Details of the Drug

General Information of Drug (ID: DMB4SFH)

Drug Name
Mepyramine
Synonyms
Anhistabs; Anhistol; Antalergan; Antallergan; Antamine; Anthisan; Copsamine; Coradon; Dipane; Dorantamin; Harvamine; Histacap; Histalon; Histapyran; Histasan; Isamin; Kriptin; Maranhist; Mepiramina; Mepiramine; Mepyramin; Mepyraminum; Mepyren; Neoantergan; Neobridal; Nyscaps; PYRA; Paraminyl; Parmal; Pyramal; Pyranisamine; Pyrilamide; Pyrilamine; Stamine; Stangen; Statomin; Thylogen; Mepyramin [German]; Pyrilamine salt with fine resin; RP 2786; [3H]mepyramine; [3H]pyrilamine; Afko-Hist; Mepiramina [INN-Spanish]; Mepyramine (INN); Mepyramine [INN:BAN]; Mepyraminum [INN-Latin]; Neo-Bridal; Wait's green mountain antihistamine; R.d. 2786; P-Methoxybenzyl-alpha-pyridyl-dimethyl-aethylendiamin; P-Methoxybenzyl-alpha-pyridyl-dimethyl-aethylendiamin [German]; P-Methoxy-benzyl-.alpha.-pyridyl-dimethyl-aethylendiamin; N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine; N-p-Methoxybenzyl-N',N'-dimethyl-N-alpha-pyridylethylenediamine; N-para-Methoxybenzyl-N',N'-dimethyl-N-alpha-pyridylethylenediamine; N-(p-Methoxybenzyl)-N',N'-dimethyl-N-2-pyridylethylenediamine; N-(para-Methoxybenzyl)-N',N'-dimethyl-N-2-pyridylethylenediamine; N',N'-Dimethyl-N-(p-methoxybenzyl)-N-(2-pyridyl)ethylenediamine; N-(p-Methoxybenzyl)-N',N'-dimethyl-N-(alpha-pyridyl)ethylenediamine; N-(p-Methoxybenzyl)-N',N'-dimethyl-N-2-(pyridylethylene)diamine; N-Dimethylamino-aethyl-N-p-methoxy-benzyl-.alpha.-amino-pyridin-maleat; N-(p-Methoxybenzyl)-N',N'-dimethyl-N-(alpha.-pyridyl)ethylenediamine; N-(p-Methoxybenzyl)-N',N'-dimethyl-N-2-pyridyl-1,2-ethanediamine; N-[(4-methoxyphenyl)methyl]-N',N'-dimethyl-N-2-pyridinyl-1,2-ethanediamine; N-((4-Methoxyphenyl)methyl)-N',N'-dimethyl-N-2-pyridinyl-1,2-ethanediamine; N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine; N,N-dimethyl-N'-{[4-(methyloxy)phenyl]methyl}-N'-pyridin-2-ylethane-1,2-diamine; 2-((2-(Dimethylamino)ethyl)-(p-methoxybenzyl)amino)pyridine; 2-((p-Methoxybenzyl)(2-(dimethylamino)ethyl)amino)pyridine; 2-[(p-Methoxybenzyl)[2-(dimethylamino)ethyl]amino]pyridine; 2-[[2-(Dimethylamino)ethyl](p-methoxybenzyl)amino]pyridine; 2-[[2-(Dimethylamino)ethyl]-(p-methoxybenzyl)amino]pyridine; 2-dimethylaminoethyl-p-anisyl-(2-pyridyl)amine
Indication
Disease Entry ICD 11 Status REF
Allergic rhinitis CA08.0 Approved [1]
Allergy 4A80-4A85 Approved [2]
Common cold CA00 Approved [3]
Dysmenorrhea GA34.3 Approved [4]
Seasonal allergic rhinitis CA08.01 Approved [1]
Urticaria EB00-EB05 Approved [5]
Vasomotor/allergic rhinitis CA08 Approved [6]
Pruritus EC90 Investigative [7]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Antiasthmatic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 285.4
Logarithm of the Partition Coefficient (xlogp) 3.3
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C17H23N3O
IUPAC Name
N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine
Canonical SMILES
CN(C)CCN(CC1=CC=C(C=C1)OC)C2=CC=CC=N2
InChI
InChI=1S/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3
InChIKey
YECBIJXISLIIDS-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4992
ChEBI ID
CHEBI:6762
CAS Number
91-84-9
DrugBank ID
DB06691
TTD ID
D08JZS
VARIDT ID
DR00564
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Histamine H1 receptor (H1R) TTTIBOJ HRH1_HUMAN Antagonist [8]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation/carnitine transporter 2 (SLC22A5) DT3HUVD S22A5_HUMAN Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cholinesterase (BCHE) OTOH3WQ9 CHLE_HUMAN Gene/Protein Processing [10]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Protein Interaction/Cellular Processes [11]
Kininogen-1 (KNG1) OT4X9LDE KNG1_HUMAN Gene/Protein Processing [12]
Potassium voltage-gated channel subfamily H member 2 (KCNH2) OTZX881H KCNH2_HUMAN Gene/Protein Processing [13]
Sodium-dependent serotonin transporter (SLC6A4) OT6FGDLW SC6A4_HUMAN Protein Interaction/Cellular Processes [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Allergic rhinitis
ICD Disease Classification CA08.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Histamine H1 receptor (H1R) DTT HRH1 6.74E-01 0.13 0.43
Organic cation/carnitine transporter 2 (SLC22A5) DTP OCTN2 9.94E-01 1.54E-02 6.61E-02
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 Same Disease as Mepyramine
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Phenyltoloxamine DMKAEQW Moderate Additive anticholinergic effects by the combination of Mepyramine and Phenyltoloxamine. Allergic/hypersensitivity disorder [4A80-4A8Z] [15]
Coadministration of a Drug Treating the Disease Different from Mepyramine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Umeclidinium DM4E8O9 Moderate Additive anticholinergic effects by the combination of Mepyramine and Umeclidinium. Chronic obstructive pulmonary disease [CA22] [16]
Revefenacin DMMP5SI Moderate Additive anticholinergic effects by the combination of Mepyramine and Revefenacin. Chronic obstructive pulmonary disease [CA22] [16]
OPC-34712 DMHG57U Moderate Additive anticholinergic effects by the combination of Mepyramine and OPC-34712. Depression [6A70-6A7Z] [15]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Mepyramine and Esketamine. Depression [6A70-6A7Z] [17]
Belladonna DM2RBWK Moderate Additive anticholinergic effects by the combination of Mepyramine and Belladonna. Infectious gastroenteritis/colitis [1A40] [15]
Allopregnanolone DMNLHAC Moderate Additive CNS depression effects by the combination of Mepyramine and Allopregnanolone. Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z] [18]
Lasmiditan DMXLVDT Moderate Additive CNS depression effects by the combination of Mepyramine and Lasmiditan. Migraine [8A80] [17]
Methylscopolamine DM5VWOB Moderate Additive anticholinergic effects by the combination of Mepyramine and Methylscopolamine. Peptic ulcer [DA61] [15]
Acrivastine DMTIGA0 Moderate Additive anticholinergic effects by the combination of Mepyramine and Acrivastine. Vasomotor/allergic rhinitis [CA08] [15]
⏷ Show the Full List of 9 DDI Information of This Drug

