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

Stem definitionDrug idCAS RN
systemic antifungal agents, miconazole derivatives 983 27220-47-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • econazole
  • econazole nitrate
  • ecostatin
  • micofugal
An imidazole derivative that is commonly used as a topical antifungal agent.
  • Molecular weight: 381.68
  • Formula: C18H15Cl3N2O
  • CLOGP: 5.10
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 0
  • TPSA: 27.05
  • ALOGS: -5.41
  • ROTB: 6
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.10 g V

ADMET properties:

PropertyValueReference
S (Water solubility) 0.00 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Bocci G, Oprea TI, Benet LZ

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 4.869 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.799 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 15.885 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 28.907 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 0.190 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 0.590 % High 1
herg hERG pIC50 5.777 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 14.757 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 46.026 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 0.380 % High 1
kinase-safety-class ACVR2A,ACVR2B,AKT2,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,GRK2,GSK3B,JAK2,MAP3K7,MAPK12,MAPK7,MAPK9,NTRK2,PDK2,PDK4,PDPK1,PIK3CB,PIK3CG,PIM2,PRKDC,SIK2,SIK3,STK33,TEK,TTK 35
kinase-selectivity-class AKT2,AKT3,AXL,EIF2AK3,GRK2,PDK4 6
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.392 High 1
mh-clint Mouse hepatocyte intrinsic clearance 40.551 High 1
mppb Mouse plasma protein binding (% unbound) 0.280 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.164 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 0.690 % High 1
rh-clint Rat hepatocyte intrinsic clearance 53.211 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 3.020 % High 1
rppb Rat plasma protein binding (% unbound) 0.240 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 30.620 uM High 1

Approvals:

DateAgencyCompanyOrphan
Dec. 23, 1982 FDA

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
Acute generalised exanthematous pustulosis 136.04 27.28 39 2913 13664 90611831
Acute motor-sensory axonal neuropathy 98.90 27.28 16 2936 359 90625136
Rash maculo-papular 94.24 27.28 39 2913 40894 90584601
Angiodermatitis 86.15 27.28 13 2939 182 90625313
International normalised ratio increased 66.76 27.28 32 2920 47284 90578211
Eosinophilia 61.65 27.28 26 2926 28507 90596988
Dermatitis exfoliative generalised 51.38 27.28 15 2937 5578 90619917
Drug reaction with eosinophilia and systemic symptoms 48.68 27.28 25 2927 42733 90582762
Purpura 47.72 27.28 18 2934 14760 90610735
Tarsal tunnel syndrome 46.58 27.28 9 2943 568 90624927
Purpura senile 46.00 27.28 9 2943 606 90624889
Lip oedema 45.09 27.28 13 2939 4626 90620869
Hypothalamic pituitary adrenal axis suppression 44.73 27.28 8 2944 330 90625165
Oedema mouth 43.58 27.28 11 2941 2375 90623120
Drug interaction 43.29 27.28 49 2903 276404 90349091
Gastrointestinal ulcer haemorrhage 42.21 27.28 9 2943 929 90624566
Granulomatous liver disease 42.11 27.28 9 2943 940 90624555
Resorption bone increased 39.87 27.28 9 2943 1210 90624285
Vestibular disorder 37.72 27.28 9 2943 1540 90623955
Pyelonephritis 31.82 27.28 15 2937 21301 90604194
Folate deficiency 31.34 27.28 9 2943 3156 90622339
Renal failure 30.95 27.28 29 2923 130978 90494517
Rash pustular 30.39 27.28 11 2941 8038 90617457
Hepatitis cholestatic 29.72 27.28 11 2941 8550 90616945
Rash scarlatiniform 27.89 27.28 5 2947 209 90625286

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
Procedural haemorrhage 43.35 24.92 11 1183 2830 42617311
Pulmonary haemorrhage 28.30 24.92 11 1183 11386 42608755
Essential tremor 26.85 24.92 6 1188 897 42619244
Toxic skin eruption 26.32 24.92 11 1183 13719 42606422
Rash maculo-papular 26.01 24.92 15 1179 37488 42582653

