Itraconazole

Itraconazole
Clinical data
Trade names	Sporanox, Sporaz, Orungal, others
Other names	ITZ
AHFS/Drugs.com	Monograph
MedlinePlus	a692049
License data	US DailyMed: Itraconazole;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth, solution), vaginal suppository, intravenous
ATC code	J02AC02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	~55%, maximal if taken with full meal
Protein binding	99.8%
Metabolism	Extensive in liver (CYP3A4)
Metabolites	Hydroxy-itraconazole, keto-itraconazole,; N-desalkyl-itraconazole
Elimination half-life	21 hours
Excretion	Kidney (35%), faeces (54%)
Identifiers
	IUPAC name (±)-1-[(RS)-sec-butyl]-4-[p-[4-[p-[[(2R,4S)-rel-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-Δ2-1,2,4-triazolin-5-one;
CAS Number	84625-61-6 ;
PubChem CID	55283;
DrugBank	DB01167 ;
ChemSpider	49927 ;
UNII	304NUG5GF4;
KEGG	D00350 ;
ChEBI	CHEBI:6076 ;
ChEMBL	ChEMBL22587 ;
CompTox Dashboard (EPA)	DTXSID3023180 ;
ECHA InfoCard	100.123.596
Chemical and physical data
Formula	C35H38Cl2N8O4
Molar mass	705.64 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Melting point	165 °C (329 °F)
Solubility in water	7.8 ± 0.4 × 10−6 mol/L (pH 1.6) mg/mL (20 °C)
	SMILES O=C1N(/N=C\N1c2ccc(cc2)N7CCN(c6ccc(OC[C@@H]3O[C@](OC3)(c4ccc(Cl)cc4Cl)Cn5ncnc5)cc6)CC7)C(C)CC;
	InChI 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 ; Key:VHVPQPYKVGDNFY-ZPGVKDDISA-N ;
	(verify)

Itraconazole, sometimes abbreviated ITZ, is an antifungal medication used to treat a number of fungal infections. This includes aspergillosis, blastomycosis, coccidioidomycosis, histoplasmosis, and paracoccidioidomycosis. It may be given by mouth or intravenously.

Common side effects include nausea, diarrhea, abdominal pain, rash, and headache. Severe side effects may include liver problems, heart failure, Stevens–Johnson syndrome and allergic reactions including anaphylaxis. It is unclear if use during pregnancy or breastfeeding is safe. It is in the triazole family of medications. It stops fungal growth by affecting the cell membrane or affecting their metabolism.

Itraconazole was patented in 1978 and approved for medical use in the United States in 1992. It is on the World Health Organization's List of Essential Medicines.

Recent research works suggest itraconazole (ITZ) could also be used in the treatment of cancer by inhibiting the hedgehog pathway in a similar way to sonidegib.

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