miconazole indications/contra

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

Drug dosage:

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

Approvals:

DateAgencyCompanyOrphan
Jan. 8, 1974 FDA INSIGHT PHARMS

FDA Adverse Event Reporting System

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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
Drug interaction 680.16 70.64 148 197 46664 3338850
International normalised ratio increased 527.38 70.64 100 245 14515 3370999
Haematuria 119.53 70.64 28 317 9924 3375590
Haemorrhage subcutaneous 103.14 70.64 17 328 963 3384551
Maternal drugs affecting foetus 91.88 70.64 19 326 3752 3381762

Pharmacologic Action:

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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 EPC N0000175487 Azole Antifungal
FDA Chemical/Ingredient N0000008217 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 D006730 Hormones, Hormone Substitutes, and Hormone Antagonists
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D065088 Steroid Synthesis Inhibitors
CHEBI has role CHEBI:35610 antineoplastic agent

Drug Use (View source of the data)

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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 DOID:12179
Diaper rash indication 91487003
Tinea cruris indication 399029005
Onychomycosis due to dermatophyte indication 402134005
Oropharyngeal Candidiasis indication
Disease of liver contraindication 235856003 DOID:409
Paronychia off-label use 71906005 DOID:13117

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 6.49 Basic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
50MG ORAVIG MIDATECH PHARMA US N022404 April 16, 2010 RX TABLET BUCCAL 6916485 Sept. 11, 2022 TREATMENT OF OROPHARYNGEAL CANDIDIASIS
50MG ORAVIG MIDATECH PHARMA US N022404 April 16, 2010 RX TABLET BUCCAL 7651698 Sept. 11, 2022 TREATMENT OF OROPHARYNGEAL CANDIDIASIS
0.25% VUSION MYLAN PHARMS INC 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:

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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:

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IDSource
2449 IUPHAR_LIGAND_ID
4018555 VUID
N0000146875 NUI
C0025942 UMLSCUI
D00416 KEGG_DRUG
CHEMBL91 ChEMBL_ID
7NNO0D7S5M UNII
2728 INN_ID
DB01110 DRUGBANK_ID
4018555 VANDF
7143 MMSL
6932 RXNORM
372738006 SNOMEDCT_US
42720001 SNOMEDCT_US
5112 MMSL
d00155 MMSL
N0000006565 NDFRT
N0000146875 NDFRT
002918 NDDF
CHEMBL1559 ChEMBL_ID
4189 PUBCHEM_CID
D008825 MESH_DESCRIPTOR_UI
22832-87-7 SECONDARY_CAS_RN
CHEBI:6923 CHEBI
X89 PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Desenex HUMAN OTC DRUG LABEL 1 0067-0949 POWDER 2 g TOPICAL OTC monograph final 14 sections
Vagistat-3 HUMAN OTC DRUG LABEL 2 0067-2091 KIT 200 mg None ANDA 10 sections
Vagistat-3 HUMAN OTC DRUG LABEL 2 0067-2091 KIT 2 g None ANDA 10 sections
Good Sense Miconazole 3 HUMAN OTC DRUG LABEL 2 0113-0081 KIT 200 mg None ANDA 10 sections
Good Sense Miconazole 3 HUMAN OTC DRUG LABEL 2 0113-0081 KIT 2 g None ANDA 10 sections
Miconazole nitrate HUMAN OTC DRUG LABEL 1 0113-0136 AEROSOL, SPRAY 3 g TOPICAL OTC monograph final 9 sections
Good Sense Miconazole 7 HUMAN OTC DRUG LABEL 1 0113-0214 CREAM 2 g VAGINAL ANDA 10 sections
good sense miconazole 7 HUMAN OTC DRUG LABEL 1 0113-0825 CREAM 2 g VAGINAL ANDA 10 sections
good sense miconazole 1 HUMAN OTC DRUG LABEL 2 0113-0916 KIT 1200 mg None ANDA 10 sections
good sense miconazole 1 HUMAN OTC DRUG LABEL 2 0113-0916 KIT 2 g None ANDA 10 sections
Basic Care miconazole 1 HUMAN OTC DRUG LABEL 2 0113-7199 KIT 1200 mg None ANDA 10 sections
Basic Care miconazole 1 HUMAN OTC DRUG LABEL 2 0113-7199 KIT 2 g None ANDA 10 sections
Zeasorb HUMAN OTC DRUG LABEL 1 0145-1501 POWDER 20.60 mg TOPICAL OTC monograph final 9 sections
Zeasorb HUMAN OTC DRUG LABEL 1 0145-1506 POWDER 20.60 mg TOPICAL OTC monograph final 9 sections
Selan Antifungal HUMAN OTC DRUG LABEL 1 0159-2500 CREAM 2 g TOPICAL OTC monograph final 12 sections
Kaiser Permanente HUMAN OTC DRUG LABEL 1 0179-8017 CREAM 20 mg TOPICAL OTC MONOGRAPH FINAL 10 sections
PreviSense Antifungal Moisture Barrier with Protease Technology HUMAN OTC DRUG LABEL 1 0234-8578 CREAM 2 g TOPICAL OTC monograph final 8 sections
Miconazole 3 HUMAN OTC DRUG LABEL 2 0363-0081 KIT 2 g None ANDA 10 sections
Miconazole 3 HUMAN OTC DRUG LABEL 2 0363-0081 KIT 200 mg None ANDA 10 sections
Miconazole 1 HUMAN OTC DRUG LABEL 2 0363-0199 KIT 2 g None ANDA 10 sections
Miconazole 1 HUMAN OTC DRUG LABEL 2 0363-0199 KIT 1200 mg None ANDA 10 sections
Athletes Foot HUMAN OTC DRUG LABEL 1 0363-0557 SPRAY 2 g TOPICAL OTC monograph final 9 sections
Miconazole 3 HUMAN OTC DRUG LABEL 2 0363-0637 KIT 2 g None ANDA 10 sections
Miconazole 3 HUMAN OTC DRUG LABEL 2 0363-0637 KIT 4 g None ANDA 10 sections
Miconazole 7 HUMAN OTC DRUG LABEL 1 0363-0730 CREAM 20 mg VAGINAL ANDA 10 sections
Miconazole 1 HUMAN OTC DRUG LABEL 2 0363-0737 KIT 2 g None ANDA 10 sections
Miconazole 1 HUMAN OTC DRUG LABEL 2 0363-0737 KIT 1200 mg None ANDA 10 sections
miconazole 1 HUMAN OTC DRUG LABEL 2 0363-0916 KIT 2 g None ANDA 10 sections
miconazole 1 HUMAN OTC DRUG LABEL 2 0363-0916 KIT 1200 mg None ANDA 10 sections
Jock Itch HUMAN OTC DRUG LABEL 1 0363-1497 SPRAY 2 g TOPICAL OTC monograph final 9 sections