imiquimod 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
immunomodulators, both stimulant/suppressive and stimulant 1429 99011-02-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • imiquimod
  • aldara
  • beselna
  • zyclara
A topically-applied aminoquinoline immune modulator that induces interferon production. It is used in the treatment of external genital and perianal warts, superficial CARCINOMA, BASAL CELL; and ACTINIC KERATOSIS.
  • Molecular weight: 240.31
  • Formula: C14H16N4
  • CLOGP: 3.24
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 56.73
  • ALOGS: -2.99
  • ROTB: 2
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.60 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1 % Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 47 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 2.378 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.701 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 36.392 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 34.435 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 29.040 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 47.180 % High 1
herg hERG pIC50 5.226 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 11.668 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 28.054 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 17.450 % High 1
kinase-safety-class ACVR2A,ACVR2B,AXL,BRAF,CAMK2B,CAMK2D,CDK9,DYRK1B,EGFR,EIF2AK3,ERBB2,FLT3,GRK2,ITK,MAP3K10,MAP3K21,MAPK7,PDK2,PIK3CA,PIK3CD,PRKDC,SIK2,SIK3,ULK1 24
kinase-selectivity-class ACVR2A,ACVR2B,AXL,CAMK2D,CDK9,DYRK1B,MAP3K21,MET,SIK2,SIK3 10
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.795 High 1
mh-clint Mouse hepatocyte intrinsic clearance 111.173 High 1
mppb Mouse plasma protein binding (% unbound) 25.880 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 2.911 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 35.460 % High 1
rh-clint Rat hepatocyte intrinsic clearance 143.549 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 77.010 % High 1
rppb Rat plasma protein binding (% unbound) 28.050 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 287.740 uM High 1

Approvals:

DateAgencyCompanyOrphan
Sept. 18, 1998 EMA
Feb. 27, 1997 FDA MEDICIS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Skin irritation 107.69 26.53 29 1735 13574 90613109
Skin ulcer 74.02 26.53 30 1734 50045 90576638
Erythema 73.45 26.53 49 1715 229197 90397486
Off label use 54.65 26.53 85 1679 1102167 89524516
Application site erythema 45.43 26.53 12 1752 5196 90621487
Application site scab 38.36 26.53 6 1758 184 90626499
Skin erosion 35.35 26.53 9 1755 3373 90623310
Application site ulcer 34.47 26.53 5 1759 91 90626592
Application site inflammation 34.15 26.53 6 1758 378 90626305
Dermoid cyst 32.47 26.53 6 1758 502 90626181
Skin reaction 30.44 26.53 12 1752 18541 90608142
Application site reaction 29.53 26.53 6 1758 824 90625859
Chronic papillomatous dermatitis 28.50 26.53 4 1760 57 90626626

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Vital capacity decreased 122.87 30.88 21 1824 496 42618994
Scab 90.11 30.88 25 1820 5853 42613637
Erythema 85.58 30.88 55 1790 108738 42510752
Pulmonary function test decreased 72.57 30.88 21 1824 5711 42613779
Forced expiratory volume decreased 66.65 30.88 21 1824 7609 42611881
Application site scab 46.84 30.88 7 1838 67 42619423
Obstructive airways disorder 45.67 30.88 22 1823 24737 42594753
Skin reaction 43.75 30.88 15 1830 7052 42612438
Pathogen resistance 43.67 30.88 17 1828 11433 42608057
Influenza like illness 43.24 30.88 23 1822 31817 42587673
Upper respiratory tract infection 37.22 30.88 23 1822 42150 42577340

