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Showing drug card for Scopolamine (DB00747)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:07:55
Primary Accession Number DB00747
Secondary Accession Number
  • APRD00616
Name Scopolamine
Drug Type
  • Approved
  • Small Molecule
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]
Synonyms Not Available
Brand Names
  1. Atrochin
  2. Atroquin
  3. Atroscine Hydrobromide
  4. Beldavrin
  5. Buscopan
  6. Epoxytropine Tropate
  7. Euscopol
  8. Hydroscine Hydrobromide
  9. Hyocine F Hydrobromide
  10. Hyosceine
  11. Hyoscine
  12. Hyoscine Bromide
  13. Hyoscine Hydrobromide
  14. Hyoscyine Hydrobromide
  15. Hyosol
  16. Hysco
  17. Isopto Hyoscine
  18. Isoscopil
  19. Kwells
  20. L-Hyoscine Hydrobromide
  21. L-Scopolamine
  22. Methscopolamine Bromide
  23. Oscine
  24. SEE
  25. Scop
  26. Scopamin
  27. Scopine Tropate
  28. Scopoderm-Tts
  29. Scopolamine Bromide
  30. Scopolamine Hydrobromide
  31. Scopolamine Hydrobromide Trihydrate
  32. Scopolamine Hyoscine
  33. Scopolaminhydrobromid
  34. Scopolaminium Bromide
  35. Scopolammonium Bromide
  36. Scopos
  37. Sereen
  38. Skopolamin
  39. Tranaxine
  40. Transcop
  41. Transderm-Scop
  42. Transderm-V
  43. Triptone
  44. Tropic Acid, Ester with Scopine
Brand Mixtures Not Available
Chemical IUPAC Name Not Available
Chemical Formula C17H21NO4
Chemical Structure Structure
CAS Registry Number 6533-68-2
InChI Identifier InChI=1/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
InChI Key STECJAGHUSJQJN-UHFFFAOYAH
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 5184 Link Image
PubChem Substance 548858 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02229868 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Scopolamine Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 303.3529
Monoisotopic Molecular Weight 303.1471
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 6.61e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 0.8 Source: PhysProp
Predicted LogP 1.40 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -1.66 Calculated using ALOGPS
Experimental Caco2 Permeability -4.93 [ADME Research, USCD]
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric 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
Canonical SMILES CN1C2CC(CC1C1OC21)OC(=O)C(CO)C1=CC=CC=C1
Drug Category
  • Adjuvants
  • Adjuvants, Anesthesia
  • Antimuscarinics
  • Antispasmodics
  • Cholinergic Antagonists
  • Muscarinic Antagonists
  • Mydriatics
ATC Codes
AHFS Codes
  • 12:08.08
Indication For the treatment of excessive salivation, colicky abdominal pain, bradycardia, sialorrhoea, diverticulitis, irritable bowel syndrome and motion sickness.
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.
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
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms
Form Route
Disc Transdermal
Liquid Intravenous
Solution Intramuscular
Solution Intravenous
Tablet Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Muscarinic acetylcholine receptor M1
Drug Target 1 [top]
Target 1 ID 103
Target 1 Name Muscarinic acetylcholine receptor M1
Target 1 Synonyms Not Available
Target 1 Gene Name CHRM1
Target 1 Protein Sequence >Muscarinic acetylcholine receptor M1 
MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISFKVNTELKTVN
NYFLLSLACADLIIGTFSMNLYTTYLLMGHWALGTLACDLWLALDYVASNASVMNLLLIS
FDRYFSVTRPLSYRAKRTPRRAALMIGLAWLVSFVLWAPAILFWQYLVGERTVLAGQCYI
QFLSQPIITFGTAMAAFYLPVTVMCTLYWRIYRETENRARELAALQGSETPGKGGGSSSS
SERSQPGAEGSPETPPGRCCRCCRAPRLLQAYSWKEEEEEDEGSMESLTSSEGEEPGSEV
