Identification

Name
Imiquimod
Accession Number
DB00724  (APRD01030)
Type
Small Molecule
Groups
Approved, Investigational
Description

Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist. Imiquimod is commonly used topically to treat warts on the skin of the genital and anal areas. Imiquimod does not cure warts, and new warts may appear during treatment. Imiquimod does not fight the viruses that cause warts directly, however, it does help to relieve and control wart production. Miquimod is also used to treat a skin condition of the face and scalp called actinic keratoses and certain types of skin cancer called superficial basal cell carcinoma.

Structure
Thumb
Synonyms
  • 1-Isobutyl-1H-imidazo[4,5-c]quinolin-4-amine
  • 4-Amino-1-isobutyl-1H-imidazo(4,5-c)quinoline
  • Imiquimod
  • Imiquimodum
  • R 837
  • Zartra
External IDs
R-837 / S 26308 / S26308
Product Ingredients
IngredientUNIICASInChI Key
Imiquimod acetateNot AvailableNot AvailableNot applicable
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AldaraCream50 mg/gTopicalValeant Pharmaceuticals North America2011-11-28Not applicableUs
Aldara PCream5 %TopicalValeant Canada Lp Valeant Canada S.E.C.1999-07-05Not applicableCanada
ImiquimodCream50 mg/1000mgTopicalPerrigo New York Inc.2010-04-202017-10-31Us
Imiquimod 5%Cream50 mgTopicalValeant Canada Lp Valeant Canada S.E.C.Not applicableNot applicableCanada
VylomaCream3.75 %TopicalValeant Canada Lp Valeant Canada S.E.C.2011-04-19Not applicableCanada
ZyclaraCream37.5 mg/gTopicalValeant Pharmaceuticals North America2012-01-01Not applicableUs
ZyclaraCream2.5 mg/gTopicalValeant Pharmaceuticals North America2012-02-29Not applicableUs
ZyclaraCream3.75 %TopicalValeant Canada Lp Valeant Canada S.E.C.2010-01-27Not applicableCanada
ZyclaraCream37.5 mg/gTopicalValeant Pharmaceuticals North America2011-11-28Not applicableUs
ZyclaraCream2.5 %TopicalValeant Canada Lp Valeant Canada S.E.C.Not applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-imiquimodCream5 %TopicalApotex Corporation2013-12-31Not applicableCanada
ImiquimodCream50 mg/gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2010-02-25Not applicableUs
ImiquimodCream12.5 mg/.25gTopicalPerrigo New York Inc.2010-11-09Not applicableUs
ImiquimodCream50 mg/1000mgTopicalApotex Corporation2012-09-14Not applicableUs
ImiquimodCream50 mg/gTopicalTaro Pharmaceuticals U.S.A., Inc.2011-04-15Not applicableUs
ImiquimodCream50 mg/gTopicalStrides Shasun Limited2014-06-24Not applicableUs
ImiquimodCream50 mg/gTopicalTaro Pharmaceutical Industries, Ltd.2011-04-15Not applicableUs
ImiquimodCream50 mg/gTopicalGlenmark Pharmaceuticals Inc.,Usa2012-03-06Not applicableUs
ImiquimodCream50 mg/gTopicalPhysicians Total Care, Inc.2010-09-22Not applicableUs
ImiquimodCream50 mg/gTopicalImpax Generics2011-02-282017-07-06Us
International/Other Brands
Beselna (Mochida) / Imimore (Panalab) / Imiquad (Glenmark) / Labimiq (ITF - Labomed) / Li Di (Mingxin Pharmaceutical) / Miquimod (Lazar) / Nan Bo (Topfond Pharmaceutical) / Nilwart (Dr. Reddy's) / Omiquidar (Darier) / Tian Rui (Yangtze River Pharma) / Vetland (Landsteiner) / You Care (Nang Kuang) / Youbiqing (The United Laboratories Ltd)
Categories
UNII
P1QW714R7M
CAS number
99011-02-6
Weight
Average: 240.3036
Monoisotopic: 240.137496532
Chemical Formula
C14H16N4
InChI Key
DOUYETYNHWVLEO-UHFFFAOYSA-N
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)
IUPAC Name
1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
SMILES
CC(C)CN1C=NC2=C1C1=CC=CC=C1N=C2N

Pharmacology

Indication

For the topical treatment of clinically typical, nonhyperkeratotic, nonhypertrophic actinic keratoses on the face or scalp in immunocompetent adults. Also indicated for the treatment of external genital and perianal warts/condyloma acuminata in individuals 12 years old and above.

