Scroll

imiquimod 🐶 Veterinary Use | 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
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

Molecule

Description

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:

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	88.83	24.81	22	1876	4813	63482311
Erythema	77.71	24.81	54	1844	175697	63311427
Application site reaction	76.19	24.81	14	1884	736	63486388
Application site scab	57.06	24.81	9	1889	187	63486937
Application site ulcer	54.77	24.81	8	1890	97	63487027
Application site erosion	49.82	24.81	8	1890	187	63486937
Skin erosion	48.53	24.81	12	1886	2600	63484524
Off label use	45.85	24.81	76	1822	674386	62812738
Influenza like illness	45.47	24.81	27	1871	66797	63420327
Application site inflammation	44.30	24.81	8	1890	381	63486743
Application site pain	42.93	24.81	12	1886	4170	63482954
Application site oedema	36.11	24.81	5	1893	40	63487084
Dermoid cyst	35.82	24.81	6	1892	183	63486941
Scab	35.62	24.81	12	1886	7751	63479373
Skin reaction	31.39	24.81	13	1885	14836	63472288
Application site discharge	29.27	24.81	5	1893	172	63486952
Cutaneous lupus erythematosus	28.83	24.81	8	1890	2704	63484420
Application site irritation	27.34	24.81	7	1891	1743	63485381
Application site infection	26.71	24.81	4	1894	58	63487066
Chronic papillomatous dermatitis	26.46	24.81	4	1894	62	63487062
Chronic cutaneous lupus erythematosus	25.45	24.81	5	1893	375	63486749

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
Vital capacity decreased	121.86	27.25	21	2072	371	34954467
Scab	106.18	27.25	29	2064	4625	34950213
Application site erythema	94.62	27.25	23	2070	2313	34952525
Application site reaction	87.19	27.25	16	2077	409	34954429
Forced expiratory volume decreased	77.91	27.25	21	2072	3182	34951656
Erythema	74.75	27.25	53	2040	88727	34866111
Application site ulcer	70.09	27.25	9	2084	14	34954824
Pulmonary function test decreased	68.77	27.25	21	2072	4954	34949884
Application site inflammation	63.56	27.25	10	2083	97	34954741
Influenza like illness	61.71	27.25	31	2062	27603	34927235
Application site scab	51.90	27.25	8	2085	67	34954771
Obstructive airways disorder	48.69	27.25	22	2071	15472	34939366
Erythema multiforme	42.94	27.25	17	2076	8632	34946206
Skin reaction	39.56	27.25	14	2079	5216	34949622
Application site pain	39.38	27.25	11	2082	1897	34952941
Chills	39.23	27.25	35	2058	81008	34873830
Upper respiratory tract infection	37.98	27.25	24	2069	33035	34921803
Application site erosion	34.90	27.25	6	2087	104	34954734
Application site oedema	33.75	27.25	5	2088	31	34954807
Asthma	30.21	27.25	23	2070	42633	34912205
Application site irritation	28.93	27.25	7	2086	688	34954150

FDA Adverse Event Reporting System (Geriatric)

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	177.13	22.30	42	3552	5068	79735726
Application site reaction	139.42	22.30	25	3569	751	79740043
Erythema	136.21	22.30	98	3496	223192	79517602
Application site inflammation	110.09	22.30	19	3575	455	79740339
Scab	94.88	22.30	30	3564	10542	79730252
Application site ulcer	94.83	22.30	14	3580	117	79740677
Application site scab	80.30	22.30	13	3581	208	79740586
Application site erosion	70.07	22.30	12	3582	274	79740520
Influenza like illness	69.16	22.30	42	3552	71665	79669129
Application site oedema	68.12	22.30	10	3584	80	79740714
Skin reaction	64.35	22.30	25	3569	16043	79724751
Vital capacity decreased	63.28	22.30	15	3579	1801	79738993
Skin erosion	54.32	22.30	16	3578	4429	79736365
Application site irritation	53.51	22.30	13	3581	1731	79739063
Application site pain	53.28	22.30	16	3578	4731	79736063
Off label use	50.98	22.30	120	3474	907095	78833699
Dermoid cyst	49.18	22.30	9	3585	303	79740491
Erythema multiforme	45.34	22.30	20	3574	17631	79723163
Application site exfoliation	44.32	22.30	9	3585	527	79740267
Pulmonary function test decreased	41.99	22.30	15	3579	7622	79733172
Forced expiratory volume decreased	41.66	22.30	15	3579	7799	79732995
Oedema	37.89	22.30	36	3558	119544	79621250
Application site swelling	35.74	22.30	8	3586	745	79740049
Chronic cutaneous lupus erythematosus	33.57	22.30	7	3587	467	79740327
Application site dermatitis	33.20	22.30	6	3588	188	79740606
Vitiligo	32.06	22.30	9	3585	2100	79738694
Local reaction	31.85	22.30	7	3587	600	79740194
Application site necrosis	29.60	22.30	4	3590	16	79740778
Application site discharge	29.52	22.30	6	3588	353	79740441
Chills	27.57	22.30	35	3559	160199	79580595
Pathogen resistance	26.69	22.30	13	3581	14329	79726465
Application site scar	26.68	22.30	5	3589	192	79740602
Cutaneous lupus erythematosus	24.78	22.30	8	3586	2995	79737799
Obstructive airways disorder	24.22	22.30	16	3578	31443	79709351
Immune reconstitution inflammatory syndrome	24.12	22.30	12	3582	13829	79726965
Chronic papillomatous dermatitis	24.05	22.30	4	3590	76	79740718
Skin plaque	23.85	22.30	11	3583	10734	79730060
Application site infection	23.32	22.30	4	3590	92	79740702
Skin ulcer	22.47	22.30	19	3575	54131	79686663

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
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 | Suggest Off label Use Form| |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

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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	DISCN	CREAM	TOPICAL	7696159	April 1, 2024	TREATMENT OF BIOPSY-CONFIRMED, PRIMARY SUPERFICIAL BASAL CELL CARCINOMA (SBCC)
5%	ALDARA	BAUSCH	N020723	Feb. 27, 1997	DISCN	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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Toll-like receptor 7	Membrane receptor	Q9NYK1	TLR7_HUMAN	AGONIST	EC50	4.97	CHEMBL	CHEMBL
Adenosine receptor A2a	GPCR	P29274	AA2AR_HUMAN		Ki	5.53	DRUG MATRIX
Histamine H2 receptor	GPCR	P25021	HRH2_HUMAN		Ki	5.83	DRUG MATRIX
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN		Ki	5.89	DRUG MATRIX
7,8-dihydro-8-oxoguanine triphosphatase	Enzyme	P36639	8ODP_HUMAN		IC50	6.19	CHEMBL

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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	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