Chemical: Drug
scopolamine

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Overview

Generic Names
Trade 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
  • SEE
  • Scop
  • Scopamin
  • Scopine Tropate
  • Scopoderm-Tts
  • Scopolamine Bromide
  • Scopolamine Hydrobromide
  • Scopolamine Hydrobromide Trihydrate
  • Scopolamine Hyoscine
  • Scopolaminhydrobromid
  • Scopolaminium Bromide
  • Scopolammonium Bromide
  • Scopos
  • Sereen
  • Skopolamin
  • Tranaxine
  • Transcop
  • Transderm-Scop
  • Transderm-V
  • Triptone
  • Tropic Acid, Ester with Scopine
Brand Mixture Names

PharmGKB Accession Id

PA451308

Type(s):

Drug

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.

Source: Drug Bank

Indication

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

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

Mechanism of Action

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

Source: Drug Bank

Pharmacology

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.

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

Route of Elimination

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

Source: Drug Bank

Chemical Properties

Chemical Formula

C17H21NO4

Source: Drug Bank

Isomeric SMILES

CN1C2CC(CC1C3C2O3)OC(=O)[C@H](CO)c4ccccc4

Source: OpenEye

Canonical SMILES

CN1[C@H]2C[C@@H]

Source: Drug Bank

Average Molecular Weight

303.3529

Source: Drug Bank

Monoisotopic Molecular Weight

303.147058165

Source: Drug Bank

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

Source: Drug Bank

InChI String

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

Source: Drug Bank

Genes that are associated with this drug in PharmGKB's database based on (1) variant annotations, (2) literature review, (3) pathways or (4) information automatically retrieved from DrugBank, depending on the "evidence" and "source" listed below.

Drug Targets

Gene Description
CHRM1 (source: Drug Bank)
CHRM2 (source: Drug Bank)
CHRM3 (source: Drug Bank)
CHRM4 (source: Drug Bank)
CHRM5 (source: Drug Bank)
SI (source: Drug Bank)

Drug Interactions

Interaction Description
donepezil - scopolamine Possible antagonism of action (source: Drug Bank)
donepezil - scopolamine Possible antagonism of action (source: Drug Bank)
donepezil - scopolamine Possible antagonism of action (source: Drug Bank)
galantamine - scopolamine Possible antagonism of action (source: Drug Bank)
galantamine - scopolamine Possible antagonism of action (source: Drug Bank)
haloperidol - scopolamine The anticholinergic increases the risk of psychosis and tardive dyskinesia (source: Drug Bank)
haloperidol - scopolamine The anticholinergic increases the risk of psychosis and tardive dyskinesia (source: Drug Bank)
tacrine - scopolamine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Scopolamine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents. (source: Drug Bank)
tacrine - scopolamine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Scopolamine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents. (source: Drug Bank)
trimethobenzamide - scopolamine Trimethobenzamide and Scopolamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects. (source: Drug Bank)
triprolidine - scopolamine Triprolidine and Scopolamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects. (source: Drug Bank)
triprolidine - scopolamine Triprolidine and Scopolamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects. (source: Drug Bank)
trospium - scopolamine Trospium and Scopolamine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects. (source: Drug Bank)

Relationships from National Drug File - Reference Terminology (NDF-RT)

May Treat
May Prevent
Induces
Contraindicated With

LinkOuts

Web Resource:
Wikipedia
National Drug Code Directory:
0067-4345-04
DrugBank:
DB00747
ChEBI:
16794
PubChem Compound:
5184
PubChem Substance:
548858
IUPHAR Ligand:
330
Drugs Product Database (DPD):
2229868
BindingDB:
50015720
Therapeutic Targets Database:
DNC000757
FDA Drug Label at DailyMed:
4d705c57-fa98-46e0-97f3-38e1b0ada76b

Clinical Trials

These are trials that mention scopolamine and are related to either pharmacogenetics or pharmacogenomics.

No trials found.

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Sources for PharmGKB drug information: DrugBank, PubChem.