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Compound Detail

CHEMBL1282

IMIQUIMOD
💊 Approved Drug
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💊 Approved Drug
CC(C)Cn1cnc2c(N)nc3ccccc3c21

Basic Information

ChEMBL ID CHEMBL1282
Name IMIQUIMOD
Phase Approved
Structure Type MOL
InChI Key DOUYETYNHWVLEO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Aldara Imiquimod NSC-369100 NSC-759651 R-837 S-26308 S26308 Tmx-101 Zartra Zyclara
9
Targets
25
Activities
3
Assay Types
0
PK Parameters
20
Publications
10
Known Names
20
Indications
1
Mechanisms

Molecular Properties

240.3
MW (Da)
2.82
ALogP
4
HBA
1
HBD
56.7
PSA (Ų)
0.75
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Prescription
Chirality Achiral

Routes of Administration

Topical

Flags

Black Box Warning Natural Product
USAN Stem -imod
USAN Year 1991

Extended Properties

Molecular Formula C14H16N4
MW 240.31
Aromatic Rings 3
Heavy Atoms 18
NP-Likeness -0.84

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Toll-like receptor 7 agonist AGONIST Toll-like receptor 7

Indications

Carcinoma, Basal Cell Carcinoma, Basal Cell Condylomata Acuminata Keratosis Keratosis, Actinic Keratosis, Actinic Virus Diseases Influenza, Human Leishmaniasis, Cutaneous Paget Disease, Extramammary Papillomavirus Infections Scleroderma, Localized Squamous Intraepithelial Lesions Uterine Cervical Dysplasia Uterine Cervical Dysplasia Vulvar Neoplasms Bowen's Disease Breast Neoplasms Carcinoma in Situ Carcinoma, Non-Small-Cell Lung

ATC Classification

D06BB10
imiquimod
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

EC50 11 meas. best 6.7
IC50 11 meas. best 6.19
Ki 3 meas. best 5.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Toll-like receptor 7
CHEMBL5936
EC50 6.7 5.399 202.0 10
Oxidized purine nucleoside triphosphate hydrolase
CHEMBL3708265
IC50 6.19 6.19 646.0 1
Hepatitis C virus
CHEMBL379
EC50 6.0 6.0 1000.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 5.89 5.89 1288.0 1
Histamine H2 receptor
CHEMBL1941
Ki 5.83 5.83 1481.0 1
Histamine H2 receptor
CHEMBL1941
IC50 5.82 5.82 1506.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 5.58 5.58 2621.0 1
Adenosine receptor A2a
CHEMBL251
Ki 5.53 5.53 2987.0 1
Adenosine receptor A2a
CHEMBL251
IC50 5.27 5.27 5320.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.47 4.37 33500.0 2
LS174T
CHEMBL614097
IC50 4.46 4.46 34400.0 1
A-375
CHEMBL613859
IC50 4.15 4.15 70300.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Toll-like receptor 7 EC50 = 202.0 nM 6.7 Agonist activity at TLR7 (unknown origin) 38787938
Oxidized purine nucleoside triphosphate hydrolase IC50 = 646.0 nM 6.19 Inhibition of MTH1 (unknown origin) using 8-oxo-dGTP as substrate preincubated f... 26878898
Hepatitis C virus EC50 = 1000.0 nM 6.0 Antiviral activity against HCV 30639895
Alpha-1D adrenergic receptor Ki = 1288.0 nM 5.89 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
Histamine H2 receptor Ki = 1481.0 nM 5.83 DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) -
Histamine H2 receptor IC50 = 1506.0 nM 5.82 DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) -
Toll-like receptor 7 EC50 = 2120.0 nM 5.67 Agonist activity at TLR7 (unknown origin) 37163340
Toll-like receptor 7 EC50 = 2120.0 nM 5.67 Agonist activity at human TLR7 expressed in NF-kappaB-stimulated HEK293 cells as... 20481492
Toll-like receptor 7 EC50 = 2210.0 nM 5.66 Agonist activity at human TLR7 34107682
Alpha-1D adrenergic receptor IC50 = 2621.0 nM 5.58 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
Adenosine receptor A2a Ki = 2987.0 nM 5.53 DRUGMATRIX: Adenosine A2A radioligand binding (ligand: AB-MECA) -
Adenosine receptor A2a IC50 = 5320.0 nM 5.27 DRUGMATRIX: Adenosine A2A radioligand binding (ligand: AB-MECA) -
Toll-like receptor 7 EC50 = 6200.0 nM 5.21 Agonist activity at human TLR7 in HEK293 cells cotransfected with SEAP reporter ... 31247373
Toll-like receptor 7 EC50 = 6800.0 nM 5.17 Agonist activity at human TLR7 expressed in HEK-Blue cells assessed as induction... 31784317
Toll-like receptor 7 EC50 = 8290.0 nM 5.08 Agonist activity at human TLR7 in HEK-Blue hTLR7 cells assessed as increase in i... 38741265
Toll-like receptor 7 EC50 = 10700.0 nM 4.97 Agonist activity at human TLR-7 expressed in HEK293 cells after 24 hrs by SEAP r... 24383475
Toll-like receptor 7 EC50 = 11400.0 nM 4.94 Agonist activity at human TLR7 expressed in HEK cells after 8 to 12 hrs by NFkap... 29152046
Toll-like receptor 7 EC50 = 12100.0 nM 4.92 Agonist activity at human TLR7 transfected in HEK cells assessed as NFkappaB ind... 22837811
NON-PROTEIN TARGET IC50 = 33500.0 nM 4.47 Cytotoxicity against human M4Be cells after 96 hrs by MTT assay 18513976
LS174T IC50 = 34400.0 nM 4.46 Cytotoxicity against human LS174T cells after 96 hrs by MTT assay 18513976

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 232
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
31784317 10.1016/j.bmcl.2019.126788 Toll-like receptor 7/8 12
38741265 10.1021/acs.jmedchem.4c00464 Mus musculus 6
17548497 10.1128/aac.00268-07 PBMC 6
29152046 10.1021/acsmedchemlett.7b00256 PBMC 4
24383475 10.1021/jm4004957 TLR7 and TLR8 4
22837811 10.1021/ml300079e Unchecked 4
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
- 10.6019/CHEMBL3301361 ADMET 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
31247373 10.1016/j.ejmech.2019.06.030 PBMC 3
17548497 10.1128/aac.00268-07 Hepatitis C virus 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.1101/2020.04.21.054387 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
18513976 10.1016/j.bmc.2008.05.022 NON-PROTEIN TARGET 2
- 10.6019/CHEMBL3301361 No relevant target 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2

Data from ChEMBL 36 via Core Engine