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targets (6) transporters (1)
for drugs
Identification
Name Scopolamine
Accession Number DB00747 (APRD00616)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Atrochin
  • Atroquin
  • Atroscine Hydrobromide
  • Beldavrin
  • Buscopan
  • Epoxytropine Tropate
  • Euscopol
  • Hydroscine Hydrobromide
  • Hyocine F Hydrobromide
  • Hyosceine
  • Hyoscine
  • Hyoscine Bromide
  • Hyoscine Hydrobromide
  • Hyoscyine Hydrobromide
  • Hyosol
  • Hysco
  • Isopto Hyoscine
  • Isoscopil
  • Kwells
  • L-Hyoscine Hydrobromide
  • L-Scopolamine
  • Methscopolamine Bromide
  • Oscine
  • Scop
  • Scopamin
  • Scopine Tropate
  • Scopoderm-Tts
  • Scopolamine Bromide
  • Scopolamine Hydrobromide
  • Scopolamine Hydrobromide Trihydrate
  • Scopolamine Hyoscine
  • Scopolaminhydrobromid
  • Scopolaminium Bromide
  • Scopolammonium Bromide
  • Scopos
  • SEE
  • Sereen
  • Skopolamin
  • Tranaxine
  • Transcop
  • Transderm-Scop
  • Transderm-V
  • Triptone
  • Tropic Acid, Ester with Scopine
Brand name mixtures Not Available
Categories
  • Mydriatics
  • Adjuvants, Anesthesia
  • Muscarinic Antagonists
  • Antispasmodics
  • Cholinergic Antagonists
  • Antimuscarinics
  • Adjuvants
CAS number 6533-68-2
Weight Average: 303.3529
Monoisotopic: 303.147058165
Chemical Formula C17H21NO4
InChI Key InChIKey=STECJAGHUSJQJN-UHFFFAOYSA-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
Plain Text
IUPAC Name
9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl 3-hydroxy-2-phenylpropanoate
SMILES
CN1C2CC(CC1C1OC21)OC(=O)C(CO)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenylacetates
  • Tropanes
  • Alkaloids and Alkaloid Derivatives
Substructures
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Acetates
  • Phenylacetates
  • Pyrrolidines
  • Ethers
  • Benzene and Derivatives
  • Alcohols and Polyols
  • Aliphatic and Aryl Amines
  • Heterocyclic compounds
  • Aromatic compounds
  • Tropanes
  • Morpholines
  • Alkaloids and Alkaloid Derivatives
  • Epoxides
  • Piperidines
Pharmacology
Indication For the treatment of excessive salivation, colicky abdominal pain, bradycardia, sialorrhoea, diverticulitis, irritable bowel syndrome and motion sickness.
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).
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Less than 10% of the total dose is excreted in the urine as parent and metabolites over 108 hours.
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Boca pharmacal inc
  • Private formulations inc
Packagers
Dosage forms
Form Route Strength
Disc Transdermal
Liquid Intravenous
Solution Intramuscular
Solution Intravenous
Tablet Oral
Prices
Unit description Cost Unit
Oscion Cleanser 6% Lotion 340.2 gm Bottle 88.56 USD bottle
Oscion Cleanser 3% Lotion 340.2 gm Bottle 85.69 USD bottle
Isopto Hyoscine 0.25% Solution 5ml Bottle 30.99 USD bottle
Transderm-Scop 1.5 mg (1 Box Contains 4 Patches) 14.87 USD patch
Transderm-Scop 1.5 mg (1 Box Contains 10 Patches) 12.04 USD patch
Transderm-scop 1.5 mg/72hr 12.01 USD each
Scopolamine hbr crystals 6.86 USD g
Isopto hyoscine 0.25% drops 5.59 USD ml
Scopolamine 0.4 mg/ml vial 5.4 USD ml
Buscopan 20 mg/ml 4.5 USD ml
Pamine forte 5 mg tablet 3.9 USD tablet
Pamine 2.5 mg tablet 2.66 USD tablet
Methscopolamine Bromide 5 mg tablet 2.17 USD tablet
Methscopolamine brom 5 mg tablet 2.09 USD tablet
Methscopolamine Bromide 2.5 mg tablet 1.67 USD tablet
Methscopolamine brom 2.5 mg tablet 1.61 USD tablet
Scopace 0.4 mg tablet 0.67 USD tablet
Buscopan 10 mg Tablet 0.34 USD tablet
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 0.8 PhysProp
Caco2 permeability -4.93 [ADME Research, USCD] BiGG
Predicted Properties
Property Value Source
water solubility 6.61e+00 g/l ALOGPS
logP 1.40 ALOGPS
logP 0.89 ChemAxon Molconvert
logS -1.66 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 62.30 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 79.72 ChemAxon Molconvert
polarizability 30.95 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 5184 Link_out
PubChem Substance 46506966 Link_out
ChemSpider 4997 Link_out
BindingDB 50015720 Link_out
ChEBI 16794 Link_out
ChEMBL 16794 Link_out
Therapeutic Targets Database DNC000757 Link_out
Drug Product Database 2229868 Link_out
Drugs.com http://www.drugs.com/cdi/scopolamine-drops.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Scopolamine Link_out
ATC Codes
  • A04AD01
  • N05CM05
  • S01FA02
  • A03BB03
  • S01FA03
  • A03BB01
AHFS Codes
  • 12:08.08
PDB Entries Not Available
FDA label show (686 KB)
MSDS show (73.6 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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. Epub 2010 Apr 14. Pubmed

2. Sucrase-isomaltase, intestinal

Pharmacological action: unknown
Actions: inhibitor

Plays an important role in the final stage of carbohydrate digestion

Organism class: human
UniProt ID: P14410 Link_out
Gene: SI Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2010 Mar 15. Pubmed

3. Muscarinic acetylcholine receptor M2

Pharmacological action: unknown
Actions: antagonist

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

Organism class: human
UniProt ID: P08172 Link_out
Gene: CHRM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

4. Muscarinic acetylcholine receptor M3

Pharmacological action: unknown
Actions: antagonist

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

Organism class: human
UniProt ID: P20309 Link_out
Gene: CHRM3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

5. Muscarinic acetylcholine receptor M4

Pharmacological action: unknown
Actions: antagonist

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

Organism class: human
UniProt ID: P08173 Link_out
Gene: CHRM4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

6. Muscarinic acetylcholine receptor M5

Pharmacological action: unknown
Actions: antagonist

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

Organism class: human
UniProt ID: P08912 Link_out
Gene: CHRM5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Transporters

1. Multidrug resistance protein 1

Actions: inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:06

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.