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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL657
CHEMBL657
Compound Name DIPHENHYDRAMINE
ChEMBL Synonyms Hydramine | Alledryl | Dibenil | DIPHENHYDRAMINE CITRATE | DREEMON | COLTEX | BENADRYL PRESERVATIVE FREE | NYTOL | MEDINEX | HYDRAMINE | HISTERGAN | DIPHENHYDRAMINE LAURYLSULFATE | Diphenhydramine | FEDRIL | DIBENIL | BELDIN | DIPHENHYDRAMINE TANNATE | Diphen | VICKS FORMULA 44 | TIXYLIX CATARRH | GPPE ORAL SOLN | DIPHENHYDRAMINE HYDROCHLORIDE PRESERVATIVE FREE | DIPHENHYDRAMINE HYDROCHLORIDE | DIPHEN | CALADRYL | Silphen | Benadryl | Antitussive | DIPHENHYDRAMINE | Syntedril | SLEEPIA | Dytuss | BENYLIN | BELIX | ANTITUSSIVE | Beldin | SILPHEN | BENADRYL | Benylin | Belix | PAXIDORM | NYTOL ONE-A-NIGHT | NIGHTCALM | GPPE COUGH EXPECT PAED | DIMEDROL
Max Phase 4 (Approved)
Trade Names ANTITUSSIVE | BELIX | BENYLIN | Dytuss | SLEEPIA | Syntedril | BENADRYL | SILPHEN | Alledryl | GPPE COUGH EXPECT PAED | NIGHTCALM | NYTOL ONE-A-NIGHT | PAXIDORM | CALADRYL | DIPHEN | DIPHENHYDRAMINE HYDROCHLORIDE | DIPHENHYDRAMINE HYDROCHLORIDE PRESERVATIVE FREE | GPPE ORAL SOLN | TIXYLIX CATARRH | VICKS FORMULA 44 | BENADRYL PRESERVATIVE FREE | COLTEX | DREEMON | HISTERGAN | HYDRAMINE | MEDINEX | NYTOL | BELDIN | DIBENIL | FEDRIL
Molecular Formula C17H21NO

Additional synonyms for CHEMBL657 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN(C)CCOC(c1ccccc1)c2ccccc2
Standard InChI InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11 ...
Download InChI
Standard InChI Key ZZVUWRFHKOJYTH-UHFFFAOYSA-N

Sources

  • BindingDB Database
  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL657

Molecule Features

CHEMBL657 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:N Availability Type:Over-The-Counter

Mechanism of Action

Mechanism of Action ChEMBL Target References
Histamine H1 receptor antagonist Histamine H1 receptor PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma2ClinicalTrials
Cocaine-Related DisordersD019970EFO:0002610cocaine dependence2ClinicalTrials
DementiaD003704HP:0000726dementia3ClinicalTrials
Endometrial NeoplasmsD016889EFO:0004230endometrial neoplasm2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
PruritusD011537HP:0000989Pruritus4ATC
StomatitisD013280EFO:1001904oral mucositis3ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
AlcoholismD000437EFO:0003829alcohol dependence2ClinicalTrials
InflammationD007249MP:0001845inflammation3ClinicalTrials
LymphomaD008223EFO:0000574lymphoma2ClinicalTrials
StomatitisD0132803ClinicalTrials
UrticariaD014581EFO:0005531urticaria3ClinicalTrials
NauseaD009325HP:0002018Nausea2ClinicalTrials
Leukemia, Mast-CellD007946EFO:0007359mast-cell leukemia2ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells2ClinicalTrials
Rhinitis, Allergic, SeasonalD006255EFO:0005854allergic rhinitis1ClinicalTrials
Glycogen Storage Disease Type IID006009Orphanet:365Glycogen storage disease due to acid maltase deficiency1ClinicalTrials
Hepatitis B, ChronicD019694EFO:0004239chronic hepatitis B infection2ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
HypersensitivityD006967EFO:0003785allergy1ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression3ClinicalTrials
FibrosisD005355EFO:0006890fibrosis1ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
Stomatitis, AphthousD013281EFO:0003938aphthous ulcer2ClinicalTrials
ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma2ClinicalTrials
Diabetic NeuropathiesD003929EFO:1000783diabetic neuropathy2ClinicalTrials
Hypotension, OrthostaticD007024EFO:0005252orthostatic hypotension1ClinicalTrials
AnxietyD001007EFO:0005230anxiety3ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma2ClinicalTrials
CoughD003371HP:0012735Cough3ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma1ClinicalTrials
Lupus Erythematosus, SystemicD008180EFO:0002690systemic lupus erythematosus3ClinicalTrials
Lupus NephritisD008181EFO:0005761lupus nephritis3ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm2ClinicalTrials
PainD010146EFO:0003843pain3ClinicalTrials
ClinicalTrials
Restless Legs SyndromeD012148EFO:0004270restless legs syndrome2ClinicalTrials
Migraine DisordersD008881EFO:0003821migraine disorder3ClinicalTrials
ClinicalTrials
NeoplasmsD009369EFO:0000311cancer2ClinicalTrials
RhinitisD0122203ClinicalTrials
HeadacheD006261HP:0002315Headache3ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer1ClinicalTrials
VomitingD0148392ClinicalTrials
Graft vs Host DiseaseD006086EFO:0004599acute graft vs. host disease2ClinicalTrials
Kidney DiseasesD007674EFO:0003086kidney disease1ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma3ClinicalTrials
MelanomaD008545EFO:0000756melanoma1ClinicalTrials

