imiquimod Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| immunomodulators, both stimulant/suppressive and stimulant | 1429 | 99011-02-6 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
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.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
None
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| 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:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Sept. 18, 1998 | EMA | ||
| Feb. 27, 1997 | FDA | MEDICIS |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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 term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients 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:
| Source | Code | Description |
|---|---|---|
| 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)
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| 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 level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 7.12 | Basic |
| pKa2 | 5.99 | Basic |
Orange Book patent data (new drug applications)
| Formulation strength | Trade name | Applicant | Application number | Approval date | Type | Dose form | Route | Patent number | Patent expiration date | Patent 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:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA 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:
| ID | Source |
|---|---|
| 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:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| 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 |