Imiquimod

Imiquimod

Clinical data
Trade names	Aldara originally. Many brands available.
AHFS/Drugs.com	Monograph
MedlinePlus	a698010
License data	EU EMA: Aldara US FDA: Imiquimod
Pregnancy category	AU: B1 US: C (Risk not ruled out)
Routes of administration	Topical
ATC code	D06BB10 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Biological half-life	30 hours (topical dose), 2 hours (subcutaneous dose)
Identifiers
IUPAC name 3-(2-Methylpropyl)-3,5,8-triazatricyclo[7.4.0.02,6]trideca-1(9),2(6),4,7,10,12-hexaen-7-amine
Synonyms	1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine
CAS Number	99011-02-6 Y
PubChem CID	57469
IUPHAR/BPS	5003
DrugBank	DB00724 Y
ChemSpider	51809 Y
UNII	P1QW714R7M
KEGG	D02500 Y
ChEBI	CHEBI:36704 Y
ChEMBL	CHEMBL1282 Y
ECHA InfoCard	100.131.047
Chemical and physical data
Formula	C14H16N4
Molar mass	240.304 g/mol
3D model (Jmol)	Interactive image
SMILES n3c1ccccc1c2c(ncn2CC(C)C)c3N
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) Y Key:DOUYETYNHWVLEO-UHFFFAOYSA-N Y

Imiquimod (INN) is a prescription medication that acts as an immune response modifier and is used to treat genital warts, superficial basal cell carcinoma, and actinic keratosis. Scientists at 3M's pharmaceuticals division discovered the drug and 3M obtained the first FDA approval in 1997 under the brand Aldara. As of 2015 imiquimod is generic and is available worldwide under many brands.

Imiquimod is a patient-applied cream prescribed to treat genital warts and, secondary to surgery, for basal cell carcinoma, as well as actinic keratosis.

Side effects include local inflammatory reactions, such as blisters, a burning sensation, skin redness, dry skin, itching, skin breakdown, skin crusting or scabbing, skin drainage, skin flaking or scaling, skin ulceration, sores, swelling, as well as systemic reactions, such as fever, "flu-like" symptoms, headache, and tiredness.

People who have had an organ transplant and are taking immune-suppressing drugs should not use imiquimod.

It is known that imiquimod signals to the innate arm of the immune system through the toll-like receptor 7 (TLR7), commonly involved in pathogen recognition. Cells activated by imiquimod via TLR-7 secrete cytokines (primarily interferon-α (IFN-α), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α)). There is evidence that imiquimod, when applied to skin, can lead to the activation of Langerhans cells, which subsequently migrate to local lymph nodes to activate the adaptive immune system. Other cell types activated by imiquimod include natural killer cells, macrophages and B-lymphocytes. Overall imiquimod acts on several levels, which appear to synergistically underlie the profound antitumoral activity of the compound.