Structured Indications
Pharmacodynamics

Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist. Imiquimod is commonly used topically to treat warts on the skin of the genital and anal areas. Imiquimod does not cure warts, and new warts may appear during treatment. Imiquimod does not fight the viruses that cause warts directly, however, it does help to relieve and control wart production. It is not used on warts inside the vagina, penis, or rectum. Imiquimod is also used to treat a skin condition of the face and scalp called actinic keratoses. Imiquimod can also be used to treat certain types of skin cancer called superficial basal cell carcinoma. Imiquimod is particularly useful on areas where surgery or other treatments may be difficult, complicated or otherwise undesirable, especially the face and lower legs.

Mechanism of action

Imiquimod's mechanism of action is via stimulation of innate and acquired immune responses, which ultimately leads to inflammatory cell infiltration within the field of drug application followed by apoptosis of diseased tissue. Imiquimod does not have direct antiviral activity. Studies of mice show that imiquimod may induce cytokines, including interferon-alpha (IFNA) as well as several IFNA genes (IFNA1, IFNA2, IFNA5, IFNA6, and IFNA8) as well as the IFNB gene. Imiquimod also induced the expression of interleukin (IL)-6, IL-8, and tumor necrosis factor alpha genes. In the treatment of basal cell carcinoma, Imiquimod appears to act as a toll-like receptor-7 agonist, and is thought to exert its anti-tumor effect via modification of the immune response and stimulation of apoptosis in BCC cells. In treating basal cell carcinoma it may increase the infiltration of lymphocytes, dendritic cells, and macrophages into the tumor lesion.

TargetActionsOrganism
AToll-like receptor 7
agonist
Human
UToll-like receptor 8
agonist
Human
Absorption

Well absorbed through skin (as a cream)

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

20 hours (topical dose), 2 hours (subcutaneous dose)