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
Acute generalised exanthematous pustulosis 145.84 22.87 46 3661 21618 110563974
Rash maculo-papular 115.03 22.87 54 3653 74168 110511424
Acute motor-sensory axonal neuropathy 92.66 22.87 16 3691 522 110585070
Angiodermatitis 85.38 22.87 13 3694 188 110585404
International normalised ratio increased 70.59 22.87 41 3666 86731 110498861
Eosinophilia 62.55 22.87 33 3674 57903 110527689
Drug reaction with eosinophilia and systemic symptoms 62.06 22.87 37 3670 82058 110503534
Purpura 51.31 22.87 22 3685 24366 110561226
Tarsal tunnel syndrome 46.76 22.87 9 3698 540 110585052
Purpura senile 45.74 22.87 9 3698 606 110584986
Dermatitis exfoliative generalised 41.02 22.87 15 3692 10957 110574635
Toxic skin eruption 39.45 22.87 19 3688 27496 110558096
Hypothalamic pituitary adrenal axis suppression 38.89 22.87 8 3699 674 110584918
Resorption bone increased 37.55 22.87 9 3698 1525 110584067
Gastrointestinal ulcer haemorrhage 36.90 22.87 9 3698 1641 110583951
Oedema mouth 35.69 22.87 10 3697 3120 110582472
Lip oedema 34.50 22.87 12 3695 7588 110578004
Procedural haemorrhage 34.32 22.87 11 3696 5416 110580176
Drug interaction 33.52 22.87 60 3647 500123 110085469
Rash papular 33.42 22.87 17 3690 27622 110557970
Vestibular disorder 32.73 22.87 9 3698 2623 110582969
Granulomatous liver disease 32.18 22.87 8 3699 1576 110584016
Pyelonephritis 31.91 22.87 16 3691 25234 110560358
Rash pustular 28.39 22.87 12 3695 12817 110572775
Folate deficiency 28.08 22.87 9 3698 4429 110581163
Renal failure 26.17 22.87 35 3672 226539 110359053
Status epilepticus 25.86 22.87 15 3692 31556 110554036
Rash scarlatiniform 25.04 22.87 5 3702 363 110585229
Vertigo positional 24.96 22.87 8 3699 3940 110581652
Skin ulcer 24.72 22.87 19 3688 63626 110521966
Cholestasis 24.49 22.87 19 3688 64499 110521093

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC D01AC03 DERMATOLOGICALS
ANTIFUNGALS FOR DERMATOLOGICAL USE
ANTIFUNGALS FOR TOPICAL USE
Imidazole and triazole derivatives
ATC G01AF05 GENITO URINARY SYSTEM AND SEX HORMONES
GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
Imidazole derivatives
ATC G01AF55 GENITO URINARY SYSTEM AND SEX HORMONES
GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
Imidazole derivatives
FDA CS M0002083 Azoles
FDA EPC N0000175487 Azole Antifungal
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000935 Antifungal Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D006727 Hormone Antagonists
MeSH PA D058888 14-alpha Demethylase Inhibitors
MeSH PA D065088 Steroid Synthesis Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors

Related Drugs by ATC class:

D01AC Imidazole and triazole derivatives 20 drugs
bifonazolechlormidazoleclotrimazoleeberconazoleefinaconazolefenticonazolefluconazoleflutrimazoleisoconazoleketoconazolelanoconazoleluliconazole show all 20 →
G01AF Imidazole derivatives 16 drugs
azanidazolebutoconazoleclotrimazolefenticonazoleflutrimazoleisoconazoleketoconazolemetronidazolemiconazoleomoconazoleornidazoleoxiconazole show all 16 →

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

DiseaseRelationSNOMED_IDDOID
Tinea pedis indication 6020002 DOID:12403
Candidiasis of skin indication 49883006
Pityriasis versicolor indication 56454009 DOID:9060
Tinea corporis indication 84849002
Tinea cruris indication 399029005
Paronychia off-label use 71906005 DOID:13117




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 6.49 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Cannabinoid receptor 1 GPCR Ki 4.54 DRUG MATRIX
Mu-type opioid receptor GPCR Ki 5.64 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 5.34 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 5.37 DRUG MATRIX
Adenosine receptor A2a GPCR Ki 5.09 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 5.79 DRUG MATRIX
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 5.05 DRUG MATRIX
Cytochrome P450 3A4 Enzyme IC50 7.30 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 6.65 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.62 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 5.03 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 5.94 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 5.36 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 5.20 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 5.30 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 5.57 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 5.79 DRUG MATRIX
Histamine H2 receptor GPCR Ki 5.81 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 6.20 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 5.94 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 6.42 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.53 DRUG MATRIX
Beta-3 adrenergic receptor GPCR Ki 5.34 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 6.18 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 6.40 DRUG MATRIX
Adenosine receptor A1 GPCR Ki 5.01 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.74 DRUG MATRIX
D(4) dopamine receptor GPCR Ki 5.49 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 5.36 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 5.46 DRUG MATRIX
Delta-type opioid receptor GPCR Ki 6.29 DRUG MATRIX
Acetylcholinesterase Enzyme IC50 4.86 DRUG MATRIX
Cytochrome P450 2C9 Enzyme IC50 6.70 DRUG MATRIX
Cytochrome P450 1A2 Enzyme IC50 6.52 DRUG MATRIX
Epidermal growth factor receptor Kinase IC50 4.49 DRUG MATRIX
Substance-P receptor GPCR Ki 5.19 DRUG MATRIX
Steroid 17-alpha-hydroxylase/17,20 lyase Enzyme Ki 6.49 CHEMBL
Cytochrome P450 2C19 Enzyme IC50 7.40 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 4.92 DRUG MATRIX
Receptor tyrosine-protein kinase erbB-2 Kinase IC50 4.86 DRUG MATRIX
Thromboxane-A synthase Enzyme IC50 7.54 DRUG MATRIX
Lanosterol 14-alpha demethylase Enzyme IC50 7.30 CHEMBL
Matrix metalloproteinase-9 Enzyme IC50 5.16 DRUG MATRIX
Indoleamine 2,3-dioxygenase 1 Enzyme IC50 5.09 CHEMBL
Substance-K receptor GPCR Ki 5.70 DRUG MATRIX
Transient receptor potential cation channel subfamily M member 2 Ion channel IC50 5.52 CHEMBL
Melanocortin receptor 5 GPCR Ki 4.43 DRUG MATRIX
Melanocortin receptor 3 GPCR Ki 4.50 DRUG MATRIX
Neuropeptide Y receptor type 2 GPCR Ki 4.96 DRUG MATRIX
Transient receptor potential cation channel subfamily M member 8 Ion channel IC50 6.38 CHEMBL
Malate dehydrogenase cytoplasmic Enzyme IC50 4.60 CHEMBL
Calcium release-activated calcium channel protein 1 Ion channel IC50 4.77 CHEMBL
Beta-1 adrenergic receptor GPCR Ki 5.13 DRUG MATRIX
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase Enzyme IC50 6.51 CHEMBL
Lanosterol 14-alpha demethylase Enzyme INHIBITOR CHEMBL CHEMBL
Beta-lactamase Enzyme IC50 4.60 CHEMBL
Androgen receptor Transcription factor Ki 5.17 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 5.00 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 5.50 DRUG MATRIX
Progesterone receptor Transcription factor Ki 5.88 DRUG MATRIX
Alpha-1A adrenergic receptor GPCR IC50 4.67 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 4.79 CHEMBL
Acetylcholinesterase Enzyme IC50 4.65 CHEMBL
Cholinesterase Enzyme IC50 4.76 CHEMBL
Lanosterol 14-alpha demethylase Enzyme Kd 6.70 CHEMBL
Indoleamine 2,3-dioxygenase 2 Enzyme IC50 5.12 CHEMBL
Mycocyclosin synthase Enzyme Kd 7.14 CHEMBL
Indoleamine 2,3-dioxygenase 1 Enzyme IC50 4.95 CHEMBL

