miconazole ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
systemic antifungal agents, miconazole derivatives 1800 22916-47-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • miconazole
  • miconazole nitrate
An imidazole antifungal agent that is used topically and by intravenous infusion.
  • Molecular weight: 416.12
  • Formula: C18H14Cl4N2O
  • CLOGP: 5.81
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 0
  • TPSA: 27.05
  • ALOGS: -5.74
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 g O
1 g O
0.10 g V
1 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.89 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 144.18 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 25 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 7.14 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 9.48 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.08 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 19.75 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 8, 1974 FDA INSIGHT PHARMS
Dec. 30, 1985 PMDA

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
International normalised ratio increased 228.03 16.56 103 5010 43049 50556962
Drug interaction 189.29 16.56 158 4955 199463 50400548
Cholestasis of pregnancy 58.29 16.56 15 5098 1116 50598895
Haemorrhage subcutaneous 45.40 16.56 15 5098 2686 50597325
Vulvovaginal burning sensation 44.09 16.56 13 5100 1602 50598409
Haematuria 41.33 16.56 28 5085 25585 50574426
Sepsis neonatal 39.05 16.56 9 5104 421 50599590
Pericardial effusion 38.98 16.56 27 5086 25562 50574449
Encephalitis fungal 38.98 16.56 6 5107 27 50599984
Nail dystrophy 28.74 16.56 8 5105 803 50599208
Lip swelling 28.39 16.56 22 5091 24714 50575297
Cancer pain 26.71 16.56 10 5103 2577 50597434
Haematoma 26.35 16.56 23 5090 30487 50569524
Vaginal erosion 24.49 16.56 4 5109 28 50599983
Axillary pain 23.46 16.56 8 5105 1576 50598435
Vulvovaginal pruritus 23.43 16.56 9 5104 2487 50597524
Vulvovaginal candidiasis 22.77 16.56 9 5104 2683 50597328
Drug ineffective 22.61 16.56 30 5083 819303 49780708
Drug withdrawal syndrome neonatal 22.28 16.56 8 5105 1833 50598178
Premature labour 22.05 16.56 14 5099 11462 50588549
Drug hypersensitivity 20.75 16.56 64 5049 250946 50349065
Jarisch-Herxheimer reaction 20.65 16.56 5 5108 290 50599721
Hypokalaemia 20.56 16.56 34 5079 87958 50512053
Hydronephrosis 20.46 16.56 12 5101 8529 50591482
Eosinophilia 20.13 16.56 16 5097 18636 50581375
Rash erythematous 20.05 16.56 21 5092 34831 50565180
Neuropathy peripheral 19.48 16.56 35 5078 96722 50503289
Vulvovaginal swelling 18.66 16.56 5 5108 435 50599576
Pneumomediastinum 17.77 16.56 6 5107 1147 50598864
Fungal sepsis 17.77 16.56 6 5107 1148 50598863
Vulvovaginal pain 17.36 16.56 7 5106 2198 50597813
Vulvovaginal inflammation 17.11 16.56 5 5108 597 50599414

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
International normalised ratio increased 162.49 19.02 82 2881 44290 29527274
Drug interaction 146.37 19.02 135 2828 197250 29374314
Haematuria 30.06 19.02 29 2934 44110 29527454
Coagulation time prolonged 29.90 19.02 9 2954 1201 29570363
Oedema genital 29.73 19.02 7 2956 363 29571201
Ocular myasthenia 27.51 19.02 6 2957 220 29571344
Pharyngeal haematoma 21.94 19.02 4 2959 57 29571507
Haemorrhage subcutaneous 21.23 19.02 8 2955 2117 29569447

