investigational
Description

An alkaloid from Solanaceae, especially Datura metel L. and Scopola carniolica. Scopolamine and its quaternary derivatives act as antimuscarinics like atropine, but may have more central nervous system effects. Among the many uses are as an anesthetic premedication, in urinary incontinence, in motion sickness, as an antispasmodic, and as a mydriatic and cycloplegic. [PubChem]

Structure
Thumb
Synonyms
  • (-)-hyoscine
  • (-)-scopolamine
  • (1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoate
  • 6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropate
  • 6,7-Epoxytropine tropate
  • alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester
  • Hyoscine
  • scopine (-)-tropate
  • scopine (−)-tropate
  • Scopolamine hydrobromide
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Scopolamine Hydrobromide InjectionLiquid0.4 mgIntramuscular; Intravenous; SubcutaneousOmega Laboratories Ltd2008-05-31Not applicableCanada
Scopolamine Hydrobromide InjectionLiquid0.6 mgIntramuscular; Intravenous; SubcutaneousOmega Laboratories Ltd2008-07-08Not applicableCanada
Scopolamine Hydrobromide Injection USPSolution0.6 mgIntramuscular; Intravenous; SubcutaneousPfizer1981-12-31Not applicableCanada
Scopolamine Hydrobromide Injection USPSolution0.4 mgIntramuscular; Intravenous; SubcutaneousPfizer1981-12-31Not applicableCanada
Transderm ScopPatch, extended release1 mg/3dTransdermalNovartis2007-10-02Not applicableUs
Transderm ScopPatch, extended release1 mg/3dTransdermalBaxter Laboratories2016-12-01Not applicableUs
Transderm ScopPatch, extended release1 mg/3dTransdermalPhysicians Total Care, Inc.2007-10-02Not applicableUs
Transderm ScopPatch, extended release1 mg/3dTransdermalSandoz2016-12-01Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Scopolamine Trandermal SystemPatch, extended release1 mg/1TransdermalPerrigo New York Inc.2017-06-13Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Diban CapScopolamine (3.3 mcg) + Atropine Sulfate (9.7 mcg) + Attapulgite (300 mg) + Hyoscyamine sulfate (0.0519 mg) + Opium (12 mg) + Pectin (71.4 mg)CapsuleOralWyeth Ayerst Canada Inc.1998-02-182001-01-30Canada
Diban CapScopolamine (3.3 mcg) + Atropine Sulfate (9.7 mcg) + Attapulgite (300 mg) + Hyoscyamine sulfate (0.0519 mg) + Opium (12 mg) + Pectin (71.4 mg)CapsuleOralAyerst Laboratories1992-12-311999-04-12Canada
Donnagel LiqScopolamine (6.5 mcg) + Atropine Sulfate (0.0194 mg) + Hyoscyamine sulfate (0.1037 mg) + Kaolin (6 g) + Pectin (142.8 mg)LiquidOralWyeth Ayerst Canada Inc.1995-12-311997-08-14Canada
Donnagel LiqScopolamine (6.5 mcg) + Atropine Sulfate (0.0194 mg) + Hyoscyamine sulfate (0.1037 mg) + Kaolin (6 g) + Pectin (142.8 mg)LiquidOralAyerst Laboratories1993-12-311996-09-10Canada
Donnatal ElixirScopolamine (6.5 mcg) + Atropine Sulfate (0.0194 mg) + Hyoscyamine sulfate (0.1037 mg) + Phenobarbital (16.2 mg)ElixirOralAyerst Laboratories1991-12-311996-09-10Canada
Donnatal ElixirScopolamine (6.5 mcg) + Atropine Sulfate (0.0194 mg) + Hyoscyamine sulfate (0.1037 mg) + Phenobarbital (16.2 mg)ElixirOralWyeth Ayerst Canada Inc.1994-12-312001-01-16Canada
Donnatal ExtentabsScopolamine (0.0195 mg) + Atropine Sulfate (0.0582 mg) + Hyoscyamine sulfate (0.3111 mg) + Phenobarbital (48.6 mg)Tablet, extended releaseOralAyerst Laboratories1991-12-311996-09-10Canada
Donnatal Extentabs SrtScopolamine (0.0195 mg) + Atropine Sulfate (0.0582 mg) + Hyoscyamine sulfate (0.3111 mg) + Phenobarbital (48.6 mg)Tablet, extended releaseOralWyeth Ayerst Canada Inc.1994-12-312001-05-07Canada
Donnatal TabScopolamine (6.5 mcg) + Atropine Sulfate (0.0194 mg) + Hyoscyamine sulfate (0.1037 mg) + Phenobarbital (16.2 mg)TabletOralWyeth Ayerst Canada Inc.1994-12-312001-05-22Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Atenolol ScopolamineScopolamine (.25 mg/25.25mg) + Atenolol (25 mg/25.25mg)TabletBuccal; Oral; Sublingual; TransmucosalTPS2014-10-01Not applicableUs
Atenolol ScopolamineScopolamine (.5 mg/50.5mg) + Atenolol (50 mg/50.5mg)TabletOralTPS2014-10-01Not applicableUs
B-DonnaScopolamine (0.0065 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1)TabletOralWinder Laboratories, LLC2015-12-302016-03-03Us
Belladonna Alkaloids with PhenobarbitalScopolamine (0.0065 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1)TabletOralbryant ranch prepack1966-01-012015-05-01Us
Belladonna Alkaloids with PhenobarbitalScopolamine (0.0065 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1)TabletOralWest-Ward Pharmaceuticals Corp1966-01-01Not applicableUs0143 114020170720 1564 4ev749
Belladonna Alkaloids with PhenobartbitalScopolamine (0.0065 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1)TabletOralApace Packaging2000-12-012015-01-31Us
Belladonna Alkaloids with PhenobartbitalScopolamine (0.0065 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1)TabletOralLegacy Pharmaceutical Packaging2000-12-01Not applicableUs
Belladonna Alkaloids with PhenobartbitalScopolamine (0.0065 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1)TabletOralLiberty Pharmaceuticals, Inc.2000-12-01Not applicableUs00143 1140 10 nlmimage10 bb045dd2
Belladonna Alkaloids with PhenobartbitalScopolamine (0.0065 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1)TabletOralRebel Distributors2004-08-31Not applicableUs
Belladonna Alkaloids with PhenobartbitalScopolamine (0.0065 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1)TabletOralPreferreed Pharmaceuticals Inc.2004-08-312013-04-30Us
International/Other Brands
Scopoderm / Transderm-Scop (Novartis)
Categories
UNII
DL48G20X8X
CAS number
51-34-3
Weight
Average: 303.3529
Monoisotopic: 303.147058165
Chemical Formula
C17H21NO4
InChI Key
STECJAGHUSJQJN-FWXGHANASA-N
InChI
InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1
IUPAC Name
(1R,2R,4S,5S,7R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate
SMILES
CN1[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1