Clearance
Not Available
Toxicity

Symptoms of overdose include flu-like symptoms, such as fever, fatigue, headache, nausea, diarrhoea and muscle pain.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Imiquimod can be increased when it is combined with Abiraterone.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Imiquimod.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Imiquimod.Experimental
AmiodaroneThe metabolism of Imiquimod can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Imiquimod can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Imiquimod can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Imiquimod can be decreased when combined with Atomoxetine.Approved
AzithromycinThe metabolism of Imiquimod can be decreased when combined with Azithromycin.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Imiquimod.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Imiquimod.Approved, Investigational
BoceprevirThe metabolism of Imiquimod can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Imiquimod can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Imiquimod can be decreased when it is combined with Bosentan.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Imiquimod.Approved
CaffeineThe metabolism of Imiquimod can be decreased when combined with Caffeine.Approved
CarbamazepineThe metabolism of Imiquimod can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Imiquimod can be increased when it is combined with Ceritinib.Approved
CitalopramThe metabolism of Imiquimod can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Imiquimod can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Imiquimod can be decreased when combined with Clemastine.Approved
Clostridium tetani toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Clostridium tetani toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Imiquimod.Approved
ClotrimazoleThe metabolism of Imiquimod can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Imiquimod can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Imiquimod can be increased when it is combined with Conivaptan.Approved, Investigational
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Imiquimod.Approved
CrizotinibThe metabolism of Imiquimod can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Imiquimod.Approved, Investigational
CyclosporineThe metabolism of Imiquimod can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Imiquimod.Experimental
Cyproterone acetateThe serum concentration of Imiquimod can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Imiquimod can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Imiquimod can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Imiquimod can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Imiquimod can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Imiquimod can be decreased when combined with Delavirdine.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Imiquimod.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Imiquimod.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Imiquimod.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Imiquimod.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Imiquimod.Approved
DihydroergotamineThe metabolism of Imiquimod can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Imiquimod can be decreased when combined with Diltiazem.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Imiquimod.Approved, Investigational
DosulepinThe metabolism of Imiquimod can be decreased when combined with Dosulepin.Approved
DoxycyclineThe metabolism of Imiquimod can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Imiquimod can be decreased when combined with Dronedarone.Approved
EnzalutamideThe serum concentration of Imiquimod can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Imiquimod can be decreased when combined with Erythromycin.Approved, Vet Approved
FingolimodImiquimod may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FluconazoleThe metabolism of Imiquimod can be decreased when combined with Fluconazole.Approved
FluvoxamineThe metabolism of Imiquimod can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Imiquimod can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Imiquimod can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Imiquimod can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Imiquimod can be increased when it is combined with Fusidic Acid.Approved
G17DTThe therapeutic efficacy of G17DT can be decreased when used in combination with Imiquimod.Investigational
GI-5005The therapeutic efficacy of GI-5005 can be decreased when used in combination with Imiquimod.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Imiquimod.Experimental
Hepatitis A VaccineThe therapeutic efficacy of Hepatitis A Vaccine can be decreased when used in combination with Imiquimod.Approved
Hepatitis B Vaccine (Recombinant)The therapeutic efficacy of Hepatitis B Vaccine (Recombinant) can be decreased when used in combination with Imiquimod.Approved, Withdrawn
IdelalisibThe serum concentration of Imiquimod can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Imiquimod can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Imiquimod can be decreased when combined with Indinavir.Approved
INGN 201The therapeutic efficacy of INGN 201 can be decreased when used in combination with Imiquimod.Investigational
INGN 225The therapeutic efficacy of INGN 225 can be decreased when used in combination with Imiquimod.Investigational
IsavuconazoniumThe metabolism of Imiquimod can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Imiquimod can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Imiquimod can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Imiquimod can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Imiquimod can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Imiquimod.Experimental
LeflunomideThe risk or severity of adverse effects can be increased when Imiquimod is combined with Leflunomide.Approved, Investigational
LidocaineThe metabolism of Imiquimod can be decreased when combined with Lidocaine.Approved, Vet Approved
LobeglitazoneThe metabolism of Imiquimod can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Imiquimod can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Imiquimod can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Imiquimod can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Imiquimod can be increased when combined with Lumacaftor.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Imiquimod.Experimental
MexiletineThe metabolism of Imiquimod can be decreased when combined with Mexiletine.Approved
MidostaurinThe metabolism of Imiquimod can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Imiquimod can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Imiquimod can be decreased when it is combined with Mitotane.Approved
NatalizumabThe risk or severity of adverse effects can be increased when Imiquimod is combined with Natalizumab.Approved, Investigational
NefazodoneThe metabolism of Imiquimod can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Imiquimod can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Imiquimod can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Imiquimod can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Imiquimod can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Imiquimod can be decreased when combined with Olaparib.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Imiquimod.Experimental, Investigational
OsimertinibThe serum concentration of Imiquimod can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Imiquimod.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Imiquimod.Approved, Vet Approved
PalbociclibThe serum concentration of Imiquimod can be increased when it is combined with Palbociclib.Approved
Peginterferon alfa-2bThe serum concentration of Imiquimod can be increased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Imiquimod can be increased when combined with Pentobarbital.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Imiquimod.Experimental
PhenobarbitalThe metabolism of Imiquimod can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Imiquimod can be increased when combined with Phenytoin.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Imiquimod.Approved, Investigational
PosaconazoleThe metabolism of Imiquimod can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Imiquimod can be increased when combined with Primidone.Approved, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Imiquimod.Experimental
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Imiquimod is combined with Rabies virus inactivated antigen, A.Approved
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with Imiquimod.Approved
RanolazineThe metabolism of Imiquimod can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Imiquimod can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Imiquimod can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Imiquimod can be increased when combined with Rifapentine.Approved
RindopepimutThe therapeutic efficacy of Rindopepimut can be decreased when used in combination with Imiquimod.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Imiquimod.Approved
RopiniroleThe metabolism of Imiquimod can be decreased when combined with Ropinirole.Approved, Investigational
Rotavirus VaccineThe therapeutic efficacy of Rotavirus Vaccine can be decreased when used in combination with Imiquimod.Approved
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Imiquimod.Approved
Salmonella typhi ty21a live antigenThe therapeutic efficacy of Salmonella typhi ty21a live antigen can be decreased when used in combination with Imiquimod.Approved
SaquinavirThe metabolism of Imiquimod can be decreased when combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Imiquimod can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Imiquimod can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Imiquimod can be increased when it is combined with Simeprevir.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Imiquimod.Approved
SRP 299The therapeutic efficacy of SRP 299 can be decreased when used in combination with Imiquimod.Investigational
St. John's WortThe serum concentration of Imiquimod can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Imiquimod can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Imiquimod can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Imiquimod.Approved, Investigational
TecemotideThe therapeutic efficacy of Tecemotide can be decreased when used in combination with Imiquimod.Investigational
TelaprevirThe metabolism of Imiquimod can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Imiquimod can be decreased when combined with Telithromycin.Approved
Tenofovir disoproxilThe metabolism of Imiquimod can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TeriflunomideThe serum concentration of Imiquimod can be decreased when it is combined with Teriflunomide.Approved
TG4010The therapeutic efficacy of TG4010 can be decreased when used in combination with Imiquimod.Investigational
TheophyllineThe metabolism of Imiquimod can be decreased when combined with Theophylline.Approved
TiclopidineThe metabolism of Imiquimod can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Imiquimod can be decreased when it is combined with Tocilizumab.Approved
TofacitinibImiquimod may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Imiquimod.Approved, Investigational
VemurafenibThe serum concentration of Imiquimod can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Imiquimod can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Imiquimod can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Imiquimod can be decreased when combined with Voriconazole.Approved, Investigational
Yellow fever vaccineThe therapeutic efficacy of Yellow fever vaccine can be decreased when used in combination with Imiquimod.Approved
ZiprasidoneThe metabolism of Imiquimod can be decreased when combined with Ziprasidone.Approved
Zoster vaccineThe therapeutic efficacy of Zoster vaccine can be decreased when used in combination with Imiquimod.Approved
ZucapsaicinThe metabolism of Imiquimod can be decreased when combined with Zucapsaicin.Approved
Food Interactions
Not Available

