Itraconazole

A broad-spectrum triazole antifungal drug used to treat systemic and superficial fungal infections, including aspergillosis, histoplasmosis, blastomycosis, onychomycosis, and selected Candida infections. Itraconazole inhibits fungal lanosterol 14α-demethylase (CYP51), disrupting ergosterol biosynthesis and impairing fungal cell membrane function. It is highly lipophilic, and its oral absorption depends strongly on the formulation. Important clinical considerations include numerous CYP3A4-mediated drug interactions, hepatotoxicity, and negative inotropic effects that can worsen heart failure

CAS Number: 84625-61-6

Molecular Mass: 705.6 g/mol

Formula: C₃₅H₃₈Cl₂N₈O₄

Smiles: CCC(C)n1ncn(-c2ccc(N3CCN(c4ccc(OCC5COC(Cn6cncn6)(c6ccc(Cl)cc6Cl)O5)cc4)CC3)cc2)c1=O

Synonymes:

Itraconazole, Itrizole, 2-butan-2-yl-4-[4-[4-[4-[[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, 2-butan-2-yl-4-(4-(4-(4-((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, RefChem:1048319, 1-(Butan-2-yl)-4-{4-[4-(4-{[2-(2,4-dichlorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one, 2049588-24-9, Itraconazolum [Latin], MLS000863291, C35H38Cl2N8O4, MFCD00870168, 1217512-35-0, SMR000058959, 4-(4-(4-(4-((2-((1H-1,2,4-triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-(sec-butyl)-1H-1,2,4-triazol-5(4H)-one, Itraconazole D3, 2-butan-2-yl-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-1,2,4-triazol-3-one, 4-(4-(4-(4-((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, SR-01000003153, Itraconzaole, NCGC00018268-03, 252964-65-1, 84604-65-9, ITRAZOLE, 2-[(1,1,1-~2~H_3_)Butan-2-yl]-4-(4-{4-[4-({2-(2,4-dichlorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]-1,3-dioxolan-4-yl}methoxy)phenyl]piperazin-1-yl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, Itraconazole (racemate), Opera_ID_902, Itraconazole Impurity 79, SCHEMBL95627, MLS000028582, MLS000759472, MLS001148245, MLS001424065, CHEMBL64391, Itraconazole, >=98% (TLC), SCHEMBL16984893, CHEBI:94366, Itraconazole - Bio-X trade mark, ARD14876D3, HMS2051K14, HMS2090M20, HMS2235M11, HMS3370P13, HMS3393K14, HMS3713B16, HMS5087A14, SYB51038, BDBM50011478, DL-427, EBC-46200, NSC754771, STL450986, AKOS000280875, AKOS022171690, CCG-100876, CCG-220567, FI24742, NC00126, NSC-754771, NCGC00018268-02, NCGC00018268-05, NCGC00018268-06, NCGC00018268-08, NCGC00018268-14, NCGC00089812-03, BI164594, DA-54483, CS-0242228, I0732, EN300-246240, O11835, AB00383031-14, SR-01000003153-5, SR-01000003153-6, Q27166205, Z2194031989, Itraconazole, European Pharmacopoeia (EP) Reference Standard, Itraconazole, United States Pharmacopeia (USP) Reference Standard, Itraconazole for system suitability, European Pharmacopoeia (EP) Reference Standard, Itraconazole, Pharmaceutical Secondary Standard, Certified Reference Material, (+/-)-cis-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]-methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-3h-1,2,4-triazol-3-one, 2-(butan-2-yl)-4-{4-[4-(4-{[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-[[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, rel-4-[4-[4-[4-[[(2R,4R)-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phen yl]-2,4-dihydro-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one

Bioactivity: Triazole antifungal agent; fungal lanosterol 14α-demethylase (CYP51) inhibitor; ergosterol biosynthesis inhibitor

