Details of the Drug

General Information of Drug (ID: DM5VWOB)

Drug Name
Methylscopolamine
Synonyms
Methscopolamine; methscopolamine; N-Methylscopolamine; N-methyl scopolamine; UNII-VDR09VTQ8U; VDR09VTQ8U; 13265-10-6; CHEMBL376897; (1r,2r,4s,5s)-7-{[(2s)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclo[33102,4]nonane; Metylskopolamin; 56552-70-6; 3-Oxa-9-azoniatricyclo[33102,4]nonane, 7-[(2S)-3-hydroxy-1-oxo-2-phenylpropoxy]-9,9-dimethyl-, (1a,2b,4b,5a,7b); HSDB 5420; [3H]N-methylscopolamine; [3H]N-methyl scopolamine; [3H]NMS; Methyl scopolamine; 3C0
Indication
Disease Entry ICD 11 Status REF
Peptic ulcer DA61 Approved [1], [2], [3]
Therapeutic Class
Anticholinergic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 318.4
Topological Polar Surface Area (xlogp) 1.3
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C18H24NO4+
IUPAC Name
[(1S,2S,4R,5R)-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoate
Canonical SMILES
C[N+]1([C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)[C@H](CO)C4=CC=CC=C4)C
InChI
InChI=1S/C18H24NO4/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11/h3-7,12-17,20H,8-10H2,1-2H3/q+1/t12?,13-,14-,15+,16-,17+/m1/s1
InChIKey
LZCOQTDXKCNBEE-XJMZPCNVSA-N
Cross-matching ID
PubChem CID
71183
ChEBI ID
CHEBI:135361
CAS Number
13265-10-6
DrugBank ID
DB11315
TTD ID
D0M6VK

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Muscarinic acetylcholine receptor (CHRM) TTOXS3C NOUNIPROTAC Antagonist [4]
Muscarinic acetylcholine receptor M2 (CHRM2) TTYEG6Q ACM2_HUMAN Antagonist [5]
Muscarinic acetylcholine receptor M3 (CHRM3) TTQ13Z5 ACM3_HUMAN Antagonist [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Peptic ulcer
ICD Disease Classification DA61
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Muscarinic acetylcholine receptor M2 (CHRM2) DTT CHRM2 4.61E-07 -0.59 -0.73
Muscarinic acetylcholine receptor M3 (CHRM3) DTT CHRM3 4.61E-07 -0.59 -0.73
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Methylscopolamine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Oliceridine DM6MDCF Moderate Additive antimotility effects by the combination of Methylscopolamine and Oliceridine. Acute pain [MG31] [35]
Revefenacin DMMP5SI Moderate Additive anticholinergic effects by the combination of Methylscopolamine and Revefenacin. Chronic obstructive pulmonary disease [CA22] [36]
Belladonna DM2RBWK Moderate Additive anticholinergic effects by the combination of Methylscopolamine and Belladonna. Infectious gastroenteritis/colitis [1A40] [37]