References

Synthesis Reference
US4689338
General References
  1. van Egmond S, Hoedemaker C, Sinclair R: Successful treatment of perianal Bowen's disease with imiquimod. Int J Dermatol. 2007 Mar;46(3):318-9. [PubMed:17343595]
  2. Hemmi H, Kaisho T, Takeuchi O, Sato S, Sanjo H, Hoshino K, Horiuchi T, Tomizawa H, Takeda K, Akira S: Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway. Nat Immunol. 2002 Feb;3(2):196-200. Epub 2002 Jan 22. [PubMed:11812998]
  3. Bilu D, Sauder DN: Imiquimod: modes of action. Br J Dermatol. 2003 Nov;149 Suppl 66:5-8. [PubMed:14616337]
  4. Miller RL, Gerster JF, Owens ML, Slade HB, Tomai MA: Imiquimod applied topically: a novel immune response modifier and new class of drug. Int J Immunopharmacol. 1999 Jan;21(1):1-14. [PubMed:10411278]
External Links
Human Metabolome Database
HMDB14862
KEGG Drug
D02500
PubChem Compound
57469
PubChem Substance
46505394
ChemSpider
51809
BindingDB
50240849
ChEBI
36704
ChEMBL
CHEMBL1282
Therapeutic Targets Database
DAP000278
PharmGKB
PA449972
HET
6T0
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Imiquimod
ATC Codes
D06BB10 — Imiquimod
AHFS Codes
  • 84:92.00 — Misc. Skin and Mucous Membrane Agents
PDB Entries
5lbt
FDA label
Download (144 KB)
MSDS
Download (36.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentMetastatic Melanoma / Stage IIIB Cutaneous Melanoma AJCC v7 / Stage IIIC Cutaneous Melanoma AJCC v7 / Stage IV Cutaneous Melanoma AJCC v6 and v71
0RecruitingTreatmentHigh Risk WHO Grade II Glioma / Recurrent/Post-Chemotherapy WHO Grade II Glioma1
0RecruitingTreatmentLymphoma, T-Cell, Cutaneous1
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentActinic Keratosis (AK)1
1CompletedTreatmentAnaplastic Astrocytoma (AA) / Ependymomas / Glioblastomas / Medulloblastomas / Neoplasms, Brain1
1CompletedTreatmentCutaneous Neurofibromas / Neurofibromatosis Type 11
1CompletedTreatmentDiffuse Intrinsic Pontine Glioma (DIPG)1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentMalignant Melanoma1
1CompletedTreatmentMelanoma1
1CompletedTreatmentMelanoma (Skin)1
1CompletedTreatmentMelanoma (Skin) / Metastatic Cancers1
1CompletedTreatmentNon-Melanomatous Skin Cancer1
1Not Yet RecruitingTreatmentHigh Grade Cervical Intraepithelial Neoplasia / P16 Positive Neoplastic Cells Present1
1RecruitingOtherHealthy Volunteers1
1RecruitingTreatmentAdenocarcinoma of the Prostate1
1RecruitingTreatmentCancer, Breast / Malignant Neoplasm of Stomach1
1RecruitingTreatmentCervical Cancers / HPV Disease / Human Papilomavirus / Precancerous Conditions1
1RecruitingTreatmentSarcoma, Bone / Sarcomas / Soft Tissue Sarcoma (STS)1
1TerminatedTreatmentGlioblastomas1
1TerminatedTreatmentHPV 16- and/or HPV 18-Infected Women With Normal Cytology, ASCUS, or LSIL1
1, 2Active Not RecruitingTreatmentCancer, Breast / Metastatic Breast Cancer (MBC) / Recurrent Breast Cancer1
1, 2Active Not RecruitingTreatmentRecurrent Prostate Cancer1
1, 2CompletedTreatmentCarcinoma, Colorectal1
2Active Not RecruitingTreatmentCancer, Ovarian / Fallopian Tube Cancer / Primary Peritoneal Cancer1
2Active Not RecruitingTreatmentMale Breast Cancer / Metastases to skin / Recurrent Breast Cancer / Stage IV Breast Cancer1
2CompletedNot AvailableActinic Keratosis (AK)1
2CompletedBasic ScienceVaginal Infections / Vaginal Inflammation1
2CompletedPreventionCervical Cancers / Precancerous Conditions1
2CompletedPreventionInfluenza Vaccines1
2CompletedTreatmentActinic Keratosis (AK)2
2CompletedTreatmentCancer, Breast / Neoplasms, Breast1
2CompletedTreatmentCarcinoma in Situ / Non Muscle Invasive Bladder Cancer1
2CompletedTreatmentExternal Genital Warts1
2CompletedTreatmentHemangioma, Capillary1
2CompletedTreatmentHigh-Risk Melanoma1
2CompletedTreatmentHpv1