Clinical Data

ClinicalTrials.gov DIPHENHYDRAMINE
The Cochrane Collaboration DIPHENHYDRAMINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL657. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL338 Dopamine transporter Rattus norvegicus 1.000
CHEMBL313 Serotonin transporter Rattus norvegicus 1.000
CHEMBL228 Serotonin transporter Homo sapiens 1.000
CHEMBL238 Dopamine transporter Homo sapiens 1.000
CHEMBL222 Norepinephrine transporter Homo sapiens 1.000
CHEMBL276 Muscarinic acetylcholine receptor M1 Rattus norvegicus 1.000
CHEMBL231 Histamine H1 receptor Homo sapiens 1.000
CHEMBL2035 Muscarinic acetylcholine receptor M5 Homo sapiens 0.996
CHEMBL287 Sigma opioid receptor Homo sapiens 0.993
CHEMBL1821 Muscarinic acetylcholine receptor M4 Homo sapiens 0.982
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.975
CHEMBL309 Muscarinic acetylcholine receptor M2 Rattus norvegicus 0.899
CHEMBL1983 Serotonin 1d (5-HT1d) receptor Homo sapiens 0.820
CHEMBL3943 Histamine H1 receptor Cavia porcellus 0.815
CHEMBL216 Muscarinic acetylcholine receptor M1 Homo sapiens 0.789
CHEMBL211 Muscarinic acetylcholine receptor M2 Homo sapiens 0.751
CHEMBL245 Muscarinic acetylcholine receptor M3 Homo sapiens 0.668
CHEMBL6184 Transporter Rattus norvegicus 0.524
CHEMBL304 Norepinephrine transporter Rattus norvegicus 0.509
CHEMBL324 Serotonin 2c (5-HT2c) receptor Rattus norvegicus 0.287



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL313 Serotonin transporter Rattus norvegicus 1.000
CHEMBL338 Dopamine transporter Rattus norvegicus 1.000
CHEMBL228 Serotonin transporter Homo sapiens 1.000
CHEMBL238 Dopamine transporter Homo sapiens 1.000
CHEMBL222 Norepinephrine transporter Homo sapiens 1.000
CHEMBL6184 Transporter Rattus norvegicus 1.000
CHEMBL276 Muscarinic acetylcholine receptor M1 Rattus norvegicus 1.000
CHEMBL231 Histamine H1 receptor Homo sapiens 0.999
CHEMBL287 Sigma opioid receptor Homo sapiens 0.995
CHEMBL304 Norepinephrine transporter Rattus norvegicus 0.984
CHEMBL4245 Estrogen-related receptor gamma Homo sapiens 0.974
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.963
CHEMBL1821 Muscarinic acetylcholine receptor M4 Homo sapiens 0.920
CHEMBL1941 Histamine H2 receptor Homo sapiens 0.889
CHEMBL3943 Histamine H1 receptor Cavia porcellus 0.865
CHEMBL1983 Serotonin 1d (5-HT1d) receptor Homo sapiens 0.849
CHEMBL2035 Muscarinic acetylcholine receptor M5 Homo sapiens 0.843
CHEMBL216 Muscarinic acetylcholine receptor M1 Homo sapiens 0.773
CHEMBL211 Muscarinic acetylcholine receptor M2 Homo sapiens 0.770
CHEMBL309 Muscarinic acetylcholine receptor M2 Rattus norvegicus 0.765

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
255.4 255.1623 3.35 6 12.47 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 0 0 2 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 8.76 3 1.63 2 19 0.78

Structural Alerts

There are no structural alerts for CHEMBL657

Compound Cross References

ATC R - RESPIRATORY SYSTEM
R06 - ANTIHISTAMINES FOR SYSTEMIC USE
R06A - ANTIHISTAMINES FOR SYSTEMIC USE
R06AA - Aminoalkyl ethers
R06AA02 - diphenhydramine

D - DERMATOLOGICALS
D04 - ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
D04A - ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
D04AA - Antihistamines for topical use
D04AA32 - diphenhydramine

R - RESPIRATORY SYSTEM
R06 - ANTIHISTAMINES FOR SYSTEMIC USE
R06A - ANTIHISTAMINES FOR SYSTEMIC USE
R06AA - Aminoalkyl ethers
R06AA52 - diphenhydramine, combinations

ChemSpider ChemSpider:ZZVUWRFHKOJYTH-UHFFFAOYSA-N
DailyMed diphenhydramine hydrochloride
PubChem SID: 104171144 SID: 11111059 SID: 11111060 SID: 124879862 SID: 124879863 SID: 144203678 SID: 170466857 SID: 26751623 SID: 50100219 SID: 50104292 SID: 85148365 SID: 90341811
Wikipedia Diphenhydramine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL657



ACToR 58-73-1
BindingDB 50017674
Brenda 155303 36366
ChEBI 4636
ChemicalBook CB6196202
DrugBank DB01075
DrugCentral 916
eMolecules 716786
EPA CompTox Dashboard DTXSID4022949
FDA SRS 8GTS82S83M
Guide to Pharmacology 1224
Human Metabolome Database HMDB0001927
IBM Patent System 8609C2824D314EECCC3C15674677B37E
KEGG Ligand C06960
LINCS LSM-5581
Mcule MCULE-6260910826
MolPort MolPort-001-783-508
Nikkaji J1.390K
PDBe 2PM
PharmGKB PA449349
PubChem 3100
PubChem: Thomson Pharma 14749996
SureChEMBL SCHEMBL4064
ZINC ZINC000000020244

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/ZZVUWRFHKOJYTH-UHFFFAOYSA-N spacer
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