Pharmacology

Indication

For the treatment of excessive salivation, colicky abdominal pain, bradycardia, sialorrhoea, diverticulitis, irritable bowel syndrome and motion sickness.

Associated Conditions
Associated Therapies
Pharmacodynamics

Scopolamine 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. Scopolamine has many uses including the prevention of motion sickness. It is not clear how Scopolamine 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 Scopolamine prevents communication between the nerves of the vestibule and the vomiting center in the brain by blocking the action of acetylcholine. Scopolamine also may work directly on the vomiting center. Scopolamine must be taken before the onset of motion sickness to be effective.

Mechanism of action

Scopolamine acts by interfering with the transmission of nerve impulses by acetylcholine in the parasympathetic nervous system (specifically the vomiting center).

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Human
USucrase-isomaltase, intestinal
inhibitor
Human
UMuscarinic acetylcholine receptor M2
antagonist
Human
UMuscarinic acetylcholine receptor M3
antagonist
Human
UMuscarinic acetylcholine receptor M4
antagonist
Human
UMuscarinic acetylcholine receptor M5
antagonist
Human
UNeuronal acetylcholine receptor subunit alpha-4Not AvailableHuman
UNeuronal acetylcholine receptor subunit beta-2Not AvailableHuman
Absorption

Bioavailability is 10 - 50%

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

Less than 10% of the total dose is excreted in the urine as parent and metabolites over 108 hours.

Half life

4.5 hours

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(2-benzhydryloxyethyl)diethyl-methylammonium iodideThe risk or severity of adverse effects can be increased when Scopolamine is combined with (2-benzhydryloxyethyl)diethyl-methylammonium iodide.
1,10-PhenanthrolineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Scopolamine is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Scopolamine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Scopolamine.
Food Interactions
Not Available

References

Synthesis Reference

Yang Guodong, "Preparation and application of scopolamine and chlorpromazine as a drug-withdrawal agent." U.S. Patent US5543407, issued February, 1993.

