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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1282
CHEMBL1282
Compound Name IMIQUIMOD
ChEMBL Synonyms ZYCLARA | S26308 | ALDARA | R-837 | IMIQUIMOD
Max Phase 4 (Approved)
Trade Names IMIQUIMOD | ALDARA | ZYCLARA
Molecular Formula C14H16N4

Additional synonyms for CHEMBL1282 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC(C)Cn1cnc2c(N)nc3ccccc3c12
Standard InChI InChI=1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10 ...
Download InChI
Standard InChI Key DOUYETYNHWVLEO-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1282

Molecule Features

CHEMBL1282 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:Y Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Toll-like receptor 7 agonist Toll-like receptor 7 FDA PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
MelanomaD008545EFO:0000389cutaneous melanoma3ClinicalTrials
MelanomaD008545EFO:0000756melanoma3ClinicalTrials
MelanomaD008545EFO:0002617metastatic melanoma3ClinicalTrials
Papillomavirus InfectionsD030361EFO:0001668human papilloma virus infection2ClinicalTrials
Scleroderma, LocalizedD012594EFO:1001361localised scleroderma3ClinicalTrials
Skin NeoplasmsD012878EFO:0004198skin neoplasm3ClinicalTrials
AstrocytomaD001254EFO:0002499anaplastic astrocytoma1ClinicalTrials
LeukemiaD007938EFO:0000565leukemia2ClinicalTrials
Lymphoma, T-Cell, CutaneousD016410EFO:0002913Cutaneous T-cell lymphoma0ClinicalTrials
Paget Disease, ExtramammaryD010145EFO:1000249Extramammary Paget Disease3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma1ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma1ClinicalTrials
Condylomata AcuminataD003218EFO:0007147anogenital venereal wart3ClinicalTrials
Hepatitis B, ChronicD019694EFO:0004197hepatitis B infection2ClinicalTrials
Leishmaniasis, CutaneousD016773EFO:0005046cutaneous Leishmaniasis3ClinicalTrials
Virus DiseasesD014777EFO:0000763viral disease4ATC
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme1ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia2ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma1ClinicalTrials
EpendymomaD004806EFO:1000028ependymoma1ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer1ClinicalTrials
HemangiomaD006391EFO:1000635hemangioma2ClinicalTrials
Influenza, HumanD007251EFO:0001669influenza infection3ClinicalTrials
OsteosarcomaD012516EFO:0000637osteosarcoma1ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma1ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma1ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001416cervical adenocarcinoma2ClinicalTrials
Carcinoma, Basal CellD002280EFO:0004193basal cell carcinoma3ClinicalTrials
Keratosis, ActinicD055623EFO:0002496actinic keratosis3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma1ClinicalTrials
SarcomaD012509EFO:1001968soft tissue sarcoma1ClinicalTrials
Uterine Cervical DysplasiaD002578EFO:1000910dysplasia of cervix3ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma2ClinicalTrials
Vulvar NeoplasmsD014846EFO:0002627vulvar intraepithelial neoplasia3ClinicalTrials
Vulvar NeoplasmsD014846EFO:0002921vulvar carcinoma3ClinicalTrials

Clinical Data

ClinicalTrials.gov IMIQUIMOD
The Cochrane Collaboration IMIQUIMOD

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 CHEMBL1282. 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
CHEMBL4975 Adenosine A1 receptor Bos taurus 0.979
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 0.709
CHEMBL256 Adenosine A3 receptor Homo sapiens 0.600
CHEMBL251 Adenosine A2a receptor Homo sapiens 0.520
CHEMBL226 Adenosine A1 receptor Homo sapiens 0.307
CHEMBL5936 Toll-like receptor 7 Homo sapiens 0.249



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5936 Toll-like receptor 7 Homo sapiens 1.000
CHEMBL251 Adenosine A2a receptor Homo sapiens 0.980
CHEMBL4975 Adenosine A1 receptor Bos taurus 0.962
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 0.922
CHEMBL4697 Hexose transporter 1 Plasmodium falciparum 0.573
CHEMBL256 Adenosine A3 receptor Homo sapiens 0.565
CHEMBL2966 Adenosine deaminase Bos taurus 0.561
CHEMBL2535 Glucose transporter Homo sapiens 0.463
CHEMBL226 Adenosine A1 receptor Homo sapiens 0.317

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
240.3 240.1375 2.82 2 56.73 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 1 0 4 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 6.28 3.01 2.89 3 18 0.75

Structural Alerts

There are 2 structural alerts for CHEMBL1282. To view alerts please click here.

Compound Cross References

ATC D - DERMATOLOGICALS
D06 - ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
D06B - CHEMOTHERAPEUTICS FOR TOPICAL USE
D06BB - Antivirals
D06BB10 - imiquimod

ChemSpider ChemSpider:DOUYETYNHWVLEO-UHFFFAOYSA-N
DailyMed imiquimod
PubChem SID: 144204536 SID: 170464691 SID: 174006731 SID: 26752301 SID: 865810
Wikipedia Imiquimod

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1282



ACToR 99011-02-6
BindingDB 50240849
ChEBI 36704
ChemicalBook CB2664655 CB9257146
DrugBank DB00724
DrugCentral 1429
eMolecules 1935723
EPA CompTox Dashboard DTXSID7041047
FDA SRS P1QW714R7M
Guide to Pharmacology 5003
Human Metabolome Database HMDB0014862
IBM Patent System 5078AF8A6A5D632C1033971C690A4214
LINCS LSM-5408
Mcule MCULE-9421195760
MolPort MolPort-002-507-845
Nikkaji J501.447F
PDBe 6T0
PharmGKB PA449972
PubChem 57469
PubChem: Drugs of the Future 12013659
PubChem: Thomson Pharma 14749564
Selleck Imiquimod
SureChEMBL SCHEMBL26136
ZINC ZINC000019632912

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