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/1000mgTopicalPhysicians Total Care, Inc.2003-06-192009-09-30Us
AldaraCream50 mg/1gTopicalValeant Pharmaceuticals North America1997-02-27Not applicableUs
AldaraCream50 mg/1000mgTopical3 M Pharmaceuticals2011-06-242015-01-31Us
AldaraCream50 mg/1000mgTopicalGraceway Pharmaceuticals2011-06-242015-01-31Us
Aldara PCream5 %TopicalValeant Canada Lp Valeant Canada S.E.C.1999-07-05Not applicableCanada
ImiquimodCream50 mg/1000mgTopicalPerrigo New York Inc.2010-04-202013-08-01Us
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
ZyclaraCream3.75 %TopicalValeant Canada Lp Valeant Canada S.E.C.2010-01-27Not applicableCanada
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/1gTopicalSandoz2011-02-282014-05-31Us
ImiquimodCream50 mg/1gTopicalImpax Generics2011-02-282017-06-01Us
ImiquimodCream50 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2011-04-15Not applicableUs
ImiquimodCream50 mg/1gTopicalTeva2013-12-192015-04-30Us
ImiquimodCream50 mg/1gTopicalTaro Pharmaceutical Industries, Ltd.2011-04-15Not applicableUs
ImiquimodCream50 mg/1000mgTopicalApotex Corporation2012-09-14Not applicableUs
ImiquimodCream50 mg/1gTopicalStrides Shasun Limited2014-06-24Not applicableUs
ImiquimodCream12.5 mg/0.25gTopicalPerrigo New York Inc.2010-11-09Not applicableUs
ImiquimodCream50 mg/1gTopicalPhysicians Total Care, Inc.2010-09-22Not applicableUs
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.

Associated Conditions
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
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Imiquimod.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Imiquimod.
16-BromoepiandrosteroneThe metabolism of 16-Bromoepiandrosterone can be decreased when combined with Imiquimod.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when Imiquimod is combined with 2-Methoxyethanol.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Imiquimod.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Imiquimod.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Imiquimod.
6-Deoxyerythronolide BThe metabolism of Imiquimod can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Imiquimod.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when Imiquimod is combined with 9-(N-methyl-L-isoleucine)-cyclosporin A.
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
HMDB0014862
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
0Active Not RecruitingTreatmentHigh Risk WHO Grade II Glioma / Recurrent/Post-Chemotherapy WHO Grade II Glioma1
0RecruitingTreatmentLymphoma, T-Cell, Cutaneous1
0RecruitingTreatmentMetastatic Melanoma / Stage IIIB Cutaneous Melanoma AJCC v7 / Stage IIIC Cutaneous Melanoma AJCC v7 / Stage IV Cutaneous Melanoma AJCC v6 and v71
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentActinic Keratosis (AK)1
1CompletedTreatmentAdenocarcinoma of the Prostate1
1CompletedTreatmentAnaplastic Astrocytoma (AA) / Ependymomas / Glioblastomas / Medulloblastomas / Neoplasms, Brain1
1CompletedTreatmentCervical Intraepithelial Neoplasia (CIN 2/3) / HPV16 Positive / HPV16+1
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
1RecruitingPreventionInfluenza immunisation / Influenza, Avian1
1RecruitingTreatmentCancer, Breast / Malignant Neoplasm of Stomach1
1RecruitingTreatmentCervical Cancers / HPV Disease / Human Papilomavirus / Precancerous Conditions1
1RecruitingTreatmentSarcoma, Bone / Sarcomas / Soft Tissue Sarcoma (STS)1
1RecruitingTreatmentSquamous Cell Carcinoma (SCC)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 RecruitingTreatmentCancers / Progressive Solid Malignancies / Refractory Solid Malignancies1
1, 2Active Not RecruitingTreatmentRecurrent Prostate Cancer1
1, 2CompletedTreatmentCarcinoma, Colorectal1
1, 2RecruitingTreatmentPrimary/Relapsed Acute Lymphoblastic Leukemia (ALL) of Childhood, Adolescents and Young Adults1
2Active Not RecruitingTreatmentCancer of the Ovary / Fallopian Tube Cancer / Primary Peritoneal 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
2CompletedTreatmentMale Breast Cancer / Metastases to skin / Recurrent Breast Cancer / Stage IV Breast Cancer1
2CompletedTreatmentMalignant Melanoma1
2Not Yet RecruitingTreatmentBasal Cell Carcinoma (BCC) / Basal Cell Carcinoma of Skin, Site Unspecified / Invasive Carcinoma / Skin Cancers1
2RecruitingTreatmentCervical Dysplasia / Cervical Intraepithelial Neoplasia (CIN)1
2RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL)1
2RecruitingTreatmentHuman Papillomavirus (HPV) / Neoplasms, Vulvar / Pre-cancerous Lesions of the Vulva / VIN2 / VIN3 / Vulvar Dysplasia / Vulvar High Grade Squamous Intraepithelial Lesion (HSIL) / Vulvar Intraepithelial Neoplasia (VIN)1
2RecruitingTreatmentUterine Cervical Neoplasm1
2TerminatedPreventionChronic Lymphocytic Leukaemia (CLL)1
2TerminatedTreatmentPort Wine Stains1
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
3Active Not RecruitingTreatmentNodular Basal Cell Carcinoma1
3Active Not RecruitingTreatmentPaget Disease, Extramammary1
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
3Not Yet RecruitingTreatmentAnogenital Human Papillomavirus Infection / Condyloma Anal1
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
3RecruitingTreatmentCervical Intraepithelial Neoplasia (CIN)1
3RecruitingTreatmentHutchinson's Melanotic Freckle1
3RecruitingTreatmentLentigo Maligna Melanoma (Head or Neck)1
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 RecruitingTreatmentCervical Intraepithelial Neoplasia (CIN)1
Not AvailableCompletedNot AvailableActinic Keratosis (AK)1
Not AvailableCompletedPreventionIllness, Chronic1
Not AvailableCompletedTreatmentActinic Keratosis (AK)1
Not AvailableCompletedTreatmentCancers / Hutchinson's Melanotic Freckle1
Not AvailableCompletedTreatmentPort Wine Stains1
Not AvailableCompletedTreatmentSolar Elastosis1
Not AvailableCompletedTreatmentVulvar Cancers1
Not AvailableNot Yet RecruitingTreatmentMycosis Fungoides (MF)1
Not AvailableRecruitingBasic ScienceNormal Skin / Photoaged Skin1
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
  • 3M Health Care
  • Dispensing Solutions
  • E. Fougera and Co.
  • Graceway Pharmaceuticals
Dosage forms
FormRouteStrength
CreamTopical50 mg/1000mg
CreamTopical5 %
CreamTopical12.5 mg/0.25g
CreamTopical50 mg/1g
CreamTopical50 mg
CreamTopical3.75 %
CreamTopical2.5 %
CreamTopical2.5 mg/1g
CreamTopical2.5 mg/100mg
CreamTopical3.75 mg/100mg
CreamTopical37.5 mg/1g
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
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 October 16, 2018 08:30