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Erythema 147.43 23.57 97 3181 291350 110294671
Scab 79.35 23.57 25 3253 13211 110572810
Off label use 73.65 23.57 146 3132 1500039 109085982
Skin reaction 71.58 23.57 26 3252 21118 110564903
Application site erythema 71.25 23.57 19 3259 5591 110580430
Vital capacity decreased 67.56 23.57 15 3263 2058 110583963
Application site inflammation 55.96 23.57 10 3268 452 110585569
Application site scab 55.69 23.57 9 3269 221 110585800
Pathogen resistance 49.81 23.57 19 3259 17653 110568368
Dermoid cyst 48.69 23.57 9 3269 492 110585529
Skin erosion 47.67 23.57 14 3264 5840 110580181
Pulmonary function test decreased 46.24 23.57 15 3263 8685 110577336
Influenza like illness 45.87 23.57 30 3248 88382 110497639
Application site reaction 43.97 23.57 9 3269 838 110585183
Drug resistance 41.70 23.57 24 3254 56350 110529671
Forced expiratory volume decreased 40.15 23.57 15 3263 13161 110572860
Application site erosion 38.66 23.57 7 3271 341 110585680
Application site ulcer 38.30 23.57 6 3272 120 110585901
Oedema 37.13 23.57 38 3240 209938 110376083
Application site irritation 36.56 23.57 9 3269 1928 110584093
Skin irritation 33.63 23.57 14 3264 16305 110569716
Local reaction 32.92 23.57 7 3271 785 110585236
Application site swelling 32.13 23.57 7 3271 880 110585141
Chronic cutaneous lupus erythematosus 31.16 23.57 7 3271 1012 110585009
Skin ulcer 29.16 23.57 20 3258 63625 110522396
Application site scar 28.93 23.57 5 3273 186 110585835
Chills 27.53 23.57 31 3247 190549 110395472
Immune reconstitution inflammatory syndrome 27.10 23.57 12 3266 16214 110569807
Skin plaque 26.56 23.57 11 3267 12634 110573387
Papilloma viral infection 26.00 23.57 7 3271 2131 110583890
Squamous cell carcinoma 25.62 23.57 12 3266 18451 110567570
Chronic papillomatous dermatitis 25.30 23.57 4 3274 85 110585936
Obstructive airways disorder 24.75 23.57 16 3262 46133 110539888

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC D06BB10 DERMATOLOGICALS
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
CHEMOTHERAPEUTICS FOR TOPICAL USE
Antivirals
FDA MoA N0000000157 Interferon Inducers
FDA PE N0000009267 Increased Cytokine Activity
FDA PE N0000009269 Increased Cytokine Production
MeSH PA D000097912 Toll-Like Receptor Agonists
MeSH PA D000276 Adjuvants, Immunologic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D007155 Immunologic Factors
MeSH PA D007369 Interferon Inducers
CHEBI has role CHEBI:22587 antiviral agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:36710 interferon inducer
CHEBI has role CHEBI:38068 antimalarial
CHEBI has role CHEBI:62868 hepatoprotective agent
CHEBI has role CHEBI:64951 anti-HBV agent
CHEBI has role CHEBI:70868 antileishmanial agent

Related Drugs by ATC class:

D06BB Antivirals 11 drugs
acyclovirberdazimerdocosanoledoxudineibacitabineidoxuridineinosinepenciclovirpodophyllotoxinsinecatechinstromantadine

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Verruca indication 30285000
Actinic keratosis indication 201101007 DOID:8866
Condyloma acuminatum indication 240542006 DOID:11168
Superficial basal cell carcinoma indication 403914000
Neoplasm of vulva off-label use 126922007 DOID:1245
Sunburn contraindication 23346002
Immunosuppression contraindication 38013005
Autoimmune disease contraindication 85828009
Photosensitivity contraindication 90128006
Graft-versus-host disease contraindication 234646005




