itraconazole indications/contra

Stem definitionDrug idCAS RN
systemic antifungal agents, miconazole derivatives 1513 84625-61-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • itraconazole
  • canditral
  • itrizole
  • oriconazole
  • traconal
  • triasporin
  • R-51211
A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.
  • Molecular weight: 705.64
  • Formula: C35H38Cl2N8O4
  • CLOGP: 5.99
  • LIPINSKI: 3
  • HAC: 12
  • HDO: 0
  • TPSA: 100.79
  • ALOGS: -4.86
  • ROTB: 11

Drug dosage:

DoseUnitRoute
0.20 g O
0.20 g P

Approvals:

DateAgencyCompanyOrphan
Sept. 11, 1992 FDA JANSSEN 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 1034.35 34.43 332 2507 46480 3336540
Drug ineffective 282.53 34.43 176 2663 115914 3267106
Bronchopulmonary aspergillosis 275.30 34.43 61 2778 1938 3381082
Hepatic function abnormal 254.17 34.43 82 2757 11145 3371875
Aspergillus infection 254.17 34.43 56 2783 1731 3381289
Pyrexia 206.68 34.43 127 2712 80988 3302032
Renal impairment 179.68 34.43 72 2767 18189 3364831
Oedema peripheral 174.24 34.43 85 2754 34276 3348744
Ileus paralytic 172.24 34.43 40 2799 1568 3381452
Hypokalaemia 169.70 34.43 64 2775 13741 3369279
Histoplasmosis 158.34 34.43 30 2809 424 3382596
Drug resistance 147.20 34.43 44 2795 4619 3378401
Drug eruption 143.10 34.43 44 2795 5081 3377939
Cardiac failure 133.50 34.43 60 2779 20045 3362975
Dyspnoea 132.01 34.43 106 2733 102828 3280192
Liver disorder 131.39 34.43 49 2790 10174 3372846
Rhabdomyolysis 130.72 34.43 55 2784 15674 3367346
Systemic mycosis 126.78 34.43 23 2816 252 3382768
Condition aggravated 124.48 34.43 71 2768 39162 3343858
Blood creatine phosphokinase increased 119.91 34.43 49 2790 12964 3370056
Electrocardiogram QT prolonged 118.06 34.43 46 2793 10749 3372271
Alanine aminotransferase increased 115.20 34.43 57 2782 23583 3359437
Aspartate aminotransferase increased 106.10 34.43 52 2787 21061 3361959
Neuropathy peripheral 104.69 34.43 48 2791 16759 3366261
Respiratory failure 104.50 34.43 53 2786 23088 3359932
Cushing's syndrome 104.32 34.43 25 2814 1121 3381899
Liver function test abnormal 103.43 34.43 44 2795 12857 3370163
Oedema 101.17 34.43 45 2794 14635 3368385
Erythema multiforme 99.61 34.43 30 2809 3223 3379797
Interstitial lung disease 96.70 34.43 43 2796 13973 3369047

Pharmacologic Action:

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SourceCodeDescription
ATC J02AC02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOTICS FOR SYSTEMIC USE
ANTIMYCOTICS FOR SYSTEMIC USE
Triazole derivatives
FDA EPC N0000175487 Azole Antifungal
FDA Chemical/Ingredient N0000008217 Azoles
FDA MoA N0000182141 Cytochrome P450 3A4 Inhibitors
FDA MoA N0000185503 P-Glycoprotein Inhibitors
MeSH PA D058888 14-alpha Demethylase Inhibitors
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000935 Antifungal Agents
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

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Invasive pulmonary aspergillosis indication 3214003
Histoplasmosis indication 12962009 DOID:1731
Candidiasis of the esophagus indication 20639004 DOID:13146
Fusarium infection indication 64250002
Aspergillosis indication 65553006 DOID:13564
Blastomycosis indication 69996000 DOID:12663
Disseminated candidiasis indication 70572005
Onychomycosis of fingernails indication 403058003
Onychomycosis of toenails indication 403059006
Candidemia indication 432261003
Fungal Infection due to Fusarium Solani indication
Oropharyngeal Candidiasis indication
Fungal Infection due to Scedosporium Apiospermum indication
Heart valve disorder contraindication 368009 DOID:4079
Hypocalcemia contraindication 5291005
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Hearing loss contraindication 15188001
Torsades de pointes contraindication 31722008
Hypokalemia contraindication 43339004
Ventricular arrhythmia contraindication 44103008
Achlorhydria contraindication 47481007
Chronic heart failure contraindication 48447003
Hypochlorhydria contraindication 55961006
Heart failure contraindication 84114007 DOID:6000
Cardiomyopathy contraindication 85898001 DOID:0050700
Kidney disease contraindication 90708001 DOID:2527
Prolonged QT interval contraindication 111975006
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Drug-induced hepatitis contraindication 235876009
Edema contraindication 267038008
Pregnancy, function contraindication 289908002
Peripheral nerve disease contraindication 302226006 DOID:574
Visual impairment contraindication 397540003
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Poor metabolizer due to cytochrome p450 CYP2C19 variant contraindication 424500005
Congenital long QT syndrome contraindication 442917000
Coccidioidomycosis off-label use 60826002 DOID:13450
Chromoblastomycosis off-label use 187079000 DOID:1562
Infection due to Penicillium marneffei off-label use 372936000
Onychomycosis due to dermatophyte off-label use 402134005