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
International normalised ratio increased 298.56 16.46 152 6668 79015 64412897
Drug interaction 247.47 16.46 243 6577 361840 64130072
Cholestasis of pregnancy 50.68 16.46 13 6807 912 64491000
Haematuria 49.31 16.46 45 6775 60426 64431486
Sepsis neonatal 36.21 16.46 6 6814 44 64491868
Pericardial effusion 29.64 16.46 28 6792 39226 64452686
Nail dystrophy 28.36 16.46 8 6812 805 64491107
Oedema genital 27.78 16.46 7 6813 457 64491455
Drug withdrawal syndrome neonatal 26.53 16.46 6 6814 246 64491666
Lip swelling 26.49 16.46 24 6796 31883 64460029
Cancer pain 24.62 16.46 11 6809 4246 64487666
Vulvovaginal candidiasis 24.42 16.46 9 6811 2121 64489791
Coagulation time prolonged 24.36 16.46 9 6811 2137 64489775
Ocular myasthenia 24.14 16.46 6 6814 370 64491542
Haematoma 24.06 16.46 27 6793 46223 64445689
Premature labour 23.97 16.46 13 6807 7607 64484305
Hypokalaemia 22.98 16.46 44 6776 121859 64370053
Axillary pain 22.40 16.46 8 6812 1724 64490188
Haemorrhage subcutaneous 21.23 16.46 10 6810 4351 64487561
Labelled drug-drug interaction medication error 21.13 16.46 18 6802 22044 64469868
Premature baby 20.68 16.46 9 6811 3263 64488649
Seizure 19.80 16.46 50 6770 166842 64325070
Pharyngeal haematoma 19.34 16.46 4 6816 107 64491805
Contusion 18.91 16.46 39 6781 113926 64377986
Pneumomediastinum 18.40 16.46 8 6812 2892 64489020
Urinary tract infection 18.35 16.46 60 6760 231536 64260376
Eosinophilia 17.73 16.46 21 6799 38055 64453857
Rash erythematous 16.62 16.46 23 6797 48610 64443302

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC A01AB09 ALIMENTARY TRACT AND METABOLISM
STOMATOLOGICAL PREPARATIONS
STOMATOLOGICAL PREPARATIONS
Antiinfectives and antiseptics for local oral treatment
ATC A07AC01 ALIMENTARY TRACT AND METABOLISM
ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
INTESTINAL ANTIINFECTIVES
Imidazole derivatives
ATC D01AC02 DERMATOLOGICALS
ANTIFUNGALS FOR DERMATOLOGICAL USE
ANTIFUNGALS FOR TOPICAL USE
Imidazole and triazole derivatives
ATC D01AC52 DERMATOLOGICALS
ANTIFUNGALS FOR DERMATOLOGICAL USE
ANTIFUNGALS FOR TOPICAL USE
Imidazole and triazole derivatives
ATC G01AF04 GENITO URINARY SYSTEM AND SEX HORMONES
GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
Imidazole derivatives
ATC J02AB01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOTICS FOR SYSTEMIC USE
ANTIMYCOTICS FOR SYSTEMIC USE
Imidazole derivatives
ATC S02AA13 SENSORY ORGANS
OTOLOGICALS
ANTIINFECTIVES
Antiinfectives
FDA CS M0002083 Azoles
FDA EPC N0000175487 Azole Antifungal
MeSH PA D058888 14-alpha Demethylase Inhibitors
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000935 Antifungal Agents
MeSH PA D065688 Cytochrome P-450 CYP2C9 Inhibitors
MeSH PA D065692 Cytochrome P-450 CYP3A Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D006727 Hormone Antagonists
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D065088 Steroid Synthesis Inhibitors
CHEBI has role CHEBI:35610 antineoplastic agents
CHEBI has role CHEBI:75282 ergosterol biosynthesis inhibitors
CHEBI has role CHEBI:82891 glucocorticoid receptor antagonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Tinea pedis indication 6020002 DOID:12403
Candidiasis of skin indication 49883006
Pityriasis versicolor indication 56454009 DOID:9060
Candidal vulvovaginitis indication 72605008 DOID:2272
Candidiasis of mouth indication 79740000 DOID:14262
Tinea corporis indication 84849002
Diaper rash indication 91487003
Tinea cruris indication 399029005
Onychomycosis due to dermatophyte indication 402134005
Deep mycosis indication 716203000
Oropharyngeal Candidiasis indication
Paronychia off-label use 71906005 DOID:13117
Disease of liver contraindication 235856003 DOID:409




