miconazole 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 µM/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

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 225.47 16.36 106 4790 46777 46634389
Drug interaction 177.81 16.36 156 4740 202938 46478228
Cholestasis of pregnancy 57.83 16.36 15 4881 1109 46680057
Haemorrhage subcutaneous 43.77 16.36 15 4881 2891 46678275
Sepsis neonatal 39.17 16.36 9 4887 400 46680766
Encephalitis fungal 38.76 16.36 6 4890 27 46681139
Pericardial effusion 38.12 16.36 27 4869 25516 46655650
Vulvovaginal burning sensation 35.29 16.36 11 4885 1575 46679591
Haematuria 34.66 16.36 26 4870 26832 46654334
Lip swelling 31.47 16.36 24 4872 25371 46655795
Full blood count abnormal 31.39 16.36 10 4886 1537 46679629
Premature labour 21.77 16.36 14 4882 11285 46669881
Drug withdrawal syndrome neonatal 21.63 16.36 8 4888 1920 46679246
Haematoma 20.97 16.36 21 4875 31851 46649315
Fungal infection 20.44 16.36 20 4876 29500 46651666
Jarisch-Herxheimer reaction 20.18 16.36 5 4891 307 46680859
Rash erythematous 19.66 16.36 21 4875 34329 46646837
Drug hypersensitivity 19.52 16.36 63 4833 243762 46437404
Drug monitoring procedure not performed 18.94 16.36 5 4891 396 46680770
Nail dystrophy 18.20 16.36 5 4891 460 46680706
Fungal sepsis 17.58 16.36 6 4890 1141 46680025
Vulvovaginal inflammation 17.18 16.36 5 4891 567 46680599
Eosinophilia 17.14 16.36 15 4881 19202 46661964
Vaginal erosion 16.72 16.36 3 4893 37 46681129
Vulvovaginal pruritus 16.40 16.36 7 4889 2440 46678726

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 160.94 17.53 84 2978 47655 29901761
Drug interaction 140.77 17.53 134 2928 199434 29749982
Coagulation time prolonged 29.55 17.53 9 3053 1225 29948191
Haematuria 29.18 17.53 29 3033 44805 29904611
Ocular myasthenia 26.88 17.53 6 3056 240 29949176
Haemorrhage subcutaneous 20.68 17.53 8 3054 2229 29947187
Mouth haemorrhage 20.23 17.53 10 3052 5007 29944409
Vitamin E deficiency 19.19 17.53 3 3059 15 29949401
Arthritis allergic 18.33 17.53 3 3059 21 29949395
Genital rash 17.79 17.53 5 3057 514 29948902
Tongue ulceration 17.76 17.53 6 3056 1136 29948280

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 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
ATC D01AC52 DERMATOLOGICALS
ANTIFUNGALS FOR DERMATOLOGICAL USE
ANTIFUNGALS FOR TOPICAL USE
Imidazole and triazole derivatives
FDA CS M0002083 Azoles
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
FDA EPC N0000175487 Azole Antifungal
CHEBI has role CHEBI:35610 cytostatic
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
Tinea corporis indication 84849002
Diaper rash indication 91487003
Tinea cruris indication 399029005
Onychomycosis due to dermatophyte indication 402134005
Oropharyngeal Candidiasis indication
Paronychia off-label use 71906005 DOID:13117
Disease of liver contraindication 235856003 DOID:409

