Imiquimod

Imiquimod
Clinical data
Trade names	Aldara, others
Other names	1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine
AHFS/Drugs.com	Monograph
MedlinePlus	a698010
License data	EU EMA: by INN; US DailyMed: Imiquimod;
Pregnancy; category	AU: B1; ;
Routes of; administration	Topical
ATC code	D06BB10 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Elimination 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;
CAS Number	99011-02-6 ;
PubChem CID	57469;
IUPHAR/BPS	5003;
DrugBank	DB00724 ;
ChemSpider	51809 ;
UNII	P1QW714R7M;
KEGG	D02500 ;
ChEBI	CHEBI:36704 ;
ChEMBL	ChEMBL1282 ;
CompTox Dashboard (EPA)	DTXSID7041047 ;
ECHA InfoCard	100.131.047
Chemical and physical data
Formula	C14H16N4
Molar mass	240.310 g·mol−1
3D model (JSmol)	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) ; Key:DOUYETYNHWVLEO-UHFFFAOYSA-N ;
	(verify)

Imiquimod, sold under the brand name Aldara among others, is a medication that acts as an immune response modifier that is used to treat genital warts, superficial basal cell carcinoma, and actinic keratosis.^[4]

Scientists at 3M's pharmaceuticals division discovered the drug and 3M obtained the first FDA approval in 1997. As of 2015, imiquimod is generic and is available worldwide under many brands. In 2021, it was the 290th most commonly prescribed medication in the United States, with more than 600,000 prescriptions.^[5]^[6]

^ Cite error: The named reference drugnames was invoked but never defined (see the help page).
^ "Imiquimod topical Use During Pregnancy". Drugs.com. 29 May 2019. Retrieved 14 July 2020.
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ "Imiquimod Topical". MedlinePlus. National Library of Medicine. Retrieved 2 June 2021.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Imiquimod - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

[drugnames-1] Cite error: The named reference drugnames was invoked but never defined (see the help page).

[Drugs.com_pregnancy-2] "Imiquimod topical Use During Pregnancy". Drugs.com. 29 May 2019. Retrieved 14 July 2020.

[FDA-AllBoxedWarnings-3] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[4] "Imiquimod Topical". MedlinePlus. National Library of Medicine. Retrieved 2 June 2021.

[5] "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[6] "Imiquimod - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Clinical data

Trade names	Aldara, others^[1]
Other names	1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine
AHFS/Drugs.com	Monograph
MedlinePlus	a698010
License data	EU EMA: by INN US DailyMed: Imiquimod
Pregnancy category	AU: B1^[2]
Routes of administration	Topical
ATC code	D06BB10 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: WARNING^[3]Rx-only EU: Rx-only
Pharmacokinetic data
Elimination half-life	30 hours (topical dose), 2 hours (subcutaneous dose)
Identifiers
IUPAC name 3-(2-Methylpropyl)-3,5,8-triazatricyclo[7.4.0.0^2,6]trideca-1(9),2(6),4,7,10,12-hexaen-7-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
CompTox Dashboard (EPA)	DTXSID7041047
ECHA InfoCard	100.131.047
Chemical and physical data
Formula	C₁₄H₁₆N₄
Molar mass	240.310 g·mol⁻¹
3D model (JSmol)	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
(verify)