Drug Details

General Information of the Drug (ID: DR0456)
Name
Scopolamine
Synonyms
scopolamine; Hyoscine; (-)-Hyoscine; 51-34-3; Scopine (-)-tropate; l-Scopolamine; Scopine tropate; 6,7-Epoxytropine tropate; Transderm-Scop; (-)-Scopolamine; Hyosol; Atrochin; Atroquin; Isopto Hyoscine; Epoxytropine tropate; Scopolamine hydrobromide; 6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropate; UNII-DL48G20X8X; Beldavrin; Scopamin; CHEMBL3084722; alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester; Skopolamin; Hyosceine; Scop; DL48G20X8X; Tropic acid, ester with scopine; CHEBI:16794; LSM-4015; Isoscopil; Tranaxine; (1S,3S,5R,6R,7S)-6,7-epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoate; Hysco; Hyoscine bromide; Scopace; Transderm scop; Scopolamine HCl; Boro-Scopol; Scopolaminium bromide; 1alphaH,5alphaH-Tropan-3alpha-ol, 6beta,7beta-epoxy-, (-)-tropate (ester); Scopolammonium bromide; l-Hyoscine hydrobromide; (1R,2R,4S,5S,7s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl (S)-3-hydroxy-2-phenylpropanoate; SEE; (-)-Scopolamine bromide; l-Scopolamine-hydrobromide; SCOPOLAMINE BROMIDE; (-)-Hyoscine hydrobromide; Scopoderm; (+)-Scopolamine; levo-duboisine; (+)-Hyoscine; (1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate; [(1R,2R,4S,5S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoate; Hyoscyine hydrobromide; Atroscine Hydrobromide; Hydroscine hydrobromide; hydrobromicum, Scopolaminum; Tropane alkaloid; HSDB 4074; EINECS 200-090-3; NSC61806; S-(-)-Tropate; Prestwick3_000877; EC 200-090-3; 6beta,7beta-Epoxy-3alpha-tropanyl S-(-)-tropate; SCHEMBL16226; BSPBio_000953; GTPL330; 6beta,7beta-Epoxy-1alpha,5alpha-tropan-3alpha-ol; BPBio1_001049; CHEMBL569713; CHEMBL1906925; DTXSID6023573; SCHEMBL22393238; CHEBI:93572; HMS2090N13; HMS3886L22; HY-N0296; AC-968; BDBM50263508; CS0019; s9326; ZINC13118910; AKOS025402477; Tropic acid, 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(sup 2,4))non-7-yl ester; ZINC100037020; ZINC101147375; CCG-267504; CS-6609; DB00747; 3-Oxa-9-azatricyclo(3.3.1.0(sup 2,4))nonan-7-ol, 9-methyl-, tropate (ester); 3-Oxa-9-azatricyclo(3.3.1.O(sup 2,4))nonan-7-ol, 9-methyl-, tropate (ester); SMP1_000270; NCGC00024357-04; NCGC00024357-05; (1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate; AB00429689; AB00429689-30; AB00429689-31; AB00429689_32; Q337188; (methyl[?]yl) (2S)-3-hydroxy-2-phenyl-propanoate; BRD-K89923877-003-02-4; Q27165268; (1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate; (1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl (2R)-3-hydroxy-2-phenylpropanoate; (1R,2R,4S,5S,7s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate; [7(S)-(1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)]-.alpha.-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo-[3.3.1.0^2,4]non-7-yl ester; Benzeneacetic acid, alpha-(hydroxymethyl)-, (1alpha,2beta,4beta,5alpha,7beta)-9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (alphaS)-; Benzeneacetic acid, alpha-(hydroxymethyl)-, 9-methyl-3-oxa-9-azatricyclo(3.3.1.02,4)non-7-yl ester, (7(S)-(1alpha,2beta,4beta,5alpha,7beta))-
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Molecular Type
Small molecule
Disease Addictive disorder [ICD-11: 6C50-6C5Z] Approved [1]
Depression [ICD-11: 6A70-6A71] Investigative
Structure
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2D MOL

3D MOL

ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 50.8 +/- 1.76 mcgmin/L
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 0.54 +/- 0.1 mcg/L
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 23.5 +/- 8.2 min
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Bioavailability
The bioavailability of drug is 13 +/- 1%
Clearance
The clearance of drug is 81.2 +/- 1.55 L/h
Elimination
Following oral administration, approximately 2.6% of unchanged scopolamine is recovered in urine
Half-life
The concentration or amount of drug in body reduced by one-half in 68.7 +/- 1.0 minutes (intravenous), 63.7 +/- 1.3 minutes (oral), and 69.1 +/- 8.0 minutes (intramuscular administration)
Metabolism
The drug is metabolized via the liver
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.00109 micromolar/kg/day
Vd
The volume of distribution (Vd) of drug is 141.3 +/- 1.6 L
Water Solubility
The ability of drug to dissolve in water is measured as 666.67 mg/mL
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C17H21NO4
PubChem CID
3000322
Canonical SMILES
CN1C2CC(CC1C3C2O3)OC(=O)C(CO)C4=CC=CC=C4
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
InChIKey
STECJAGHUSJQJN-USLFZFAMSA-N
CAS Number
CAS 114-49-8
ChEBI ID
CHEBI:16794
TTD Drug ID
D0B7YT
DrugBank ID
DB00747
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Decrease the Adverse Effect of This Drug
          Acteoside      Cistanche     Click to Show/Hide the Molecular Data of This NP
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Male ICR mice, weighing 25-30 g, were used for passive avoidance and water maze tests.
                    Experimental
                    Result(s)		 Acteoside of Callicarpa dichotoma attenuates scopolamine-induced memory impairments.
Target and Pathway
Target(s) Muscarinic acetylcholine receptor M2 (CHRM2)  Molecule Info  [3]
KEGG Pathway Calcium signaling pathway Click to Show/Hide
2 cAMP signaling pathway
3 Neuroactive ligand-receptor interaction
4 PI3K-Akt signaling pathway
5 Cholinergic synapse
6 Regulation of actin cytoskeleton
Panther Pathway Alzheimer disease-amyloid secretase pathway Click to Show/Hide
2 Heterotrimeric G-protein signaling pathway-Gi alpha and Gs alpha mediated pathway
3 Heterotrimeric G-protein signaling pathway-Gq alpha and Go alpha mediated pathway
4 Muscarinic acetylcholine receptor 2 and 4 signaling pathway
Pathwhiz Pathway Muscle/Heart Contraction Click to Show/Hide
Reactome Muscarinic acetylcholine receptors Click to Show/Hide
2 G alpha (i) signalling events
WikiPathways SIDS Susceptibility Pathways Click to Show/Hide
2 Monoamine GPCRs
3 Calcium Regulation in the Cardiac Cell
4 Regulation of Actin Cytoskeleton
5 GPCRs, Class A Rhodopsin-like
6 GPCR ligand binding
7 GPCR downstream signaling
8 GPCRs, Other
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 330).
Reference 2 Acteoside of Callicarpa dichotoma attenuates scopolamine-induced memory impairments. Biol Pharm Bull. 2006 Jan;29(1):71-4.
Reference 3 The amygdala modulates morphine-induced state-dependent memory retrieval via muscarinic acetylcholine receptors. Neuroscience. 2009 May 5;160(2):255-63.
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