2CompletedTreatmentLeishmaniasis, Cutaneous1
2CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2CompletedTreatmentMalignant Melanoma1
2CompletedTreatmentPort Wine Stains1
2Not Yet RecruitingTreatmentUterine Cervical Neoplasm1
2RecruitingTreatmentCervical Dysplasia / Cervical Intraepithelial Neoplasia (CIN)1
2RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL)1
2RecruitingTreatmentNeoplasms, Vulvar1
2TerminatedPreventionChronic Lymphocytic Leukaemia (CLL)1
2, 3Active Not RecruitingPreventionHutchinson's Melanotic Freckle1
2, 3Active Not RecruitingTreatmentCervical Intraepithelial Neoplasia (CIN)1
2, 3CompletedTreatmentCervical Intraepithelial Neoplasia (CIN)1
2, 3Unknown StatusTreatmentBowens Disease1
3CompletedNot AvailableActinic Keratosis (AK)2
3CompletedNot AvailableKeratosis1
3CompletedDiagnosticActinic Keratosis (AK)1
3CompletedPreventionInfluenza Viral Infections1
3CompletedTreatmentActinic Keratosis (AK)7
3CompletedTreatmentBasal Cell Carcinoma (BCC)3
3CompletedTreatmentLeishmaniasis, Cutaneous1
3CompletedTreatmentNon-Melanomatous Skin Cancer1
3CompletedTreatmentScleroderma, Localized1
3CompletedTreatmentSuperficial Basal Cell Carcinoma1
3CompletedTreatmentVenereal Warts2
3Enrolling by InvitationTreatmentPaget Disease, Extramammary1
3Not Yet RecruitingTreatmentAnogenital Human Papillomavirus Infection / Condyloma Anal1
3Not Yet RecruitingTreatmentCervical Intraepithelial Neoplasia (CIN)1
3RecruitingPreventionAnal Carcinoma / High-Grade Squamous Intraepithelial Lesions / Human Immunodeficiency Virus (HIV) Infections / Human Papilloma Virus Infection1
3RecruitingTreatmentAnal Intraepithelial Neoplasia (AIN) / High-Grade Squamous Intraepithelial Lesions / Human Immunodeficiency Virus (HIV) Infections1
3RecruitingTreatmentHutchinson's Melanotic Freckle1
3RecruitingTreatmentLentigo Maligna Melanoma (Head or Neck)1
3RecruitingTreatmentNodular Basal Cell Carcinoma1
3RecruitingTreatmentVulvar Intraepithelial Neoplasia1
3TerminatedTreatmentCervical Intraepithelial Neoplasia (CIN)2
3WithdrawnTreatmentMorphoea1
4Active Not RecruitingTreatmentActinic Keratosis (AK)2
4CompletedNot AvailableAlopecia Areata (AA)1
4CompletedTreatmentActinic Cheilitis1
4CompletedTreatmentActinic Keratosis (AK)3
4CompletedTreatmentAlopecia Areata (AA)1
4CompletedTreatmentBasal Cell Carcinoma (BCC)3
4CompletedTreatmentHutchinson's Melanotic Freckle1
4CompletedTreatmentKeratosis2
4CompletedTreatmentVenereal Warts1
4CompletedTreatmentWarts1
4TerminatedTreatmentActinic Keratosis (AK)2
4TerminatedTreatmentPlantar Warts1
4Unknown StatusNot AvailableActinic Keratosis (AK)1
4Unknown StatusTreatmentActinic Keratosis (AK)1
4Unknown StatusTreatmentBasal Cell Carcinoma (BCC)1
4WithdrawnTreatmentAnal Intraepithelial Neoplasia (AIN) / Human Immunodeficiency Virus (HIV) / Human Papilloma Virus (HPV)1
Not AvailableActive Not RecruitingTreatmentVulvar Cancers1
Not AvailableCompletedNot AvailableActinic Keratosis (AK)1
Not AvailableCompletedPreventionChronic Illnesses1
Not AvailableCompletedTreatmentActinic Keratosis (AK)1
Not AvailableCompletedTreatmentCancers / Hutchinson's Melanotic Freckle1
Not AvailableCompletedTreatmentPort Wine Stains1
Not AvailableCompletedTreatmentSolar Elastosis1
Not AvailableNot Yet RecruitingTreatmentMycosis Fungoides (MF)1
Not AvailableRecruitingBasic ScienceNormal Skin / Photoaged Skin1
Not AvailableRecruitingTreatmentCervical Intraepithelial Neoplasia (CIN 2/3) / HPV16+1
Not AvailableRecruitingTreatmentCervical Intraepithelial Neoplasia (CIN)1
Not AvailableRecruitingTreatmentCervical Intraepithelial Neoplasia 31
Not AvailableRecruitingTreatmentEpendymomas1
Not AvailableTerminatedNot AvailablePsoriasis1
Not AvailableUnknown StatusTreatmentBasal Cell Carcinoma (BCC)1

