imiquimod 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 110.11 42.22 19 275 1261 2356530
Erythema 90.54 42.22 28 266 25131 2332660
Application site reaction 72.06 42.22 11 283 332 2357459
Application site scab 69.89 42.22 9 285 74 2357717
Influenza like illness 67.58 42.22 19 275 12095 2345696
Skin erosion 62.56 42.22 10 284 408 2357383
Scab 58.78 42.22 11 283 1137 2356654
Skin reaction 52.71 42.22 11 283 1986 2355805
Application site erosion 52.49 42.22 7 287 77 2357714
Off label use 51.85 42.22 25 269 73573 2284218
Dermoid cyst 47.41 42.22 6 288 42 2357749
Pyrexia 46.24 42.22 21 273 53687 2304104
Application site discharge 44.35 42.22 6 288 74 2357717
Application site pain 43.71 42.22 9 285 1517 2356274

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
Application site erythema 137.54 41.31 23 338 611 1745809
Scab 113.58 41.31 20 341 722 1745698
Application site reaction 100.79 41.31 15 346 180 1746240
Influenza like illness 90.60 41.31 24 337 6029 1740391
Application site ulcer 73.27 41.31 9 352 19 1746401
Erythema 70.42 41.31 24 337 14164 1732256
Chills 66.80 41.31 22 339 11665 1734755
Application site inflammation 66.26 41.31 9 352 52 1746368
Application site scab 66.11 41.31 9 352 53 1746367
Erythema multiforme 62.45 41.31 14 347 1732 1744688
Molluscum contagiosum 53.01 41.31 8 353 105 1746315
Application site pain 49.94 41.31 10 351 716 1745704
Inflammation 48.22 41.31 13 348 3437 1742983
Asthenia 46.62 41.31 23 338 34647 1711773
Myalgia 45.88 41.31 18 343 15640 1730780
Treatment failure 45.08 41.31 13 348 4388 1742032

Pharmacologic Action:

SourceCodeDescription
ATC D06BB10 DERMATOLOGICALS
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
CHEMOTHERAPEUTICS FOR TOPICAL USE
Antivirals
MeSH PA D000276 Adjuvants, Immunologic
FDA PE N0000009267 Increased Cytokine Activity
FDA PE N0000009269 Increased Cytokine Production
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:36710 interferon inducer
MeSH PA D000970 Antineoplastic Agents
MeSH PA D007155 Immunologic Factors
MeSH PA D007369 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

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 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

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 5.52 DRUG MATRIX
Histamine H2 receptor GPCR Ki 5.83 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 5.89 DRUG MATRIX

External reference:

IDSource
D000077271 MESH_DESCRIPTOR_UI
4021044 VUID
N0000148508 NUI
C0165032 UMLSCUI
D02500 KEGG_DRUG
108939005 SNOMEDCT_US
171571 MMSL
006479 NDDF
4872 MMSL
59943 RXNORM
386941002 SNOMEDCT_US
4021044 VANDF
57469 PUBCHEM_CID
CHEBI:36704 CHEBI
CHEMBL1282 ChEMBL_ID
DB00724 DRUGBANK_ID
P1QW714R7M UNII
6911 INN_ID
5003 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 0168-0432 CREAM 50 mg TOPICAL ANDA 16 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 45802-368 CREAM 12.50 mg TOPICAL ANDA 15 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 51672-4145 CREAM 50 mg TOPICAL ANDA 17 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 52549-4145 CREAM 50 mg TOPICAL ANDA 17 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 54868-6179 CREAM 50 mg TOPICAL ANDA 16 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 68462-536 CREAM 50 mg TOPICAL ANDA 17 sections
Imiquimod HUMAN PRESCRIPTION DRUG LABEL 1 68682-272 CREAM 37.50 mg TOPICAL NDA 16 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 16 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-270 CREAM 37.50 mg TOPICAL NDA 16 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-271 CREAM 37.50 mg TOPICAL NDA 16 sections
Zyclara HUMAN PRESCRIPTION DRUG LABEL 1 99207-276 CREAM 2.50 mg TOPICAL NDA 16 sections