imiquimod 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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

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
Application site erythema 87.82 24.52 22 1667 4516 50598919
Erythema 78.92 24.52 53 1636 146361 50457074
Application site reaction 76.15 24.52 14 1675 660 50602775
Application site scab 56.26 24.52 9 1680 183 50603252
Application site ulcer 54.12 24.52 8 1681 94 50603341
Off label use 50.76 24.52 70 1619 474356 50129079
Application site erosion 49.27 24.52 8 1681 179 50603256
Influenza like illness 43.87 24.52 26 1663 57433 50546002
Skin erosion 43.58 24.52 11 1678 2320 50601115
Application site pain 42.77 24.52 12 1677 3786 50599649
Dermoid cyst 37.69 24.52 6 1683 118 50603317
Application site inflammation 37.20 24.52 7 1682 374 50603061
Scab 36.30 24.52 12 1677 6550 50596885
Application site oedema 35.91 24.52 5 1684 37 50603398
Skin reaction 33.15 24.52 13 1676 11555 50591880
Application site discharge 29.10 24.52 5 1684 159 50603276
Cutaneous lupus erythematosus 28.83 24.52 8 1681 2423 50601012
Application site irritation 27.13 24.52 7 1682 1608 50601827
Application site infection 26.54 24.52 4 1685 54 50603381
Chronic papillomatous dermatitis 26.54 24.52 4 1685 54 50603381
Oedema 25.33 24.52 20 1669 70161 50533274

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 121.30 27.21 21 1960 339 29572207
Scab 98.44 27.21 27 1954 3907 29568639
Application site erythema 94.51 27.21 23 1958 2076 29570470
Application site reaction 85.82 27.21 16 1965 398 29572148
Forced expiratory volume decreased 78.28 27.21 21 1960 2792 29569754
Erythema 77.10 27.21 53 1928 75553 29496993
Application site ulcer 70.34 27.21 9 1972 11 29572535
Pulmonary function test decreased 70.14 27.21 21 1960 4142 29568404
Application site inflammation 62.53 27.21 10 1971 96 29572450
Influenza like illness 61.99 27.21 31 1950 24439 29548107
Obstructive airways disorder 53.54 27.21 22 1959 10994 29561552
Application site scab 51.56 27.21 8 1973 62 29572484
Erythema multiforme 42.97 27.21 17 1964 7700 29564846
Skin reaction 40.34 27.21 14 1967 4403 29568143
Upper respiratory tract infection 39.70 27.21 24 1957 27325 29545221
Application site pain 39.56 27.21 11 1970 1668 29570878
Chills 37.73 27.21 34 1947 71266 29501280
Application site erosion 36.07 27.21 6 1975 75 29572471
Application site oedema 33.19 27.21 5 1976 31 29572515
Asthma 30.36 27.21 22 1959 33827 29538719
Application site irritation 28.79 27.21 7 1974 627 29571919
Application site exfoliation 27.66 27.21 5 1976 104 29572442

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
Application site erythema 175.89 24.47 42 3223 4647 64490820
Erythema 141.70 24.47 98 3167 186972 64308495
Application site reaction 138.58 24.47 25 3240 690 64494777
Application site inflammation 101.62 24.47 18 3247 446 64495021
Application site ulcer 94.43 24.47 14 3251 106 64495361
Scab 87.82 24.47 28 3237 8994 64486473
Application site scab 79.52 24.47 13 3252 196 64495271
Application site erosion 71.55 24.47 12 3253 213 64495254
Vital capacity decreased 69.42 24.47 15 3250 1057 64494410
Skin reaction 67.93 24.47 25 3240 12327 64483140
Influenza like illness 67.90 24.47 41 3224 61661 64433806
Application site oedema 67.41 24.47 10 3255 76 64495391
Off label use 59.95 24.47 111 3154 632695 63862772
Application site irritation 53.32 24.47 13 3252 1563 64493904
Application site pain 53.21 24.47 16 3249 4232 64491235
Skin erosion 50.28 24.47 15 3250 3861 64491606
Dermoid cyst 48.67 24.47 9 3256 285 64495182
Application site exfoliation 47.61 24.47 9 3256 322 64495145
Pulmonary function test decreased 42.75 24.47 15 3250 6446 64489021
Oedema 42.46 24.47 36 3229 91899 64403568
Forced expiratory volume decreased 41.85 24.47 15 3250 6852 64488615
Erythema multiforme 39.00 24.47 18 3247 15683 64479784
Application site swelling 36.09 24.47 8 3257 634 64494833
Application site dermatitis 32.79 24.47 6 3259 179 64495288
Vitiligo 32.60 24.47 9 3256 1759 64493708
Local reaction 32.46 24.47 7 3258 488 64494979
Application site necrosis 30.02 24.47 4 3261 12 64495455
Application site discharge 29.78 24.47 6 3259 300 64495167
Obstructive airways disorder 27.01 24.47 16 3249 23169 64472298
Application site scar 26.20 24.47 5 3260 188 64495279
Chills 25.47 24.47 33 3232 137231 64358236
Cutaneous lupus erythematosus 24.76 24.47 8 3257 2674 64492793
Skin plaque 24.57 24.47 11 3254 8929 64486538

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 D000276 Adjuvants, Immunologic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D007155 Immunologic Factors
MeSH PA D007369 Interferon Inducers
CHEBI has role CHEBI:35610 antineoplastic agents
CHEBI has role CHEBI:36710 interferon inducers

Drug Use (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
5% ALDARA BAUSCH N020723 Feb. 27, 1997 RX CREAM TOPICAL 7696159 April 1, 2024 TREATMENT OF BIOPSY-CONFIRMED, PRIMARY SUPERFICIAL BASAL CELL CARCINOMA (SBCC)
5% ALDARA BAUSCH N020723 Feb. 27, 1997 RX CREAM TOPICAL 7696159 April 1, 2024 WORKS THROUGH THE INDUCTION OF INTERFERON AND OTHER CYTOKINES
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

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

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 0168-0432 CREAM 50 mg TOPICAL ANDA 25 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 45802-368 CREAM 12.50 mg TOPICAL ANDA 25 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 51672-4145 CREAM 50 mg TOPICAL ANDA 28 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 51672-4174 CREAM 37.50 mg TOPICAL ANDA 28 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 52549-4145 CREAM 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 63629-8818 CREAM 37.50 mg TOPICAL NDA authorized generic 26 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 63629-8818 CREAM 37.50 mg TOPICAL NDA authorized generic 26 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 27 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
Aldara HUMAN PRESCRIPTION DRUG LABEL 1 99207-260 CREAM 50 mg TOPICAL NDA 28 sections
Aldara HUMAN PRESCRIPTION DRUG LABEL 1 99207-260 CREAM 50 mg TOPICAL NDA 28 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-270 CREAM 37.50 mg TOPICAL NDA 27 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-270 CREAM 37.50 mg TOPICAL NDA 27 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-271 CREAM 37.50 mg TOPICAL NDA 27 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-271 CREAM 37.50 mg TOPICAL NDA 27 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-276 CREAM 2.50 mg TOPICAL NDA 27 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-276 CREAM 2.50 mg TOPICAL NDA 27 sections