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
Skin cancer 2C30-2C37 Approved [1], [2]
Therapeutic Class
Antiviral Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 240.3
Topological Polar Surface Area (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 [3]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [4]
Elimination
1% of drug is excreted from urine in the unchanged form [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 20 hours [5]
Water Solubility
The ability of drug to dissolve in water is measured as 0.6 mg/mL [4]
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
CHEBI:36704
CAS Number
99011-02-6
DrugBank ID
DB00724
TTD ID
D06CTE
INTEDE ID
DR0864

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 [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [7]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

ICD Disease Classification 02 Neoplasm
Disease Class ICD-11: 2C82 Prostate cancer
The Studied Tissue Skin
The Studied Disease Skin cancer [ICD-11:2C82]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Toll-like receptor 7 (TLR7) DTT TLR7 3.32E-25 0.44 0.88
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 5.21E-12 -2.23E-01 -4.75E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.29E-36 -3.75E-01 -1.06E+00
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

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4 BDDCS applied to over 900 drugs
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 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.
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