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
CHEBI:59788
CAS Number
147-20-6
UNII
33361OE3AV
DrugBank ID
DB01146
TTD ID
D0W6DY
INTEDE ID
DR2281
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 [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aminopeptidase N (ANPEP) OTP3WYFD AMPN_HUMAN Gene/Protein Processing [5]
Aryl hydrocarbon receptor (AHR) OTFE4EYE AHR_HUMAN Gene/Protein Processing [6]
Atypical chemokine receptor 2 (ACKR2) OTWYY14H ACKR2_HUMAN Gene/Protein Processing [6]
B-cell receptor-associated protein 31 (BCAP31) OTKSACR4 BAP31_HUMAN Gene/Protein Processing [6]
C-C motif chemokine 3 (CCL3) OTW2H3ND CCL3_HUMAN Gene/Protein Processing [6]
C-X-C chemokine receptor type 4 (CXCR4) OTUFSBX2 CXCR4_HUMAN Gene/Protein Processing [6]
C-X-C motif chemokine 2 (CXCL2) OTEJCYMY CXCL2_HUMAN Gene/Protein Processing [6]
Carcinoembryonic antigen-related cell adhesion molecule 6 (CEACAM6) OTQOUHVK CEAM6_HUMAN Gene/Protein Processing [6]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Gene/Protein Processing [6]
CD63 antigen (CD63) OT2UGZA9 CD63_HUMAN Gene/Protein Processing [5]
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
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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 The effects of dasatinib on IgE receptor-dependent activation and histamine release in human basophils. Blood. 2008 Mar 15;111(6):3097-107.
6 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.