References

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: 316).
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 Drug information of Methylscopolamine, 2008. eduDrugs.
4 Lithocholylcholine, a bile acid/acetylcholine hybrid, is a muscarinic receptor antagonist. J Pharmacol Exp Ther. 2002 Oct;303(1):29-35.
5 Methylacridinium and its cholinergic properties. Neurotox Res. 2009 Nov;16(4):372-7.
6 Interaction of neuromuscular blocking drugs with recombinant human m1-m5 muscarinic receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1998 Nov;125(5):1088-94.
7 Thiochrome enhances acetylcholine affinity at muscarinic M4 receptors: receptor subtype selectivity via cooperativity rather than affinity. Mol Pharmacol. 2004 Jan;65(1):257-66.
8 Pharmacological characterization of GSK573719 (umeclidinium): a novel, long-acting, inhaled antagonist of the muscarinic cholinergic receptors for treatment of pulmonary diseases. J Pharmacol Exp Ther. 2013 May;345(2):260-70.
9 Characterisation of [3H]-darifenacin as a novel radioligand for the study of muscarinic M3 receptors. J Recept Signal Transduct Res. 1997 Jan-May;17(1-3):177-84.
10 Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line. J Pharmacol Exp Ther. 1998 Feb;284(2):500-7.
11 Effects of propiverine hydrochloride (propiverine) on the muscarinic receptor binding affinity in guinea pig tissues and on salivation in conscious dogs. Nihon Yakurigaku Zasshi. 1999 Mar;113(3):157-66.
12 Clinical pipeline report, company report or official report of GlaxoSmithKline.
13 2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
14 The amygdala modulates morphine-induced state-dependent memory retrieval via muscarinic acetylcholine receptors. Neuroscience. 2009 May 5;160(2):255-63.
15 Competitive and non-competitive antagonism exhibited by 'selective' antagonists at atrial and ileal muscarinic receptor subtypes. Br J Pharmacol. 1987 Apr;90(4):701-7.
16 Long-acting bronchodilators in COPD: Where are we now and where are we going Breathe 06/2014; 10(2):110-120.
17 Design, synthesis, and neurochemical evaluation of 5-(3-alkyl-1,2,4- oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidines as M1 muscarinic receptor agonists. J Med Chem. 1993 Apr 2;36(7):842-7.
18 6beta-Acetoxynortropane: a potent muscarinic agonist with apparent selectivity toward M2-receptors. J Med Chem. 1998 Jun 4;41(12):2047-55.
19 Demonstration of bladder selective muscarinic receptor binding by intravesical oxybutynin to treat overactive bladder. J Urol. 2004 Nov;172(5 Pt 1):2059-64.
20 Cholinergic regulation of the corpora allata in adult male loreyi leafworm Mythimna loreyi. Arch Insect Biochem Physiol. 2002 Apr;49(4):215-24.
21 Clinical pipeline report, company report or official report of FemmePharma.
22 Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41.
23 Beneficial effect of muscarinic-2 antagonist on dilated cardiomyopathy induced by autoimmune mechanism against muscarinic-2 receptor. J Cardiovasc Pharmacol. 2001 Oct;38 Suppl 1:S43-9.
24 Improving the oral efficacy of CNS drug candidates: discovery of highly orally efficacious piperidinyl piperidine M2 muscarinic receptor antagonists. J Med Chem. 2002 Dec 5;45(25):5415-8.
25 In vivo muscarinic cholinergic mediated effects of Lu 25-109, a M1 agonist and M2/M3 antagonist in vitro. Psychopharmacology (Berl). 1998 Jun;137(3):233-40.
26 Himbacine analogs as muscarinic receptor antagonists--effects of tether and heterocyclic variations. Bioorg Med Chem Lett. 2004 Aug 2;14(15):3967-70.
27 Signal transduction underlying carbachol-induced contraction of human urinary bladder. J Pharmacol Exp Ther. 2004 Jun;309(3):1148-53.
28 DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6.
29 Role of parasympathetic nerves and muscarinic receptors in allergy and asthma.Chem Immunol Allergy.2012;98:48-69.
30 M(1) and M(3) muscarinic receptors are involved in the release of urinary bladder-derived relaxant factor. Pharmacol Res. 2009 May;59(5):300-5.
31 Muscarinic M3-receptors mediate cholinergic synergism of mitogenesis in airway smooth muscle. Am J Respir Cell Mol Biol. 2003 Feb;28(2):257-62.
32 Comparison of muscarinic receptor selectivity of solifenacin and oxybutynin in the bladder and submandibular gland of muscarinic receptor knockout ... Eur J Pharmacol. 2009 Aug 1;615(1-3):201-6.
33 Degradation of submandibular gland AQP5 by parasympathetic denervation of chorda tympani and its recovery by cevimeline, an M3 muscarinic receptor ... Am J Physiol Gastrointest Liver Physiol. 2008 Jul;295(1):G112-G123.
34 Agonist-regulated alteration of the affinity of pancreatic muscarinic cholinergic receptors. J Biol Chem. 1993 Oct 25;268(30):22436-43.
35 Product Information. Apadaz (acetaminophen-benzhydrocodone). KemPharm, Inc, Coralville, IA.
36 Cole JM, Sheehan AH, Jordan JK "Concomitant use of ipratropium and tiotropium in chronic obstructive plmonary disease." Ann Pharmacother 46 (2012): 1717-21. [PMID: 23170031]
37 Cohen MA, Alfonso CA, Mosquera M. Development of urinary retention during treatment with clozapine and meclizine [published correction appears in Am J Psychiatry 1994 Jun;151(6):952]. Am J Psychiatry. 1994;151(4):619-620. [PMID: 8147469]