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	288.15	-	0.1107	[156]
1-Butanol	293.15	-	0.1403	[156]
1-Butanol	298.15	-	0.1749	[156]
1-Butanol	298.15	-	0.176	[158]
1-Butanol	303.15	-	0.2191	[156]
1-Butanol	308.15	-	0.2675	[156]
1-Propanol	288.15	-	0.1176	[156]
1-Propanol	293.15	-	0.1519	[156]
1-Propanol	298.15	-	0.1962	[156]
1-Propanol	298.15	-	0.1925	[158]
1-Propanol	303.15	-	0.2504	[156]
1-Propanol	308.15	-	0.3123	[156]
Acetone	298.15	-	6.078	[158]
Acetonitrile	298.15	-	1.062	[158]
Chloroform	288.15	-	425.9	[156]
Chloroform	293.15	-	444.0	[156]
Chloroform	298.15	-	462.9	[156]
Chloroform	298.15	-	463.9	[158]
Chloroform	303.15	-	481.2	[156]
Chloroform	308.15	-	500.1	[156]
Dichloromethane	288.15	-	327.7	[156]
Dichloromethane	293.15	-	347.8	[156]
Dichloromethane	298.15	-	368.6	[156]
Dichloromethane	298.15	-	369.7	[158]
Dichloromethane	303.15	-	390.3	[156]
Dichloromethane	308.15	-	412.9	[156]
Diethylene Glycol Monoethyl Ether	298.15	-	3.78	[158]
Dimethyl sulfoxide	283.15	-	1.844	[157]
Dimethyl sulfoxide	288.15	-	2.362	[157]
Dimethyl sulfoxide	293.15	-	3.075	[157]
Dimethyl sulfoxide	298.15	-	3.871	[157]
Dimethyl sulfoxide	298.15	-	17.34	[158]
Dimethyl sulfoxide	303.15	-	4.617	[157]
Dimethyl sulfoxide	308.15	-	5.682	[157]
Dimethyl sulfoxide	313.15	-	6.907	[157]
Dimethyl sulfoxide	318.15	-	8.637	[157]
Dimethyl sulfoxide	323.15	-	10.37	[157]
Dimethylacetamide	298.15	-	90.55	[158]
Dimethylformamide	298.15	-	98.61	[158]
Ethanol	283.15	-	0.0841	[157]
Ethanol	288.15	-	0.13	[156]
Ethanol	288.15	-	0.1135	[157]
Ethanol	293.15	-	0.1729	[156]
Ethanol	293.15	-	0.152	[157]
Ethanol	298.15	-	0.2274	[156]
Ethanol	298.15	-	0.1999	[157]
Ethanol	298.15	-	0.2298	[158]
Ethanol	303.15	-	0.2918	[156]
Ethanol	303.15	-	0.2582	[157]
Ethanol	308.15	-	0.3782	[156]
Ethanol	308.15	-	0.3362	[157]
Ethanol	313.15	-	0.4416	[157]
Ethanol	318.15	-	0.5917	[157]
Ethanol	323.15	-	0.7436	[157]
Isopropanol	283.15	-	0.0774	[157]
Isopropanol	288.15	-	0.0967	[157]
Isopropanol	293.15	-	0.1198	[157]
Isopropanol	298.15	-	0.1442	[157]
Isopropanol	298.15	-	0.1963	[158]
Isopropanol	303.15	-	0.1841	[157]
Isopropanol	308.15	-	0.2247	[157]
Isopropanol	313.15	-	0.2727	[157]
Isopropanol	318.15	-	0.3277	[157]
Isopropanol	323.15	-	0.3897	[157]
Methanol	283.15	-	0.2896	[157]
Methanol	288.15	-	0.4118	[156]
Methanol	288.15	-	0.3759	[157]
Methanol	293.15	-	0.5174	[156]
Methanol	293.15	-	0.489	[157]
Methanol	298.15	-	0.6546	[156]
Methanol	298.15	-	0.6411	[157]
Methanol	298.15	-	0.6563	[158]
Methanol	303.15	-	0.8107	[156]
Methanol	303.15	-	0.8433	[157]
Methanol	308.15	-	1.006	[156]
Methanol	308.15	-	1.056	[157]
Methanol	313.15	-	1.323	[157]
Methanol	318.15	-	1.639	[157]
Methanol	323.15	-	2.02	[157]
N-Methyl-2-pyrrolidone	298.15	-	165.0	[158]
Tetrahydrofuran	298.15	-	18.34	[158]
Water	283.15	-	2.0 × 10⁻⁴	[157]
Water	288.15	-	3.0 × 10⁻⁴	[157]
Water	293.15	-	4.0 × 10⁻⁴	[157]
Water	298.15	-	6.0 × 10⁻⁴	[157]
Water	298.15	-	0.00949	[158]
Water	303.15	-	0.001	[157]
Water	308.15	-	0.0014	[157]
Water	313.15	-	0.0022	[157]
Water	318.15	-	0.0032	[157]
Water	323.15	-	0.0047	[157]

Molecule 3D descriptors

Descriptor	Value
PMI1	2349.4767
PMI2	47500.2096
PMI3	48127.7856
NPR1	0.0488
NPR2	0.9870
RadiusOfGyration	8.3321
InertialShapeFactor	0.0004
Eccentricity	0.9988
Asphericity	0.8614
SpherocityIndex	0.0721
PBF	1.0644