External reference:

IDSource
4019740 VUID
N0000147832 NUI
D00881 KEGG_DRUG
24169-02-6 SECONDARY_CAS_RN
4018560 VANDF
4019740 VANDF
C0013547 UMLSCUI
CHEBI:4754 CHEBI
CHEMBL808 ChEMBL_ID
CHEMBL1201049 ChEMBL_ID
DB01127 DRUGBANK_ID
D004464 MESH_DESCRIPTOR_UI
3198 PUBCHEM_CID
2446 IUPHAR_LIGAND_ID
3189 INN_ID
6Z1Y2V4A7M UNII
142434 RXNORM
400323 MMSL
45569 MMSL
4650 MMSL
002923 NDDF
002924 NDDF
18952006 SNOMEDCT_US
373471002 SNOMEDCT_US
73827006 SNOMEDCT_US
ECN PDB_CHEM_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 21695-892 CREAM 10 mg TOPICAL ANDA 17 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 21922-111 CREAM 10 mg TOPICAL ANDA 17 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 33261-956 CREAM 10 mg TOPICAL ANDA 17 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 45802-466 CREAM 10 mg TOPICAL ANDA 17 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 51672-1303 CREAM 10 mg TOPICAL ANDA 20 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 52565-022 CREAM 10 mg TOPICAL ANDA 18 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 54868-5042 CREAM 10 mg TOPICAL ANDA 17 sections
ECONAZOLE NITRATE Human Prescription Drug Label 1 59651-945 CREAM 10 mg TOPICAL ANDA 17 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 63629-8645 CREAM 10 mg TOPICAL ANDA 17 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 63629-8646 CREAM 10 mg TOPICAL ANDA 17 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 63629-8647 CREAM 10 mg TOPICAL ANDA 17 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 67296-0479 CREAM 10 mg TOPICAL ANDA 17 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 67296-1239 CREAM 10 mg TOPICAL ANDA 20 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 68788-8170 CREAM 10 mg TOPICAL ANDA 17 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 68788-8174 CREAM 10 mg TOPICAL ANDA 20 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 68788-8884 CREAM 10 mg TOPICAL ANDA 17 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 72162-1410 CREAM 10 mg TOPICAL ANDA 17 sections
PM EXTERNAL HUMAN OTC DRUG LABEL 4 72689-0038 SOLUTION 10 mg TOPICAL unapproved drug other 7 sections
ECONAZOLE NITRATE 1% / NIACINAMIDE 4% HUMAN PRESCRIPTION DRUG LABEL 2 72934-2073 CREAM 1 g TOPICAL unapproved drug other 4 sections
071023 ECONAZOLE NITRATE 1% / NIACINAMIDE 4% HUMAN PRESCRIPTION DRUG LABEL 2 72934-2218 CREAM 1 g TOPICAL unapproved drug other 4 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 73352-100 AEROSOL, FOAM 10 mg TOPICAL NDA 30 sections
Econazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 73352-100 AEROSOL, FOAM 10 mg TOPICAL NDA 30 sections
Ecoza HUMAN PRESCRIPTION DRUG LABEL 1 81811-100 AEROSOL, FOAM 10 mg TOPICAL NDA 30 sections