๐Ÿถ Veterinary Drug Use

SpeciesUseRelation
Cats Infections caused by Microsporum canis Indication
Cats Infections caused by Microsporum gypseum Indication
Cats Infections caused by Trichophyton mentagrophytes Indication
Dogs Infections caused by Microsporum canis Indication
Dogs Infections caused by Microsporum gypseum Indication
Dogs Infections caused by Trichophyton mentagrophytes Indication

๐Ÿถ Veterinary products

ProductApplicantIngredients
Conofite Cream 2% Intervet Inc. 1
Conofite Lotion 1% Intervet Inc. 1
Surolan Elanco US Inc. 3
Easotic Virbac AH Inc. 3
Miconosol Med-Pharmex Inc. 1
Priconazole Lotion 1% and Spray 1% First Priority Inc. 1

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
50MG ORAVIG GALT PHARMS N022404 April 16, 2010 RX TABLET BUCCAL 6916485 Sept. 11, 2022 TREATMENT OF OROPHARYNGEAL CANDIDIASIS
50MG ORAVIG GALT PHARMS N022404 April 16, 2010 RX TABLET BUCCAL 7651698 Sept. 11, 2022 TREATMENT OF OROPHARYNGEAL CANDIDIASIS
0.25%;81.35%;15% VUSION MYLAN N021026 Feb. 16, 2006 RX OINTMENT TOPICAL 8147852 March 30, 2028 USE FOR TREATMENT OF DIAPER DERMATITIS COMPLICATED BY CANDIDIASIS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Beta-1 adrenergic receptor GPCR Ki 5.14 DRUG MATRIX
Prostaglandin G/H synthase 2 Enzyme IC50 4.59 DRUG MATRIX
Cannabinoid receptor 1 GPCR Ki 4.78 DRUG MATRIX
Mu-type opioid receptor GPCR Ki 5.61 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 5.51 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 5.38 DRUG MATRIX
Adenosine receptor A2a GPCR Ki 5.10 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 5.83 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel WOMBAT-PK
Cytochrome P450 3A4 Enzyme IC50 7 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 6.38 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.54 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 5.18 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 5.95 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 5.45 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 5.56 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 5.30 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 5.79 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 5.96 DRUG MATRIX
Histamine H2 receptor GPCR Ki 5.18 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 6.02 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 5.81 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 6.18 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.35 DRUG MATRIX