Pharmacoeconomics

Manufacturers
  • Graceway pharmaceuticals llc
  • Nycomed us inc
  • Graceway Pharmaceuticals, LLC
Packagers
Dosage forms
FormRouteStrength
CreamTopical5 %
CreamTopical12.5 mg/.25g
CreamTopical50 mg/1000mg
CreamTopical50 mg/g
CreamTopical50 mg
CreamTopical2.5 mg/g
CreamTopical2.5 %
CreamTopical3.75 %
CreamTopical37.5 mg/g
Prices
Unit descriptionCostUnit
Aldara 5% Cream Pack46.99USD pack
Imiquimod 5% Cream Packet42.89USD packet
Imiquimod 5% cream33.17USD each
Aldara 5% cream26.04USD each
Zyclara 3.75% cream24.43USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4689338No1992-08-252009-08-25Us
US7696159Yes2004-10-012024-10-01Us
US8222270No2009-12-112029-12-11Us
US8236816No2009-12-112029-12-11Us
US8299109No2009-12-112029-12-11Us
US8598196No2009-08-182029-08-18Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)292-294 °CNot Available
water solubilityPoorly solubleNot Available
logP2.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.247 mg/mLALOGPS
logP2.83ALOGPS
logP2.65ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area56.73 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity72.54 m3·mol-1ChemAxon
Polarizability26.67 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9967
Blood Brain Barrier+0.955
Caco-2 permeable+0.5995
P-glycoprotein substrateNon-substrate0.5137
P-glycoprotein inhibitor INon-inhibitor0.8797
P-glycoprotein inhibitor IIInhibitor0.6949
Renal organic cation transporterNon-inhibitor0.5928
CYP450 2C9 substrateNon-substrate0.8625
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.51
CYP450 1A2 substrateInhibitor0.8751
CYP450 2C9 inhibitorNon-inhibitor0.8182
CYP450 2D6 inhibitorInhibitor0.7628
CYP450 2C19 inhibitorNon-inhibitor0.634
CYP450 3A4 inhibitorNon-inhibitor0.5131
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6829
Ames testAMES toxic0.8884
CarcinogenicityNon-carcinogens0.8917
BiodegradationNot ready biodegradable0.9916
Rat acute toxicity2.5683 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9546
hERG inhibition (predictor II)Inhibitor0.5422
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000f-2970000000-08cb009f804dd3b43f69
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-2910000000-58faefee0903c8967370