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.12 Basic
pKa2 5.99 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 10238645 Aug. 18, 2029 TREATMENT OF GENITAL WARTS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 10238645 Aug. 18, 2029 TREATMENT OF PERIANAL WARTS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 8598196 Aug. 18, 2029 TREATMENT OF GENITAL WARTS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 8598196 Aug. 18, 2029 TREATMENT OF PERIANAL WARTS
2.5% ZYCLARA BAUSCH N022483 July 15, 2011 RX CREAM TOPICAL 11318130 Dec. 11, 2029 TREATMENT OF ACTINIC KERATOSIS
2.5% ZYCLARA BAUSCH N022483 July 15, 2011 RX CREAM TOPICAL 8222270 Dec. 11, 2029 TREATMENT OF ACTINIC KERATOSIS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 10238644 Dec. 11, 2029 TREATMENT OF ACTINIC KERATOSIS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 8236816 Dec. 11, 2029 TREATMENT OF ACTINIC KERATOSIS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 8299109 Dec. 11, 2029 TREATMENT OF ACTINIC KERATOSIS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 10918635 April 30, 2030 TREATMENT OF GENITAL WARTS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 10918635 April 30, 2030 TREATMENT OF PERIANAL WARTS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 11202752 April 30, 2030 TREATMENT OF GENITAL WARTS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 11202752 April 30, 2030 TREATMENT OF PERIANAL WARTS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 11850245 April 30, 2030 TREATMENT OF GENITAL WARTS
3.75% ZYCLARA BAUSCH N022483 March 25, 2010 RX CREAM TOPICAL 11850245 April 30, 2030 TREATMENT OF PERIANAL WARTS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Toll-like receptor 7 Membrane receptor AGONIST EC50 4.97 CHEMBL CHEMBL
Adenosine receptor A2a GPCR Ki 5.53 DRUG MATRIX
Histamine H2 receptor GPCR Ki 5.83 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 5.89 DRUG MATRIX
7,8-dihydro-8-oxoguanine triphosphatase Enzyme IC50 6.19 CHEMBL

External reference:

IDSource
4021044 VUID
N0000148508 NUI
D02500 KEGG_DRUG
4021044 VANDF
C0165032 UMLSCUI
CHEBI:36704 CHEBI
6T0 PDB_CHEM_ID
CHEMBL1282 ChEMBL_ID
DB00724 DRUGBANK_ID
D000077271 MESH_DESCRIPTOR_UI
57469 PUBCHEM_CID
5003 IUPHAR_LIGAND_ID
6911 INN_ID
P1QW714R7M UNII
215085 RXNORM
171571 MMSL
171678 MMSL
187724 MMSL
4872 MMSL
9862 MMSL
006479 NDDF
108939005 SNOMEDCT_US
386941002 SNOMEDCT_US
P1QW714R7M INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 0093-3133 CREAM 37.50 mg TOPICAL NDA authorized generic 27 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 45802-368 CREAM 12.50 mg TOPICAL ANDA 26 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 51672-4145 CREAM 50 mg TOPICAL ANDA 29 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 51672-4174 CREAM 37.50 mg TOPICAL ANDA 27 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 54868-6179 CREAM 50 mg TOPICAL ANDA 25 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 68462-536 CREAM 50 mg TOPICAL ANDA 25 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 68682-272 CREAM 37.50 mg TOPICAL NDA 25 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 71335-2725 CREAM 12.50 mg TOPICAL ANDA 26 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 71335-3000 CREAM 12.50 mg TOPICAL ANDA 26 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 72162-2332 CREAM 12.50 mg TOPICAL ANDA 26 sections
IMIQUIMOD HUMAN PRESCRIPTION DRUG LABEL 1 72189-084 CREAM 12.50 mg TOPICAL ANDA 13 sections
IMIQUIMOD 5% / LEVOCETIRIZINE DIHYDROCHLORIDE 1% / NIACINAMIDE 2% HUMAN PRESCRIPTION DRUG LABEL 3 72934-1125 GEL 5 g TOPICAL unapproved drug other 4 sections
IMIQUIMOD 5% / LEVOCETIRIZINE DIHYDROCHLORIDE 1% / TRETINOIN 0.05% HUMAN PRESCRIPTION DRUG LABEL 3 72934-1126 GEL 5 g TOPICAL unapproved drug other 4 sections
IMIQUIMOD 5% / NIACINAMIDE 4% HUMAN PRESCRIPTION DRUG LABEL 2 72934-1127 GEL 5 g TOPICAL unapproved drug other 4 sections
IMIQUIMOD 5% / SALICYLIC ACID 30% / TRETINOIN 0.1% HUMAN PRESCRIPTION DRUG LABEL 3 72934-1128 GEL 5 g TOPICAL unapproved drug other 4 sections
IMIQUIMOD 5% / TRETINOIN 0.025% HUMAN PRESCRIPTION DRUG LABEL 2 72934-1129 GEL 5 g TOPICAL unapproved drug other 4 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-270 CREAM 37.50 mg TOPICAL NDA 25 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-271 CREAM 37.50 mg TOPICAL NDA 25 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-276 CREAM 2.50 mg TOPICAL NDA 25 sections