US5543407
General References
  1. Putcha L, Cintron NM, Tsui J, Vanderploeg JM, Kramer WG: Pharmacokinetics and oral bioavailability of scopolamine in normal subjects. Pharm Res. 1989 Jun;6(6):481-5. [PubMed:2762223]
External Links
Human Metabolome Database
HMDB0003573
KEGG Drug
D00138
KEGG Compound
C01851
PubChem Compound
3000322
PubChem Substance
46506966
ChemSpider
10194106
BindingDB
50015720
ChEBI
16794
ChEMBL
CHEMBL569713
Therapeutic Targets Database
DNC000757
PharmGKB
PA451308
IUPHAR
330
Guide to Pharmacology
GtP Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Scopolamine
ATC Codes
A04AD01 — ScopolamineS01FA02 — ScopolamineN05CM05 — ScopolamineA04AD51 — Scopolamine, combinations
AHFS Codes
  • 12:08.08 — Antimuscarinics Antispasmodics
FDA label
Download (686 KB)
MSDS
Download (73.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingPreventionAlzheimer's Disease (AD) / Dementias1
1Active Not RecruitingBasic ScienceHealthy Volunteers1
1Active Not RecruitingTreatmentAlzheimer's Disease (AD)1
1CompletedNot AvailableHealthy Volunteers1
1CompletedDiagnosticUsing Copolamine Butylbromide in Probe-based Confocal Laser Endomicroscopy for Gastroendoscopy Examination1
1CompletedTreatmentAlzheimer's Disease (AD) / Memory Disturbances1
1CompletedTreatmentDementias1
1RecruitingBasic ScienceHealthy Volunteers1
1RecruitingTreatmentSocial Anxiety Disorder (SAD)1
1, 2CompletedTreatmentSialorrhea1
2CompletedPreventionMotion Sickness1
2Not Yet RecruitingTreatmentAnalgesia, Obstetrical1
2TerminatedTreatmentDepression, Bipolar / Unipolar Depression1
2, 3CompletedNot AvailableLabour Pain1
2, 3TerminatedTreatmentMotion Sickness1
4CompletedBasic ScienceHealthy Volunteers1
4Not Yet RecruitingTreatmentPatients1
4RecruitingOtherDrug Reaction1
4RecruitingPreventionLaparoscopic Sleeve Gastrectomy / Post-Operative Nausea and Vomiting (PONV)1
4RecruitingPreventionNausea / Satisfaction / Vomiting1
4RecruitingTreatmentDepression1
4RecruitingTreatmentMajor Depressive Disorder (MDD)1
Not AvailableCompletedNot AvailableCholinergic Function1
Not AvailableCompletedNot AvailableRhytidoplasty1
Not AvailableCompletedDiagnosticAD1
Not AvailableCompletedPreventionPost-Operative Nausea and Vomiting (PONV)1
Not AvailableCompletedSupportive CareNausea / Vomiting1
Not AvailableCompletedTreatmentNausea / Vomiting1
Not AvailableRecruitingDiagnosticGastrointestinal Imaging With pCLE1
Not AvailableUnknown StatusPreventionSimulator Sickness1
Not AvailableUnknown StatusTreatmentDepression1
Not AvailableWithdrawnTreatmentMajor Depressive Disorder (MDD)1