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
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
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 5.78 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 5.82 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
Epidermal growth factor receptor Kinase IC50 4.53 DRUG MATRIX
Substance-P receptor GPCR Ki 5.43 DRUG MATRIX
Cytochrome P450 2C19 Enzyme IC50 7.80 DRUG MATRIX
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
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
Potassium voltage-gated channel subfamily H member 2 Ion channel WOMBAT-PK
Aromatase Enzyme IC50 6.22 CHEMBL
Malate dehydrogenase cytoplasmic Enzyme IC50 4.60 CHEMBL
Lanosterol 14-alpha demethylase Enzyme IC50 6.70 CHEMBL
Steroid 17-alpha-hydroxylase/17,20 lyase Enzyme Ki 6.61 CHEMBL
Alkaline phosphatase, tissue-nonspecific isozyme Enzyme EC50 4.15 CHEMBL
Indoleamine 2,3-dioxygenase 1 Enzyme IC50 5.42 CHEMBL
Beta-1 adrenergic receptor GPCR Ki 5.14 DRUG MATRIX
Lanosterol 14-alpha demethylase Enzyme INHIBITOR CHEMBL CHEMBL
Androgen receptor Transcription factor Ki 5.33 DRUG MATRIX
Sodium/potassium-transporting ATPase subunit alpha-2 Ion channel IC50 4.71 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
Indoleamine 2,3-dioxygenase 2 Enzyme IC50 5.17 CHEMBL
Aromatase Enzyme EC50 6.40 CHEMBL
Beta-lactamase Enzyme IC50 4.40 CHEMBL
Lanosterol 14-alpha demethylase Enzyme Kd 6.70 CHEMBL
Indoleamine 2,3-dioxygenase 1 Enzyme IC50 4.75 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 4.94 CHEMBL

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
2449 IUPHAR_LIGAND_ID
2728 INN_ID
7NNO0D7S5M UNII
4189 PUBCHEM_CID
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 VAGINULLL ANDA 17 sections
good sense miconazole 7 HUMAN OTC DRUG LABEL 1 0113-0825 CREAM 2 g VAGINULLL ANDA 17 sections
basic care miconazole 3 HUMAN OTC DRUG LABEL 1 0113-7070 CREAM 40 mg VAGINULLL ANDA 17 sections
basic care miconazole 7 HUMAN OTC DRUG LABEL 1 0113-7825 CREAM 2 g VAGINULLL ANDA 17 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 VAGINULLL 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 VAGINULLL 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
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 VAGINULLL ANDA 17 sections
Antifungal HUMAN OTC DRUG LABEL 1 0472-0735 CREAM 20 mg TOPICAL OTC MONOGRAPH FINULLL 13 sections
Miconazole 7 HUMAN OTC DRUG LABEL 1 0472-1736 SUPPOSITORY 100 mg VAGINULLL ANDA 17 sections
Miconazole Nitrate HUMAN PRESCRIPTION DRUG LABEL 1 0472-1738 SUPPOSITORY 200 mg VAGINULLL ANDA 16 sections
Miconazole Nitrate HUMAN OTC DRUG LABEL 1 0536-1134 CREAM 20 mg TOPICAL OTC MONOGRAPH FINULLL 14 sections
Miconazole Nitrate HUMAN OTC DRUG LABEL 1 0713-0197 SUPPOSITORY 100 ug VAGINULLL ANDA 11 sections
Miconazole Nitrate HUMAN OTC DRUG LABEL 1 0713-0252 CREAM 20 mg VAGINULLL 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 VAGINULLL ANDA 16 sections
TRIPLEAF HUMAN OTC DRUG LABEL 1 11086-040 PASTE 2 g TOPICAL OTC monograph final 11 sections
Aloe Vesta Clear Antifungal 56g HUMAN OTC DRUG LABEL 1 11099-0003 OINTMENT 1.12 g TOPICAL OTC monograph final 10 sections
Aloe Vesta Clear Antifungal 141g HUMAN OTC DRUG LABEL 1 11099-0006 OINTMENT 2.82 g TOPICAL OTC monograph final 10 sections
vagisil brand vagistat HUMAN OTC DRUG LABEL 1 11509-0825 CREAM 2 g VAGINULLL ANDA 17 sections
LotriminAntifungal HUMAN OTC DRUG LABEL 1 11523-0544 AEROSOL, POWDER 20 mg TOPICAL OTC monograph final 14 sections