Details of the Drug

General Information of Drug (ID: DMW4X37)

Drug Name
Diphenylpyraline
Synonyms
Allergen; Belfene; Dafen; Dayfen; Diafen; Difenilpiralina; Diphenylpyralamine; Diphenylpyralinum; Diphenylpyrilene; Hispril; Histryl; Histyn; Hystryl; Lergobine; Lyssipoll; Mepiben; Neargal; AN 1041; Difenilpiralina [INN-Spanish]; Diphenylpyraline (INN); Diphenylpyraline [INN:BAN]; Diphenylpyralinum [INN-Latin];Diphenylpyraline maleate (2:1); N-Methylpiperidyl-(4)-benzhydrylaether salzsauren salze; N-Methylpiperidyl-(4)-benzhydrylaether salzsauren salze [German]; 1-Methyl-4-piperidyl benzhydryl ether; 1-methyl-4-hydroxypiperidine benzhydryl ether; 4-(Benzhydryloxy)-1-methylpiperidine; 4-(Diphenylmethoxy)-1-methylpiperidine; 4-(benzhydryloxy)-N-methylpiperidine; 4-DIPHENYLMETHOXY-1-METHYLPIPERIDINE; 4-[(diphenylmethyl)oxy]-1-methylpiperidine; 4-benzhydryloxy-1-methylpiperidine
Indication
Disease Entry ICD 11 Status REF
Allergic rhinitis CA08.0 Approved [1]
Urticaria EB00-EB05 Approved [2]
Vasomotor/allergic rhinitis CA08 Approved [2]
Pruritus EC90 Investigative [2]
Therapeutic Class
Antihistamines
Affected Organisms
Humans and other mammals
ATC Code
R06AA07: Diphenylpyraline
R06AA: Aminoalkyl ethers
R06A: ANTIHISTAMINES FOR SYSTEMIC USE
R06: ANTIHISTAMINES FOR SYSTEMIC USE
R: RESPIRATORY SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 281.4
Logarithm of the Partition Coefficient (xlogp) 3.9
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Absorption
The drug is well absorbed after oral administration []
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 3.80749 micromolar/kg/day [3]
Chemical Identifiers
Formula
C19H23NO
IUPAC Name
4-benzhydryloxy-1-methylpiperidine
Canonical SMILES
CN1CCC(CC1)OC(C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3
InChIKey
OWQUZNMMYNAXSL-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3103
ChEBI ID
CHEMBL1492
CAS Number
147-20-6
UNII
33361OE3AV
DrugBank ID
DB01146
TTD ID
D0W6DY
INTEDE ID
DR2281
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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 [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Atypical chemokine receptor 2 (ACKR2) OTWYY14H ACKR2_HUMAN Gene/Protein Processing [5]
B-cell receptor-associated protein 31 (BCAP31) OTKSACR4 BAP31_HUMAN Gene/Protein Processing [5]
C-C motif chemokine 3 (CCL3) OTW2H3ND CCL3_HUMAN Gene/Protein Processing [5]
Carcinoembryonic antigen-related cell adhesion molecule 6 (CEACAM6) OTQOUHVK CEAM6_HUMAN Gene/Protein Processing [5]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Gene/Protein Processing [5]
CD63 antigen (CD63) OT2UGZA9 CD63_HUMAN Gene/Protein Processing [6]
CD81 antigen (CD81) OTQFXNAZ CD81_HUMAN Gene/Protein Processing [5]
CD82 antigen (CD82) OTH8MC64 CD82_HUMAN Gene/Protein Processing [5]
CD99 antigen (CD99) OTPUZ5DE CD99_HUMAN Gene/Protein Processing [5]
Complement C2 (C2) OTHMF4YM CO2_HUMAN Gene/Protein Processing [5]
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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
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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: 7165).
2 Diphenylpyraline FDA Label
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 Transport mechanism of an H1-antagonist at the blood-brain barrier: transport mechanism of mepyramine using the carotid injection technique. Biol Pharm Bull. 1994 May;17(5):676-9.
5 Controlled diesel exhaust and allergen coexposure modulates microRNA and gene expression in humans: Effects on inflammatory lung markers. J Allergy Clin Immunol. 2016 Dec;138(6):1690-1700. doi: 10.1016/j.jaci.2016.02.038. Epub 2016 Apr 24.
6 The effects of dasatinib on IgE receptor-dependent activation and histamine release in human basophils. Blood. 2008 Mar 15;111(6):3097-107.