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.12 Basic
pKa2 5.0 Basic
pKa3 3.04 Basic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
200MG ONMEL SEBELA IRELAND LTD N022484 April 29, 2010 RX TABLET ORAL 8486456 Oct. 3, 2028 ONYCHOMYCOSIS OF THE TOENAIL CAUSED BY TRICOPHYTON RUBRUM OR TRICHOPHYTON MENTAGROPHYTES, ONCE DAILY USE FOR 12 CONSECUTIVE WEEKS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Cytochrome P450 3A4 Enzyme IC50 6.05 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.41 DRUG MATRIX
Vasopressin V2 receptor GPCR IC50 6.10 CHEMBL
Lanosterol 14-alpha demethylase Enzyme IC50 5.44 CHEMBL
C-C chemokine receptor type 4 GPCR IC50 6.70 CHEMBL
C-X-C chemokine receptor type 1 GPCR IC50 7 CHEMBL
Beta-2 adrenergic receptor GPCR Ki 6.30 CHEMBL
Lanosterol 14-alpha demethylase Enzyme INHIBITOR MIC 9.25 WOMBAT-PK CHEMBL
Cruzipain Enzyme IC50 5.52 CHEMBL
14-alpha sterol demethylase Enzyme Kd 7.51 CHEMBL
14-alpha sterol demethylase Cyp51A Enzyme Kd 6 CHEMBL

External reference:

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IDSource
4020560 VUID
N0000148264 NUI
C0064113 UMLSCUI
D00350 KEGG_DRUG
CHEMBL22587 ChEMBL_ID
304NUG5GF4 UNII
5387 INN_ID
4020560 VANDF
64593 MMSL
N0000006753 NDFRT
N0000148264 NDFRT
28031 RXNORM
387532006 SNOMEDCT_US
96038009 SNOMEDCT_US
4940 MMSL
d00102 MMSL
003915 NDDF
CHEMBL1711 ChEMBL_ID
DB01167 DRUGBANK_ID
55283 PUBCHEM_CID
D017964 MESH_DESCRIPTOR_UI
CHEBI:6076 CHEBI
1YN PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 0185-0550 CAPSULE 100 mg ORAL ANDA 14 sections
Onmel HUMAN PRESCRIPTION DRUG LABEL 1 0259-1420 TABLET 200 mg ORAL NDA 19 sections
Itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 0378-5100 CAPSULE 100 mg ORAL ANDA 14 sections
itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 10147-1700 CAPSULE 100 mg ORAL NDA 14 sections
Itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 16714-743 CAPSULE, COATED PELLETS 100 mg ORAL ANDA 13 sections
Itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 16729-271 CAPSULE 100 mg ORAL ANDA 15 sections
ITRACONAZOLE HUMAN PRESCRIPTION DRUG LABEL 1 46708-204 CAPSULE 100 mg ORAL ANDA 13 sections
Itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 49884-239 CAPSULE 100 mg ORAL ANDA 14 sections
SPORANOX HUMAN PRESCRIPTION DRUG LABEL 1 50458-290 CAPSULE 100 mg ORAL NDA 14 sections
SPORANOX HUMAN PRESCRIPTION DRUG LABEL 1 50458-295 SOLUTION 10 mg ORAL NDA 15 sections
itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 59746-282 CAPSULE 100 mg ORAL ANDA 14 sections
Itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 60687-299 CAPSULE 100 mg ORAL ANDA 13 sections
ITRACONAZOLE HUMAN PRESCRIPTION DRUG LABEL 1 62332-204 CAPSULE 100 mg ORAL ANDA 13 sections
SPORANOX HUMAN PRESCRIPTION DRUG LABEL 1 63629-1647 CAPSULE 100 mg ORAL NDA 14 sections
Itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 65162-087 SOLUTION 10 mg ORAL ANDA 15 sections
Itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 65162-630 CAPSULE 100 mg ORAL ANDA 13 sections
Itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 67877-454 CAPSULE, COATED PELLETS 100 mg ORAL ANDA 13 sections
itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 68151-2718 CAPSULE 100 mg ORAL NDA 15 sections
itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 68382-697 CAPSULE 100 mg ORAL ANDA 14 sections
itraconazole HUMAN PRESCRIPTION DRUG LABEL 1 70771-1208 CAPSULE 100 mg ORAL ANDA 14 sections