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)

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
UNII: P1QW714R7M
DrugBank ID: DB00724
TTD ID: D06CTE
INTEDE ID: DR0864

Combinatorial Drugs (CBD)

Click to Jump to the Detailed CBD Information of This Drug

Repurposed Drugs (RPD)

Click to Jump to the Detailed RPD Information of This Drug

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
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]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

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	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.