Details of the Drug

General Information of Drug (ID: DM1TMA3)

Drug Name
Imiquimod
Synonyms
Aldara; Beselna; Zartra; Zyclara; Imiquimod acetate; R 837; S 26308; Aldara (TN); Aldara, Imiquimod; Beselna (TN); DZ-2636; Imiquimod [USAN:INN]; MTD-39; R-837; S-26308; TMX-101; Imiquimod (JAN/USAN/INN); 1-(2-Methylpropyl)-1H-imidazole[4,5-c]quinoline-4-amine; 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine; 1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine; 1-isobutyl-1H-imidazo(4,5-c)quinolin-4-amine; 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine; 3M Brand of Imiquimod; 4-Amino-1-isobutyl-1H-imidazo(4,5-c)quinoline; 4-Amino-1-isobutyl-1H-imidazo[4,5-c]quinoline
Indication
Disease Entry ICD 11 Status REF
Alopecia areata ED70.2 Approved [1]
Condyloma 1A95 Approved [1]
Glioblastoma 2A00 Approved [1]
Melanoma 2C30 Approved [1]
Skin cancer 2C30-2C37 Approved [2]
Therapeutic Class
Antiviral Agents
Affected Organisms
Humans and other mammals
ATC Code
D06BB10: Imiquimod
D06BB: Antivirals
D06B: CHEMOTHERAPEUTICS FOR TOPICAL USE
D06: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
D: DERMATOLOGICALS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 240.3
Logarithm of the Partition Coefficient (xlogp) 2.6
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption
The drug is well absorbed through skin []
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Elimination
1% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 20 hours [4]
Water Solubility
The ability of drug to dissolve in water is measured as 0.6 mg/mL [3]
Chemical Identifiers
Formula
C14H16N4
IUPAC Name
1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine
Canonical SMILES
CC(C)CN1C=NC2=C1C3=CC=CC=C3N=C2N
InChI
InChI=1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)
InChIKey
DOUYETYNHWVLEO-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
57469
ChEBI ID
CHEMBL1282
CAS Number
99011-02-6
UNII
P1QW714R7M
DrugBank ID
DB00724
TTD ID
D06CTE
INTEDE ID
DR0864
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Toll-like receptor 7 (TLR7) TTRJ1K4 TLR7_HUMAN Agonist [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [6]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Protein Interaction/Cellular Processes [7]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Regulation of Drug Effects [8]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Protein Interaction/Cellular Processes [7]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [9]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [9]
Transforming growth factor beta-1 proprotein (TGFB1) OTV5XHVH TGFB1_HUMAN Protein Interaction/Cellular Processes [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Imiquimod FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5003).
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Imiquimod enhances IFN-gamma production and effector function of T cells infiltrating human squamous cell carcinomas of the skin. J Invest Dermatol. 2009 Nov;129(11):2676-85.
6 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
7 Cannabidiol selectively modulates interleukin (IL)-1 and IL-6 production in toll-like receptor activated human peripheral blood monocytes. Toxicology. 2021 Dec;464:153016. doi: 10.1016/j.tox.2021.153016. Epub 2021 Nov 2.
8 The Toll-like receptor agonist imiquimod is metabolized by aryl hydrocarbon receptor-regulated cytochrome P450 enzymes in human keratinocytes and mouse liver. Arch Toxicol. 2019 Jul;93(7):1917-1926.
9 Imiquimod induces apoptosis of human melanocytes. Arch Dermatol Res. 2010 May;302(4):301-6. doi: 10.1007/s00403-009-1012-0. Epub 2009 Dec 23.