Drug Details

General Information of the Drug (ID: DR8760)
Name
Itraconazole
Synonyms
itraconazole; Oriconazole; 84625-61-6; Sporanox; Itrizole (TN); Sporanox (TN); ITCZ; Itraconazole (Sporanox); Itraconazol [Spanish]; Itraconazolum [Latin]; CHEMBL22587; C35H38Cl2N8O4; cis-Itraconazole; CHEBI:6076; 2-butan-2-yl-4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one; ITZ; DSSTox_CID_3180; DSSTox_RID_76908; DSSTox_GSID_23180; 1-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one; 2-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one; 4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-sec-butyl-1,2,4-triazol-3-one; CAS-84625-61-6; R-51211; Intraconazole; Sporanox(TM); NCGC00018268-03; 4-(4-{4-[4-({[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl}oxy)phenyl]piperazin-1-yl}phenyl)-2-(1-methylpropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one; R51211; Itraconazole & Nyotran; Itraconazole (JP17/USP); SCHEMBL23934; 84604-65-9; MLS006011958; AMY922; DTXSID3023180; GTPL11426; Pharmakon1600-01505756; Tox21_110854; 2485AH; AC-542; BDBM50127138; CI0042; MFCD00941396; NSC759239; s2476; AKOS015842738; AKOS015961385; Tox21_110854_1; CCG-270391; DB01167; KS-1268; MCULE-2446846552; NE57775; NSC-759239; NCGC00274068-01; NCGC00274068-02; NCGC00274068-07; 4-(4-(4-(4-(((2R,4S)-2-((1H-1,2,4-triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-(sec-butyl)-2,4-dihydro-3H-1,2,4-triazol-3-one; 873066-43-4; HY-17514; SMR001827898; Itraconazole & Nyotran(Liposomal Nystatin); SBI-0206914.P001; AB0012897; SW219756-1; Itraconazole 2.0 mg/ml in Dimethyl Sulfoxide; D00350; 24236-EP2281816A1; 24236-EP2314590A1; AB01274818-01; AB01274818_02; AB01274818_03; Q411229; BRD-A23067620-001-01-7; 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-pipera-zinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl); 4-[4-[4-[4-[[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazole-1-ylmethyl)-1,3-dioxolane-4-yl]methoxy]phenyl]piperazino]phenyl]-2-(1-methylpropyl)-4H-1,2,4-triazole-3(2H)-one
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Molecular Type
Small molecule
Disease Fungal infection [ICD-11: 1F29-1F2F] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Bioavailability
The bioavailability of drug is 55%
Clearance
The drug present in the plasma can be removed from the body at the rate of 5.1 mL/min/kg
Elimination
0.03% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 21 hours
Metabolism
The drug is metabolized via the liver
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 14.17132 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.002%
Vd
The volume of distribution (Vd) of drug is 796 +/- 185 L
Water Solubility
The ability of drug to dissolve in water is measured as 0.000001 mg/mL
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Formula
C35H38Cl2N8O4
PubChem CID
55283
Canonical SMILES
CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5COC(O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl
InChI
1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1
InChIKey
VHVPQPYKVGDNFY-ZPGVKDDISA-N
CAS Number
CAS 84625-61-6
ChEBI ID
CHEBI:6076
TTD Drug ID
D0V4IB
DrugBank ID
DB01167
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Arsenic trioxide      Realgar and orpiment     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
Down-regulation Expression Gli1  Molecule Info 
Pathway MAP
                    In-vitro Model NCI-H929 CVCL_1600 Plasma cell myeloma Homo sapiens
                    Experimental
                    Result(s)		 ATO combined with ITRA can more strongly suppress the growth of multiple myeloma NCI-H929 cells, as compared with a single administration. The synergistic effect of ATO and ITRA significantly down-regulates expression of Gli1 in HH signaling pathway, moreover the inhibition of target gene overexpression may be one of two drug mechanisms.
          Menthol      Mentha x piperita     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Candida glabrata ATCC 90030 Microorganism model Candida glabrata
Candida krusei ATCC 6258 Microorganism model Candida krusei
                    Experimental
                    Result(s)		 Synergistic anticandidal activity of menthol in combination with itraconazole and nystatin against clinical Candida glabrata and Candida krusei isolates.
Target and Pathway
Target(s) Candida Cytochrome P450 51 (Candi ERG11)  Molecule Info  [4]
References
Reference 1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 076104.
Reference 2 [Synergistic Inhibitory Effect of Arsenic Trioxide Combined with Itraconazole on Hedgehog Pathway of Multiple Myeloma NCI-H929 Cells]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2016 Oct;24(5):1459-1465.
Reference 3 Synergistic anticandidal activity of menthol in combination with itraconazole and nystatin against clinical Candida glabrata and Candida krusei isolates. Microb Pathog. 2017 Jun;107:390-396.
Reference 4 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
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