Taxonomy

Description
This compound belongs to the class of organic compounds known as imidazoquinolines. These are aromatic heterocyclic compounds containing an imidazole ring fused to a quinoline ring system. In some configurations, the imidazole ring shares a nitrogen atom with the quinoline moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Imidazoquinolines
Direct Parent
Imidazoquinolines
Alternative Parents
Aminoquinolines and derivatives / Imidazo-[4,5-c]pyridines / Aminopyridines and derivatives / N-substituted imidazoles / Imidolactams / Benzenoids / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds
show 1 more
Substituents
Imidazoquinoline / Aminoquinoline / Imidazopyridine / Imidazo-[4,5-c]pyridine / Aminopyridine / N-substituted imidazole / Pyridine / Imidolactam / Benzenoid / Azole
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
imidazoquinoline (CHEBI:36704)

Targets

Details
1. Toll-like receptor 7
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Transmembrane signaling receptor activity
Specific Function
Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. TLR7 i...
Gene Name
TLR7
Uniprot ID
Q9NYK1
Uniprot Name
Toll-like receptor 7
Molecular Weight
120920.8 Da
References
  1. Gibson SJ, Lindh JM, Riter TR, Gleason RM, Rogers LM, Fuller AE, Oesterich JL, Gorden KB, Qiu X, McKane SW, Noelle RJ, Miller RL, Kedl RM, Fitzgerald-Bocarsly P, Tomai MA, Vasilakos JP: Plasmacytoid dendritic cells produce cytokines and mature in response to the TLR7 agonists, imiquimod and resiquimod. Cell Immunol. 2002 Jul-Aug;218(1-2):74-86. [PubMed:12470615]
  2. Akira S, Hemmi H: Recognition of pathogen-associated molecular patterns by TLR family. Immunol Lett. 2003 Jan 22;85(2):85-95. [PubMed:12527213]
  3. Dummer R, Urosevic M, Kempf W, Hoek K, Hafner J, Burg G: Imiquimod in basal cell carcinoma: how does it work? Br J Dermatol. 2003 Nov;149 Suppl 66:57-8. [PubMed:14616353]
  4. Otero M, Calarota SA, Felber B, Laddy D, Pavlakis G, Boyer JD, Weiner DB: Resiquimod is a modest adjuvant for HIV-1 gag-based genetic immunization in a mouse model. Vaccine. 2004 Apr 16;22(13-14):1782-90. [PubMed:15068862]
  5. Ambach A, Bonnekoh B, Nguyen M, Schon MP, Gollnick H: Imiquimod, a Toll-like receptor-7 agonist, induces perforin in cytotoxic T lymphocytes in vitro. Mol Immunol. 2004 Apr;40(18):1307-14. [PubMed:15072849]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Single-stranded rna binding
Specific Function
Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. Acts v...
Gene Name
TLR8
Uniprot ID
Q9NR97
Uniprot Name
Toll-like receptor 8
Molecular Weight
119826.82 Da
References
  1. Dummer R, Urosevic M, Kempf W, Hoek K, Hafner J, Burg G: Imiquimod in basal cell carcinoma: how does it work? Br J Dermatol. 2003 Nov;149 Suppl 66:57-8. [PubMed:14616353]
  2. Zhu J, Lai K, Brownile R, Babiuk LA, Mutwiri GK: Porcine TLR8 and TLR7 are both activated by a selective TLR7 ligand, imiquimod. Mol Immunol. 2008 Jun;45(11):3238-43. doi: 10.1016/j.molimm.2008.02.028. Epub 2008 Apr 24. [PubMed:18439678]
  3. Gorden KB, Gorski KS, Gibson SJ, Kedl RM, Kieper WC, Qiu X, Tomai MA, Alkan SS, Vasilakos JP: Synthetic TLR agonists reveal functional differences between human TLR7 and TLR8. J Immunol. 2005 Feb 1;174(3):1259-68. [PubMed:15661881]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:34