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]
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Therapeutic Class

Antiviral Agents

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:36704
CAS Number: 99011-02-6
DrugBank ID: DB00724
TTD ID: D06CTE
INTEDE ID: DR0864

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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]

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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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[7]
C-C motif chemokine 2 (CCL2)	OTAD2HEL	CCL2_HUMAN	Protein Interaction/Cellular Processes	[8]
Caspase-1 (CASP1)	OTZ3YQFU	CASP1_HUMAN	Gene/Protein Processing	[9]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[10]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Biotransformations	[11]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Biotransformations	[11]
Cytochrome P450 2C19 (CYP2C19)	OTFMJYYE	CP2CJ_HUMAN	Regulation of Drug Effects	[11]
Cytochrome P450 2D6 (CYP2D6)	OTZJC802	CP2D6_HUMAN	Regulation of Drug Effects	[11]
Fibroblast growth factor 2 (FGF2)	OT7YUJ9F	FGF2_HUMAN	Gene/Protein Processing	[12]
Interleukin-1 beta (IL1B)	OT0DWXXB	IL1B_HUMAN	Gene/Protein Processing	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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	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.
8	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.
9	(9)-Tetrahydrocannabinol Suppresses Monocyte-Mediated Astrocyte Production of Monocyte Chemoattractant Protein 1 and Interleukin-6 in a Toll-Like Receptor 7-Stimulated Human Coculture. J Pharmacol Exp Ther. 2019 Oct;371(1):191-201. doi: 10.1124/jpet.119.260661. Epub 2019 Aug 5.
10	Tumor-selective induction of apoptosis and the small-molecule immune response modifier imiquimod. J Natl Cancer Inst. 2003 Aug 6;95(15):1138-49. doi: 10.1093/jnci/djg016.
11	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.
12	Imiquimod: a potential weapon against Dupuytren contracture. Med Hypotheses. 2006;66(5):991-2. doi: 10.1016/j.mehy.2005.09.052. Epub 2005 Dec 20.