Drug Details

General Information of the Drug (ID: DR0268)
Name
Imiquimod
Synonyms
IMIQUIMOD; 99011-02-6; Aldara; Zyclara; 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine; 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine; Beselna; R 837; 4-Amino-1-isobutyl-1H-imidazo[4,5-c]quinoline; R-837; 4-Amino-1-isobutyl-1H-imidazo(4,5-c)quinoline; 1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine; S-26308; C14H16N4; 9050-31-1; UNII-P1QW714R7M; MFCD00866946; 1H-Imidazo[4,5-c]quinolin-4-amine, 1-(2-methylpropyl)-; CHEMBL1282; 1-isobutylimidazo[4,5-c]quinolin-4-amine; P1QW714R7M; 1-(2-Methylpropyl)-1H-imidazole[4,5-c]quinoline-4-amine; CHEBI:36704; S26308; 1H-Imidazo(4,5-c)quinolin-4-amine, 1-(2-methylpropyl)-; NCGC00070736-02; Zartra; Imiquimod acetate; DSSTox_CID_21047; DSSTox_RID_79617; DSSTox_GSID_41047; Aldara (TN); CAS-99011-02-6; S 26308; SR-01000611320; Imiquimodum; Imiquimod [USAN:INN:BAN]; Vyloma; MTD-39; HSDB 8129; zlchem 9; TMX 101; TMX-101; Aldara; ; ; Beselna; Imiquimod,(S); 6T0; Imiquimod - Aldara; Zyclara (TN); DZ-2636; PubChem21071; ACMC-209stx; (non-labelled)Imiquimod-d9; Imiquimod (JAN/USP/INN); SCHEMBL26136; MLS000083577; BIDD:GT0859; GTPL5003; DTXSID7041047; AOB6939; ZLA0010; HMS2090M14; HMS2232G07; HMS3373B13; HMS3715N19; HMS3747A13; Pharmakon1600-01502351; BCP05151; EBD27815; HY-B0180; Tox21_110985; AC-529; ANW-41635; BBL010772; BDBM50240849; NSC369100; NSC759651; s1211; STK583860; ZINC19632912; Imiquimod - CAS 99011-02-6; Imiquimod, >=98% (HPLC), solid; AKOS005507352; Tox21_110985_1; 1H-Imidazo[4, 1-(2-methylpropyl)-; CCG-208015; CS-2058; DB00724; KS-5218; MCULE-9421195760; NSC 369100; NSC 741062; NSC 759651; NSC-369100; NSC-759651; Imiquimod 100 microg/mL in Acetonitrile; NCGC00070736-03; NCGC00070736-04; AK209015; SMR000048307; SY017571; FT-0602727; I0747; D02500; J10325; Z-4416; 1-isobutyl-1H-imidazo [4,5-c]quinolin-4-amine; 1-isobutyl-1H-imidazo[4,5-c]quinoline-4-amine; AB00399298-05; AB00399298-06; AB00399298-07; AB00399298_08; AB00399298_09; 011I026; 1-Isobutyl-1H-imidazo[4,5-c]quinolin-4-ylamine; A845945; Q423417; 1-(2-methylpropyl)-4-imidazo[4,5-c]quinolinamine; SR-01000611320-2; SR-01000611320-3; BRD-K26657438-001-01-2; BRD-K26657438-001-13-7; 1-(2-methylpropyl)-1Himidazo[4,5-c]quinolin-4-amine; 1-(2-methylpropyl)-1H-imidazo[4,5-c]-quinolin-4-amine; 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine;; Imiquimod, United States Pharmacopeia (USP) Reference Standard; 4-Amino- 1-isobutyl-1H-imidazo[4,5-c]quinoline; 1-(2-Methylpropyl)-1H-imidazo[4,5-C]quinolin-4-amine
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Molecular Type
Small molecule
Disease Skin cancer [ICD-11: 2C30-2C37] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C14H16N4
PubChem CID
57469
Canonical SMILES
CC(C)CN1C=NC2=C1C3=CC=CC=C3N=C2N
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
CAS Number
CAS 99011-02-6
ChEBI ID
CHEBI:36704
TTD Drug ID
D06CTE
DrugBank ID
DB00724
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Tazarotene      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 Tazarotene enhanced the penetration of imiquimod, and could be a therapeutic option in cases where surgical intervention is not possible.
          Tretinoin      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model A case report
                    Experimental
                    Result(s)		 Combination of imiquimod, 5-fluorouracil, and tretinoin is an effective viable treatment modality for treating melanoma in situ during a pandemic with telemedicine.
Target and Pathway
Target(s) Toll-like receptor 7 (TLR7)  Molecule Info  [4]
KEGG Pathway Toll-like receptor signaling pathway Click to Show/Hide
2 Measles
3 Influenza A
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
Panther Pathway Toll receptor signaling pathway Click to Show/Hide
Reactome Trafficking and processing of endosomal TLR Click to Show/Hide
2 TRAF6 mediated IRF7 activation in TLR7/8 or 9 signaling
3 TRAF6 mediated induction of NFkB and MAP kinases upon TLR7/8 or 9 activation
4 MyD88 dependent cascade initiated on endosome
WikiPathways Toll-like receptor signaling pathway Click to Show/Hide
2 Toll-Like Receptors Cascades
3 MyD88 dependent cascade initiated on endosome
4 Trafficking and processing of endosomal TLR
5 Regulation of toll-like receptor signaling pathway
References
Reference 1 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).
Reference 2 Lentigo maligna successfully treated with combination therapy of topical tazarotene and imiquimod. Clin Exp Dermatol. 2017 Jun;42(4):468-470.
Reference 3 Treating Melanoma in Situ During a Pandemic with Telemedicine and a Combination of Imiquimod, 5-Fluorouracil, and Tretinoin. Dermatol Ther (Heidelb). 2021 Feb;11(1):307-314.
Reference 4 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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