References

1 Antiallergic anti-inflammatory effects of H1-antihistamines in humans. Clin Allergy Immunol. 2002;17:101-39.
2 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: 1220).
3 Determination of amine ingredients in cough-cold liquids by reversed-phase ion-pair high-performance liquid chromatography. J Pharm Sci. 1982 Oct;71(10):1108-12.
4 Naproxen, paracetamol and pamabrom versus paracetamol, pyrilamine and pamabrom in primary dysmenorrhea: a randomized, double-blind clinical trial. Medwave. 2016 Oct 24;16(9):e6587.
5 The widely used antihistamine mepyramine causes topical pain relief through direct blockade of nociceptor sodium channels. FASEB J. 2021 Dec;35(12):e22025.
6 A standard database for drug repositioning. Sci Data. 2017 Mar 14;4:170029.
7 Pharmacology of sinomenine, an anti-rheumatic alkaloid from Sinomenium acutum. Acta Med Okayama. 1976 Feb;30(1):1-20.
8 Antinociception induced by central administration of histamine in the formalin test in rats. Indian J Physiol Pharmacol. 2008 Jul-Sep;52(3):249-54.
9 Genetic deficiency of carnitine/organic cation transporter 2 (slc22a5) is associated with altered tissue distribution of its substrate pyrilamine in mice. Biopharm Drug Dispos. 2009 Dec;30(9):495-507.
10 Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity. Toxicol Appl Pharmacol. 1975 Feb;31(2):179-90.
11 A role for endogenous histamine in interleukin-8-induced neutrophil infiltration into mouse air-pouch: investigation of the modulatory action of systemic and local dexamethasone. Br J Pharmacol. 1994 Jul;112(3):801-8. doi: 10.1111/j.1476-5381.1994.tb13150.x.
12 Effects of capsaicin, bradykinin and prostaglandin E2 in the human skin. Br J Dermatol. 1992 Feb;126(2):111-7. doi: 10.1111/j.1365-2133.1992.tb07806.x.
13 Comparative evaluation of HERG currents and QT intervals following challenge with suspected torsadogenic and nontorsadogenic drugs. J Pharmacol Exp Ther. 2006 Mar;316(3):1098-106. doi: 10.1124/jpet.105.093393. Epub 2005 Nov 8.
14 GBR compounds and mepyramines as cocaine abuse therapeutics: chemometric studies on selectivity using grid independent descriptors (GRIND). J Med Chem. 2002 Apr 11;45(8):1577-84. doi: 10.1021/jm011007+.
15 Kulik AV, Wilbur R "Delirium and stereotypy from anticholinergic antiparkinson drugs." Prog Neuropsychopharmacol Biol Psychiatry 6 (1982): 75-82. [PMID: 7202232]
16 Product Information. Anoro Ellipta (umeclidinium-vilanterol). GlaxoSmithKline, Research Triangle Park, NC.
17 Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002]
18 Gilman AG, Rall TW, Nies AS, Taylor P, eds. "Goodman and Gilman's the Pharmacological Basis of Therapeutics. 8th ed." New York, NY: Pergamon Press Inc. (1990):.