VIKMPMVDPEAQAPTKQPPRSSPNTVKRPTKKGRDRAGKGQKPRGKEQLAKRKTFSLVKE
KKAARTLSAILLAFILTWTPYNIMVLVSTFCKDCVPETLWELGYWLCYVNSTINPMCYAL
CNKAFRDTFRLLLLCRWDKRRWRKIPKRPGSVHRTPSRQC
Target 1 Number of Residues 467
Target 1 Molecular Weight 51421
Target 1 Theoretical pI 9.67
Target 1 GO Classification
Function
amine receptor activity
muscarinic acetylcholine receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in rhodopsin-like receptor activity
Target 1 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
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 25-47
  • 62-82
  • 100-121
  • 142-164
  • 187-209
  • 367-387
  • 402-421
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 34451 Link Image
Target 1 UniProtKB/Swiss-Prot ID P11229 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name ACM1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1383 bp 
ATGAACACTTCAGCCCCACCTGCTGTCAGCCCCAACATCACCGTCCTGGCACCAGGAAAG
GGTCCCTGGCAAGTGGCCTTCATTGGGATCACCACGGGCCTCCTGTCGCTAGCCACAGTG
ACAGGCAACCTGCTGGTACTCATCTCTTTCAAGGTCAACACGGAGCTCAAGACAGTCAAT
AACTACTTCCTGCTGAGCCTGGCCTGTGCTGACCTCATCATCGGTACCTTCTCCATGAAC
CTCTATACCACGTACCTGCTCATGGGCCACTGGGCTCTGGGCACGCTGGCTTGTGACCTC
TGGCTGGCCCTGGACTATGTGGCCAGCAATGCCTCCGTCATGAATCTGCTGCTCATCAGC
TTTGACCGCTACTTCTCCGTGACTCGGCCCCTGAGCTACCGTGCCAAGCGCACACCCCGC
CGGGCAGCTCTGATGATCGGCCTGGCCTGGCTGGTTTCCTTTGTGCTCTGGGCCCCAGCC
ATCCTCTTCTGGCAGTACCTGGTAGGGGAGCGGACAGTGCTAGCTGGGCAGTGCTACATC
CAGTTCCTCTCCCAGCCCATCATCACCTTTGGCACAGCCATGGCTGCCTTCTACCTCCCT
GTCACAGTCATGTGCACGCTCTACTGGCGCATCTACCGGGAGACAGAGAACCGAGCACGG
GAGCTGGCAGCCCTTCAGGGCTCCGAGACGCCAGGCAAAGGGGGTGGCAGCAGCAGCAGC
TCAGAGAGGTCTCAGCCAGGGGCTGAGGGCTCACCAGAGACTCCTCCAGGCCGCTGCTGT
CGCTGCTGCCGGGCCCCCAGGCTGCTGCAGGCCTACAGCTGGAAGGAAGAAGAGGAAGAG
GACGAAGGCTCCATGGAGTCCCTCACATCCTCAGAGGGAGAGGAGCCTGGCTCCGAAGTG
GTGATCAAGATGCCAATGGTGGACCCCGAGGCACAGGCCCCCACCAAGCAGCCCCCACGG
AGCTCCCCAAATACAGTCAAGAGGCCGACTAAGAAAGGGCGTGATCGAGCTGGCAAGGGC
CAGAAGCCCCGTGGAAAGGAGCAGCTGGCCAAGCGGAAGACCTTCTCGCTGGTCAAGGAG
AAGAAGGCGGCTCGGACCCTGAGTGCCATCCTCCTGGCCTTCATCCTCACCTGGACACCG
TACAACATCATGGTGCTGGTGTCCACCTTCTGCAAGGACTGTGTTCCCGAGACCCTGTGG
GAGCTGGGCTACTGGCTGTGCTACGTCAACAGCACCATCAACCCCATGTGCTACGCACTC
TGCAACAAAGCCTTCCGGGACACCTTTCGCCTGCTGCTGCTTTGCCGCTGGGACAAGAGA
CGCTGGCGCAAGATCCCCAAGCGCCCTGGCTCCGTGCACCGCACTCCCTCCCGCCAATGC
TGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID CHRM1 Link Image
Target 1 GenAtlas ID CHRM1 Link Image
Target 1 HGNC ID HGNC:1950 Link Image
Target 1 Chromosome Location 11
Target 1 Locus 11q13
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Arden JR, Nagata O, Shockley MS, Philip M, Lameh J, Sadee W: Mutational analysis of third cytoplasmic loop domains in G-protein coupling of the HM1 muscarinic receptor. Biochem Biophys Res Commun. 1992 Nov 16;188(3):1111-5. [PubMed Link Image]
  2. Chapman CG, Browne MJ: Isolation of the human ml (Hml) muscarinic acetylcholine receptor gene by PCR amplification. Nucleic Acids Res. 1990 Apr 25;18(8):2191. [PubMed Link Image]
  3. Peralta EG, Ashkenazi A, Winslow JW, Smith DH, Ramachandran J, Capon DJ: Distinct primary structures, ligand-binding properties and tissue-specific expression of four human muscarinic acetylcholine receptors. EMBO J. 1987 Dec 20;6(13):3923-9. [PubMed Link Image]
  4. Allard WJ, Sigal IS, Dixon RA: Sequence of the gene encoding the human M1 muscarinic acetylcholine receptor. Nucleic Acids Res. 1987 Dec 23;15(24):10604. [PubMed Link Image]
Target 1 Drug 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 Link Image]

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.