Beta-3 adrenergic receptor GPCR Ki 5.39 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.87 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 6 DRUG MATRIX
Adenosine receptor A1 GPCR Ki 5.14 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.80 DRUG MATRIX
D(4) dopamine receptor GPCR Ki 5.27 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 5.83 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 5.58 DRUG MATRIX
Delta-type opioid receptor GPCR Ki 5.92 DRUG MATRIX
Acetylcholinesterase Enzyme IC50 4.73 DRUG MATRIX
Cytochrome P450 2C9 Enzyme IC50 6.70 DRUG MATRIX
Aromatase Enzyme IC50 6.22 CHEMBL
Epidermal growth factor receptor Kinase IC50 4.53 DRUG MATRIX
Substance-P receptor GPCR Ki 5.43 DRUG MATRIX
Steroid 17-alpha-hydroxylase/17,20 lyase Enzyme Ki 6.61 CHEMBL
Cytochrome P450 2C19 Enzyme IC50 7.80 DRUG MATRIX
Alkaline phosphatase, tissue-nonspecific isozyme Enzyme EC50 4.15 CHEMBL
Tyrosine-protein kinase Fyn Kinase IC50 5.38 DRUG MATRIX
Receptor tyrosine-protein kinase erbB-2 Kinase IC50 4.56 DRUG MATRIX
Thromboxane-A synthase Enzyme IC50 6.58 DRUG MATRIX
Lanosterol 14-alpha demethylase Enzyme IC50 6.70 CHEMBL
Indoleamine 2,3-dioxygenase 1 Enzyme IC50 5.42 CHEMBL
Type-2 angiotensin II receptor GPCR Ki 5.11 DRUG MATRIX
Substance-K receptor GPCR Ki 5.79 DRUG MATRIX
Melanocortin receptor 4 GPCR Ki 4.92 DRUG MATRIX
Melanocortin receptor 5 GPCR Ki 4.67 DRUG MATRIX
Melanocortin receptor 3 GPCR Ki 4.79 DRUG MATRIX
Malate dehydrogenase cytoplasmic Enzyme IC50 4.60 CHEMBL
Calcium release-activated calcium channel protein 1 Ion channel IC50 4.57 CHEMBL
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase Enzyme IC50 5.82 CHEMBL
Lanosterol 14-alpha demethylase Enzyme INHIBITOR CHEMBL CHEMBL
Beta-lactamase Enzyme IC50 4.40 CHEMBL
Androgen receptor Transcription factor Ki 5.33 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 5.03 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 5.69 DRUG MATRIX
Progesterone receptor Transcription factor Ki 5.71 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR IC50 4.94 CHEMBL
Acetylcholinesterase Enzyme IC50 4.67 CHEMBL
Aromatase Enzyme EC50 6.40 CHEMBL
Cholinesterase Enzyme IC50 5.17 CHEMBL
Lanosterol 14-alpha demethylase Enzyme Kd 6.70 CHEMBL
Indoleamine 2,3-dioxygenase 2 Enzyme IC50 5.17 CHEMBL
Mycocyclosin synthase Enzyme Kd 7.14 CHEMBL
Indoleamine 2,3-dioxygenase 1 Enzyme IC50 4.75 CHEMBL
Fatty acid hydroperoxide lyase, chloroplastic Enzyme IC50 4.19 CHEMBL
Sodium/potassium-transporting ATPase subunit alpha-2 Ion channel IC50 4.72 DRUG MATRIX