Pharmacoeconomics

Manufacturers
  • Boca pharmacal inc
  • Private formulations inc
Packagers
  • A. Aarons Inc.
  • Adamis Laboratories
  • Advanced Pharmaceutical Services Inc.
  • Alcon Laboratories
  • Alza Corp.
  • Amend
  • Apace Packaging
  • Apotheca Inc.
  • APP Pharmaceuticals
  • Aristos Pharmaceuticals
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Auriga Pharmaceuticals LLC
  • Bausch & Lomb Inc.
  • Baxter International Inc.
  • Boca Pharmacal
  • Bradley Pharmaceuticals Inc.
  • Breckenridge Pharmaceuticals
  • Bryant Ranch Prepack
  • Burel Pharmaceuticals Inc.
  • C.O. Truxton Inc.
  • Carwin Associates Inc.
  • Central Texas Community Health Centers
  • Contract Pharm
  • Cornerstone Pharmacy
  • Corvit Pharmaceuticals
  • Dexo LLC
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Excellium Pharmaceutical Inc.
  • H.J. Harkins Co. Inc.
  • Hawthorn Pharmaceuticals
  • Hope Pharmaceuticals
  • Irisys Inc.
  • Kaiser Foundation Hospital
  • Kenwood Labs
  • Kraft Pharmaceutical Co. Inc.
  • Kylemore Pharmaceuticals
  • Larken Laboratories Inc.
  • Liberty Pharmaceuticals
  • Llorens Pharmaceutical
  • Magna Pharmaceuticals
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medi Rx Pharmaceutical Inc.
  • Mikart Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nexgen Pharma Inc.
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Patient First Corp.
  • PBM Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Provident Pharmaceuticals LLC
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • River's Edge Pharmaceuticals
  • Sandhills Packaging Inc.
  • SJ Pharmaceuticals LLC
  • Southwood Pharmaceuticals
  • Sovereign Pharmaceuticals Ltd.
  • Trigen Laboratories Inc.
  • United Research Laboratories Inc.
  • Veratex Corp.
  • Vintage Pharmaceuticals Inc.
  • Vision Pharma LLC
  • West-Ward Pharmaceuticals
Dosage forms
FormRouteStrength
TabletBuccal; Oral; Sublingual; Transmucosal
CapsuleOral
LiquidOral
ElixirOral
Tablet, extended releaseOral
Tablet, film coated, extended releaseOral
TabletOral
SolutionOphthalmic2.5 mg/1mL
Tablet, solubleOral0.4 mg/1
Injection, solutionIntramuscular; Intravenous; Subcutaneous0.4 mg/1mL
LiquidIntramuscular; Intravenous; Subcutaneous0.4 mg
LiquidIntramuscular; Intravenous; Subcutaneous0.6 mg
SolutionIntramuscular; Intravenous; Subcutaneous0.4 mg
SolutionIntramuscular; Intravenous; Subcutaneous0.6 mg
Patch, extended releaseTransdermal1 mg/1
Patch, extended releaseTransdermal1 mg/3d
Prices
Unit descriptionCostUnit
Oscion Cleanser 6% Lotion 340.2 gm Bottle88.56USD bottle
Oscion Cleanser 3% Lotion 340.2 gm Bottle85.69USD bottle
Isopto Hyoscine 0.25% Solution 5ml Bottle30.99USD bottle
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
Scopolamine hbr crystals6.86USD g
Isopto hyoscine 0.25% drops5.59USD ml
Scopolamine 0.4 mg/ml vial5.4USD ml
Buscopan 20 mg/ml4.5USD ml
Pamine forte 5 mg tablet3.9USD tablet
Pamine 2.5 mg tablet2.66USD tablet
Methscopolamine Bromide 5 mg tablet2.17USD tablet
Methscopolamine brom 5 mg tablet2.09USD tablet
Methscopolamine Bromide 2.5 mg tablet1.67USD tablet
Methscopolamine brom 2.5 mg tablet1.61USD tablet
Scopace 0.4 mg tablet0.67USD tablet
Buscopan 10 mg Tablet0.34USD 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)59 °CPhysProp
water solubility1E+005 mg/LYALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.98SANGSTER (1994)
Caco2 permeability-4.93ADME Research, USCD
pKa7.75 (at 25 °C)SANGSTER,J (1994)
Predicted Properties
PropertyValueSource
Water Solubility6.61 mg/mLALOGPS
logP1.4ALOGPS
logP0.89ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)6.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area62.3 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.72 m3·mol-1ChemAxon
Polarizability31.41 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9615
Blood Brain Barrier+0.8218
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.5174
P-glycoprotein inhibitor INon-inhibitor0.87
P-glycoprotein inhibitor IINon-inhibitor0.8623
Renal organic cation transporterInhibitor0.531
CYP450 2C9 substrateNon-substrate0.7002
CYP450 2D6 substrateNon-substrate0.7296
CYP450 3A4 substrateSubstrate0.5253
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.927
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9581
BiodegradationNot ready biodegradable0.9073
Rat acute toxicity2.0907 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9378
hERG inhibition (predictor II)Non-inhibitor0.9167
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
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0009000000-9733effdc3262b114ed6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0809000000-a686e4c768aedb57cf8e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-1901000000-f66f538c7db471e86fd5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-3900000000-5eedeba4bedea55de9ad
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udr-7900000000-1309364bbca3810a6afa
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-0900000000-1c1d2f52fb7a5d745e1e

