Molecule Details
InChIKeyZZVUWRFHKOJYTH-UHFFFAOYSA-N
Compound NameDiphenhydramine
Canonical SMILESCN(C)CCOC(c1ccccc1)c1ccccc1
Clinical Status Clinical Multi-Target
Targets (Human+Pathogen)11
Pfam Stratification Cross-Family
Avg pChEMBL6.74
SourceChEMBL;BindingDB;TTD_MultiTarget
2D Structure
2D structure
Activity Profile
DrugBank Annotations
DrugBank ID DB01075
Drug NameDiphenhydramine
CAS Number58-73-1
Groups approved investigational
ATC Codes D04AA32 R06AA02 M01AE57 D04AA33 R06AA52
DescriptionDiphenhydramine - perhaps known most commonly as its brand name formulation Benadryl - is a first-generation H1 receptor antihistamine that is used extensively for the treatment of seasonal allergies, insect bites and stings, and rashes [L5263, L5266, L5269, F3379]. However, it also has antiemetic, ...
Categories: Agents producing tachycardia Amines Aminoalkyl Ethers Anesthetics Anesthetics, Local Anti-Allergic Agents Anticholinergic Agents Antiemetics Antihistamines for Systemic Use Antihistamines for Topical Use Antiinflammatory and Antirheumatic Products Antiinflammatory and Antirheumatic Products, Non-Steroids Antipruritics, Incl. Antihistamines, Anesthetics, Etc. Benzene Derivatives Benzhydryl Compounds Central Nervous System Agents Central Nervous System Depressants Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Dermatologicals Drugs causing inadvertant photosensitivity Ethanolamine Derivatives Ethylamines First Generation Antihistamines Gastrointestinal Agents Histamine Agents Histamine Antagonists Histamine H1 Antagonists Hypnotics and Sedatives Muscarinic Antagonists Musculo-Skeletal System OCT2 Inhibitors Photosensitizing Agents Potential QTc-Prolonging Agents Propionates QTc Prolonging Agents Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome Sleep Aids, Pharmaceutical
Cross-references: BindingDB: 50017674 ChEBI: 4636 CHEMBL657 ChemSpider: 2989 Drugs Product Database (DPD): 182 Guide to Pharmacology: 1224 IUPHAR: 1224 C06960 D00300 PDB: 2PM PharmGKB: PA449349 PubChem:3100 PubChem:46505484 RxCUI: 3498 Therapeutic Targets Database: DAP000490 Wikipedia: Diphenhydramine ZINC: ZINC000000020244
Target Activities (11)
Target Gene Organism Category Pfam pChEMBL Type Source
P35367 HRH1 Homo sapiens Human PF00001 7.8 Ki ChEMBL;BindingDB
P35348 ADRA1A Homo sapiens Human PF00001 7.4 pIC50 TTD_MultiTarget
P11229 CHRM1 Homo sapiens Human PF00001 7.0 Ki ChEMBL;BindingDB
P08173 CHRM4 Homo sapiens Human PF00001 7.0 Ki ChEMBL;BindingDB
P08912 CHRM5 Homo sapiens Human PF00001 6.6 Ki ChEMBL;BindingDB
P20309 CHRM3 Homo sapiens Human PF00001 6.6 Ki ChEMBL;BindingDB
P08172 CHRM2 Homo sapiens Human PF00001 6.6 Ki ChEMBL;BindingDB
P28223 HTR2A Homo sapiens Human PF00001 6.4 Ki ChEMBL
Q99720 SIGMAR1 Homo sapiens Human PF04622 6.3 Ki ChEMBL
P28335 HTR2C Homo sapiens Human PF00001 6.2 IC50 ChEMBL
P41595 HTR2B Homo sapiens Human PF00001 6.2 Ki ChEMBL
DrugBank Target Actions (10)
Target Gene Target Name Action Type
P10635 CYP2D6 Cytochrome P450 2D6 inhibitor enzymes
P10635 CYP2D6 Cytochrome P450 2D6 substrate enzymes
P11712 CYP2C9 Cytochrome P450 2C9 substrate enzymes
P23219 PTGS1 Prostaglandin G/H synthase 1 substrate enzymes
P33261 CYP2C19 Cytochrome P450 2C19 substrate enzymes
P08172 CHRM2 Muscarinic acetylcholine receptor M2 antagonist targets
P50135 P50135 Histamine N-methyltransferase inhibitor targets
P35367 HRH1 Histamine H1 receptor inverse agonist targets
O15244 SLC22A2 Solute carrier family 22 member 2 inhibitor transporters
O76082 O76082 Organic cation/carnitine transporter 2 inhibitor transporters