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Identification
NameScopolamine
Accession NumberDB00747  (APRD00616)
TypeSmall Molecule
GroupsApproved
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
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Scopolamine Hydrobromide Injectionliquid0.6 mgintramuscular; intravenous; subcutaneousOmega Laboratories Ltd2008-07-08Not applicableCanada
Scopolamine Hydrobromide Injectionliquid0.4 mgintramuscular; intravenous; subcutaneousOmega Laboratories Ltd2008-05-31Not applicableCanada
Scopolamine Hydrobromide Injection 0.4mg/mlsolution.4 mgintramuscular; intravenous; subcutaneousHospira Healthcare Corporation1981-12-31Not applicableCanada
Scopolamine Hydrobromide Injection 0.6mg/mlsolution.6 mgintramuscular; intravenous; subcutaneousHospira Healthcare Corporation1981-12-31Not applicableCanada
Transderm Scoppatch, extended release1 mg/3dtransdermalNovatris Consumer Health, Inc.2007-10-02Not applicableUs
Transderm Scoppatch, extended release1 mg/3dtransdermalPhysicians Total Care, Inc.2007-10-02Not applicableUs
Transderm Scoppatch, extended release1 mg/3dtransdermalBaxter Healthcare Corporation2003-01-01Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Scopolamine Hydrobromideinjection, solution.4 mg/mLintramuscular; intravenous; subcutaneousAPP Pharmaceuticals, LLC2000-10-18Not applicableUs
International Brands
NameCompany
ScopodermNot Available
Transderm-ScopNovartis
Brand mixtures
NameLabellerIngredients
Atenolol ScopolamineTps
B-donnaWinder Laboratories, LLC
Belladonna Alkaloids With PhenobartbitalLiberty Pharmaceuticals, Inc.
Diban CapAyerst Laboratories
Donnagel LiqAyerst Laboratories
DonnatalKAISER FOUNDATION HOSPITALS
Donnatal ElixirAyerst Laboratories
Donnatal ExtentabsPBM Pharmaceuticals, Inc
Donnatal Extentabs SrtWyeth Ayerst Canada Inc.
Donnatal TabWyeth Ayerst Canada Inc.
Me-PB-hyosMethod Pharmaceuticals, Llc
PhenohytroWinder Laboratories, LLC
Propranolol ScopolamineTps
QuadrapaxRebel Distributors Corp
Re-PB Hyos ElixirKAISER FOUNDATION HOSPITALS
Se-donna Pb HyosSeton Pharmaceuticals
SaltsNot Available
Categories
UNIIDL48G20X8X
CAS number51-34-3
WeightAverage: 303.3529
Monoisotopic: 303.147058165
Chemical FormulaC17H21NO4
InChI KeyInChIKey=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[[email protected]]2C[C@@H](C[C@@H]1[[email protected]]1O[C@@H]21)OC(=O)[[email protected]](CO)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Beta-hydroxy acid
  • N-alkylpyrrolidine
  • Piperidine
  • Oxazinane
  • Morpholine
  • Hydroxy acid
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of excessive salivation, colicky abdominal pain, bradycardia, sialorrhoea, diverticulitis, irritable bowel syndrome and motion sickness.
PharmacodynamicsScopolamine 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 actionScopolamine acts by interfering with the transmission of nerve impulses by acetylcholine in the parasympathetic nervous system (specifically the vomiting center).
Related Articles
AbsorptionBioavailability is 10 - 50%
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationLess than 10% of the total dose is excreted in the urine as parent and metabolites over 108 hours.
Half life4.5 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Boca pharmacal inc
  • Private formulations inc
Packagers
Dosage forms
FormRouteStrength
Tabletbuccal; oral; sublingual; transmucosal
Capsuleoral
Liquidoral
Tabletoral
Tablet (extended-release)oral
Tablet, film coated, extended releaseoral
Elixiroral
Injection, solutionintramuscular; intravenous; subcutaneous.4 mg/mL
Liquidintramuscular; intravenous; subcutaneous0.4 mg
Liquidintramuscular; intravenous; subcutaneous0.6 mg
Solutionintramuscular; intravenous; subcutaneous.4 mg
Solutionintramuscular; intravenous; subcutaneous.6 mg
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point59 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot 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
ATC CodesA04AD01A04AD51N05CM05S01FA02
AHFS Codes
  • 12:08.08
PDB EntriesNot Available
FDA labelDownload (686 KB)
MSDSDownload (73.6 KB)
Interactions
Drug Interactions
Drug
AclidiniumAclidinium may increase the anticholinergic activities of Scopolamine.
AzelastineScopolamine may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Scopolamine.
Botulinum Toxin Type AScopolamine may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BScopolamine may increase the anticholinergic activities of Botulinum Toxin Type B.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
BuprenorphineScopolamine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
Cimetropium BromideScopolamine may increase the anticholinergic activities of Cimetropium Bromide.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
EluxadolineScopolamine may increase the activities of Eluxadoline.
EthanolScopolamine may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Scopolamine is combined with Glucagon recombinant.
HydrocodoneScopolamine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Scopolamine.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Scopolamine.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Scopolamine.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
MethotrimeprazineScopolamine may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MetyrosineScopolamine may increase the sedative activities of Metyrosine.
MianserinMianserin may increase the anticholinergic activities of Scopolamine.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
MirabegronThe risk or severity of adverse effects can be increased when Scopolamine is combined with Mirabegron.
MirtazapineScopolamine may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
MorphineThe risk or severity of adverse effects can be increased when Scopolamine is combined with Morphine.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
OrphenadrineScopolamine may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
ParaldehydeScopolamine may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Scopolamine is combined with Paroxetine.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
Potassium ChlorideScopolamine may increase the ulcerogenic activities of Potassium Chloride.
PramipexoleScopolamine may increase the sedative activities of Pramipexole.
PramlintidePramlintide may increase the anticholinergic activities of Scopolamine.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Scopolamine.
RamosetronScopolamine may increase the activities of Ramosetron.
RopiniroleScopolamine may increase the sedative activities of Ropinirole.
RotigotineScopolamine may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Scopolamine.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Scopolamine.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Scopolamine.
SuvorexantScopolamine may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TacrineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Tacrine.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Scopolamine.
ThalidomideScopolamine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TiotropiumScopolamine may increase the anticholinergic activities of Tiotropium.
TopiramateThe risk or severity of adverse effects can be increased when Scopolamine is combined with Topiramate.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Scopolamine.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Scopolamine.
ZolpidemScopolamine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
Food InteractionsNot 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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
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
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 action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
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 action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
Gene Name:
CHRM4
Uniprot ID:
P08173
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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM5
Uniprot ID:
P08912
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 ]

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
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on November 10, 2015 13:45