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
Piperidines / Benzene and substituted derivatives / Morpholines / N-alkylpyrrolidines / Trialkylamines / Amino acids and derivatives / Carboxylic acid esters / Azacyclic compounds / Oxacyclic compounds / Dialkyl ethers
show 7 more
Substituents
Beta-hydroxy acid / Monocyclic benzene moiety / Morpholine / Oxazinane / Piperidine / N-alkylpyrrolidine / Benzenoid / Pyrrolidine / Amino acid or derivatives / Carboxylic acid ester
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, epoxide, propanoate ester, tropane alkaloid (CHEBI:16794)

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. Murasaki O, Kaibara M, Nagase Y, Mitarai S, Doi Y, Sumikawa K, Taniyama K: Site of action of the general anesthetic propofol in muscarinic M1 receptor-mediated signal transduction. J Pharmacol Exp Ther. 2003 Dec;307(3):995-1000. Epub 2003 Oct 8. [PubMed:14534362]
  2. Klinkenberg I, Blokland A: The validity of scopolamine as a pharmacological model for cognitive impairment: a review of animal behavioral studies. Neurosci Biobehav Rev. 2010 Jul;34(8):1307-50. doi: 10.1016/j.neubiorev.2010.04.001. Epub 2010 Apr 14. [PubMed:20398692]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sucrose alpha-glucosidase activity
Specific Function
Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name
SI
Uniprot ID
P14410
Uniprot Name
Sucrase-isomaltase, intestinal
Molecular Weight
209451.49 Da
References
  1. Minai-Tehrani D, Fooladi N, Minoui S, Sobhani-Damavandifar Z, Aavani T, Heydarzadeh S, Attar F, Ghaffari M, Nazem H: Structural changes and inhibition of sucrase after binding of scopolamine. Eur J Pharmacol. 2010 Jun 10;635(1-3):23-6. doi: 10.1016/j.ejphar.2010.02.040. Epub 2010 Mar 15. [PubMed:20230815]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. Johnson DE, Nedza FM, Spracklin DK, Ward KM, Schmidt AW, Iredale PA, Godek DM, Rollema H: The role of muscarinic receptor antagonism in antipsychotic-induced hippocampal acetylcholine release. Eur J Pharmacol. 2005 Jan 4;506(3):209-19. Epub 2004 Dec 15. [PubMed:15627430]
  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. Reitz AB, Gupta SK, Huang Y, Parker MH, Ryan RR: The preparation and human muscarinic receptor profiling of oxybutynin and N-desethyloxybutynin enantiomers. Med Chem. 2007 Nov;3(6):543-5. [PubMed:18045203]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor 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
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. Reitz AB, Gupta SK, Huang Y, Parker MH, Ryan RR: The preparation and human muscarinic receptor profiling of oxybutynin and N-desethyloxybutynin enantiomers. Med Chem. 2007 Nov;3(6):543-5. [PubMed:18045203]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
References
  1. Reitz AB, Gupta SK, Huang Y, Parker MH, Ryan RR: The preparation and human muscarinic receptor profiling of oxybutynin and N-desethyloxybutynin enantiomers. Med Chem. 2007 Nov;3(6):543-5. [PubMed:18045203]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Smulders CJ, Zwart R, Bermudez I, van Kleef RG, Groot-Kormelink PJ, Vijverberg HP: Cholinergic drugs potentiate human nicotinic alpha4beta2 acetylcholine receptors by a competitive mechanism. Eur J Pharmacol. 2005 Feb 21;509(2-3):97-108. [PubMed:15733544]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNB2
Uniprot ID
P17787
Uniprot Name
Neuronal acetylcholine receptor subunit beta-2
Molecular Weight
57018.575 Da
References
  1. Smulders CJ, Zwart R, Bermudez I, van Kleef RG, Groot-Kormelink PJ, Vijverberg HP: Cholinergic drugs potentiate human nicotinic alpha4beta2 acetylcholine receptors by a competitive mechanism. Eur J Pharmacol. 2005 Feb 21;509(2-3):97-108. [PubMed:15733544]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2018 20:26