Diphenylpyraline

Summary

Diphenylpyraline (CHEMBL1492) is an approved small-molecule H1-receptor antagonist (ATC R06AA07); indicated across 1 condition including allergic disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: R06AA07 (+1 more)
• Indications: 1 condition
• Chemistry: 281.4 Da · C19H23NO

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1492
Name	Diphenylpyraline
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	3103
ChEBI	CHEBI:59788
ATC	R06AA07, R06AA57
Molecular formula	C19H23NO
Molecular weight	281.4
InChIKey	OWQUZNMMYNAXSL-UHFFFAOYSA-N

SMILES: CN1CCC(CC1)OC(C2=CC=CC=C2)C3=CC=CC=C3

IUPAC name: 4-benzhydryloxy-1-methylpiperidine

ChEBI definition: A member of the class of piperidines that is the benzhydryl ether derivative of 1-methyl-4-hydroxypiperidine. A sedating antihistamine, it is used as the hydrochloride for the symptomatic relief of allergic conditions including rhinitis and hay fever, and in pruritic skin disorders. It is also used as the teoclate salt (piprinhydrinate) as an ingredient in compound preparations for the symptomatic relief of coughs and the common cold.

Pharmacological roles (ChEBI): H1-receptor antagonist, cholinergic antagonist.

Also known as: Difenilpiralina, Diphenylpyraline, SID11112289, SID50123603, SID50123604, DIPHENYLPYRALINE, DIPHENYLPYRALINE HYDROCHLORIDE, diphenylpyraline

Parent form; salt/anhydrous children: CHEMBL1564

Patent coverage: 1,281 distinct patent families (4,858 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 15 (assay-derived). Sample: 4’-phosphopantetheinyl transferase ffp, Alpha-2A adrenergic receptor, D(1A) dopamine receptor, Muscarinic acetylcholine receptor M2, 5-hydroxytryptamine receptor 1A, Muscarinic acetylcholine receptor M1, Sodium-dependent noradrenaline transporter, Alpha-1A adrenergic receptor, Mu-type opioid receptor, D(3) dopamine receptor, Sodium-dependent dopamine transporter, Voltage-gated inwardly rectifying potassium channel KCNH2, Histamine H3 receptor, Cytochrome P450 2D6, Sodium-dependent dopamine transporter.

Bioactivity

ChEMBL activities: 12 potent at pChembl ≥ 5 of 16 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
CHRM1	7.01	AC50	97.9	nM	CHEMBL_ACT_25210089
CHRM2	6.76	AC50	172.7	nM	CHEMBL_ACT_25195592
P23977	6.38	IC50	420	nM	CHEMBL_ACT_1616577
SLC6A3	6.36	AC50	437.4	nM	CHEMBL_ACT_25124815
DRD3	6.14	AC50	723.2	nM	CHEMBL_ACT_25194382
SLC6A2	5.72	AC50	1907	nM	CHEMBL_ACT_25145856
OPRM1	5.24	AC50	5710	nM	CHEMBL_ACT_25158031
CYP2D6	5.2	Potency	6310	nM	CHEMBL_ACT_4965800
CYP2D6	5.2	AC50	6310	nM	CHEMBL_ACT_5987608
ADRA2A	5.13	AC50	7402	nM	CHEMBL_ACT_25156285
DRD1	5.12	AC50	7578	nM	CHEMBL_ACT_25115066
KCNH2	5.06	AC50	8800	nM	CHEMBL_ACT_25117379

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
allergic disease	4	MONDO:0005271	MONDO:0005271

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).