External reference:

IDSource
4018555 VUID
N0000146875 NUI
D00416 KEGG_DRUG
22832-87-7 SECONDARY_CAS_RN
4018554 VANDF
4018555 VANDF
C0025942 UMLSCUI
CHEBI:6923 CHEBI
CHEMBL91 ChEMBL_ID
CHEMBL1559 ChEMBL_ID
D008825 MESH_DESCRIPTOR_UI
DB01110 DRUGBANK_ID
4189 PUBCHEM_CID
2449 IUPHAR_LIGAND_ID
2728 INN_ID
7NNO0D7S5M UNII
42790 RXNORM
1135 MMSL
36502 MMSL
5112 MMSL
5113 MMSL
7143 MMSL
d00155 MMSL
002918 NDDF
002919 NDDF
372738006 SNOMEDCT_US
42720001 SNOMEDCT_US
60727003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Good Sense Miconazole 7 HUMAN OTC DRUG LABEL 1 0113-0214 CREAM 2 g VAGINAL ANDA 17 sections
good sense miconazole 7 HUMAN OTC DRUG LABEL 1 0113-0825 CREAM 2 g VAGINAL ANDA 17 sections
basic care miconazole 3 HUMAN OTC DRUG LABEL 1 0113-7070 CREAM 40 mg VAGINAL ANDA 17 sections
basic care miconazole 7 HUMAN OTC DRUG LABEL 1 0113-7825 CREAM 2 g VAGINAL ANDA 17 sections
Selan Antifungal HUMAN OTC DRUG LABEL 1 0159-2500 CREAM 2 g TOPICAL OTC monograph final 12 sections
Selan Antifungal HUMAN OTC DRUG LABEL 1 0159-2500 CREAM 2 g TOPICAL OTC monograph final 12 sections
Desenex HUMAN OTC DRUG LABEL 1 0316-0225 POWDER 20 mg TOPICAL OTC monograph final 13 sections
Zeasorb HUMAN OTC DRUG LABEL 1 0316-0231 POWDER 20 mg TOPICAL OTC monograph final 12 sections
Zeasorb HUMAN OTC DRUG LABEL 1 0316-0232 POWDER 20 mg TOPICAL OTC monograph final 12 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 0363-0557 SPRAY 2 g TOPICAL OTC monograph final 13 sections
Miconazole 7 HUMAN OTC DRUG LABEL 1 0363-0730 CREAM 20 mg VAGINAL ANDA 17 sections
Jock Itch HUMAN OTC DRUG LABEL 1 0363-1497 SPRAY 2 g TOPICAL OTC monograph final 13 sections
miconazole 3 HUMAN OTC DRUG LABEL 1 0363-2070 CREAM 40 mg VAGINAL ANDA 17 sections
Miconazole Nitrate HUMAN OTC DRUG LABEL 1 0363-3115 POWDER 1.42 g TOPICAL OTC monograph final 13 sections
Miconazole Nitrate HUMAN OTC DRUG LABEL 1 0363-4208 SPRAY 3 g TOPICAL OTC monograph final 13 sections
Miconazole Nitrate 2% HUMAN OTC DRUG LABEL 1 0363-5353 AEROSOL, SPRAY 1.30 g TOPICAL OTC monograph final 14 sections
Miconazole Nitrate HUMAN OTC DRUG LABEL 1 0363-7418 AEROSOL, SPRAY 2.60 g TOPICAL OTC monograph final 13 sections
VUSION HUMAN PRESCRIPTION DRUG LABEL 3 0378-8222 OINTMENT 2.50 mg TOPICAL NDA authorized generic 26 sections
VUSION HUMAN PRESCRIPTION DRUG LABEL 3 0378-9730 OINTMENT 2.50 mg TOPICAL NDA 26 sections
Miconazole 7 HUMAN OTC DRUG LABEL 1 0472-0730 CREAM 20 mg VAGINAL ANDA 17 sections
Antifungal HUMAN OTC DRUG LABEL 1 0472-0735 CREAM 20 mg TOPICAL OTC monograph final 13 sections
Miconazole 7 HUMAN OTC DRUG LABEL 1 0472-1736 SUPPOSITORY 100 mg VAGINAL ANDA 17 sections
Miconazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 0472-1738 SUPPOSITORY 200 mg VAGINAL ANDA 16 sections
Miconazole Nitrate HUMAN OTC DRUG LABEL 1 0536-1134 CREAM 20 mg TOPICAL OTC MONOGRAPH FINAL 14 sections
Miconazole Nitrate HUMAN OTC DRUG LABEL 1 0713-0197 SUPPOSITORY 100 ug VAGINAL ANDA 11 sections
Miconazole Nitrate HUMAN OTC DRUG LABEL 1 0713-0252 CREAM 20 mg VAGINAL ANDA 11 sections
fungoid tincture HUMAN OTC DRUG LABEL 1 0884-0293 TINCTURE 20 mg TOPICAL OTC monograph final 12 sections
Miconazole 7 HUMAN OTC DRUG LABEL 1 0904-7734 CREAM 20 mg VAGINAL ANDA 16 sections
Miconazole Nitrate Antifungal Powder HUMAN OTC DRUG LABEL 1 10135-720 POWDER 2 g TOPICAL OTC monograph final 10 sections
TRIPLEAF HUMAN OTC DRUG LABEL 1 11086-040 PASTE 2 g TOPICAL OTC monograph final 11 sections