Voriconazole

Azole Antifungal — ANTIINFECTIVES FOR SYSTEMIC USE

Key facts

Voriconazole is an ofp drug in the Azole Antifungal class catalogued in DrugCentral. It was first approved by the EMA in 2002. Its mechanism of action is classified as Cytochrome P450 2C19 Inhibitors, Cytochrome P450 2C9 Inhibitors and Cytochrome P450 3A4 Inhibitors. DrugCentral lists 12 molecular targets, including ERG11, CYP46A1 and Sterol 14-alpha-demethylase. Recorded indications include Candidemia, Candidiasis of the esophagus, Disseminated candidiasis and Fungal Infection due to Fusarium Solani.

• Approval status: ofp (first approved 2002 by the EMA).
• Drug class: Azole Antifungal.
• Mechanism of action: Cytochrome P450 2C19 Inhibitors; Cytochrome P450 2C9 Inhibitors; Cytochrome P450 3A4 Inhibitors.
• Molecular targets: ERG11, CYP46A1, Sterol 14-alpha-demethylase and cyp51A (12 listed in DrugCentral).
• Indications: Candidemia, Candidiasis of the esophagus, Disseminated candidiasis, Fungal Infection due to Fusarium Solani and Fungal Infection due to Scedosporium Apiospermum and others.
• ATC code: J02AC03 (Triazole and tetrazole derivatives).
• Molecular formula: C16H14F3N5O; molecular weight 349.32 g/mol.

Indications & contraindications

Drug–disease relationships curated by DrugCentral (OMOP / SNOMED concepts).

Indications (8)

• Candidemia
• Candidiasis of the esophagus
• Disseminated candidiasis
• Fungal Infection due to Fusarium Solani
• Fungal Infection due to Scedosporium Apiospermum
• Fusarium infection
• Invasive pulmonary aspergillosis
• Prophylaxis of invasive fungal infections in high risk allogeneic hematopoietic stem cell transplant (HSCT) recipients

Off-label uses (1)

• Oropharyngeal Candidiasis

Contraindications (13)

• Breastfeeding (mother)
• Cardiomyopathy
• Congenital long QT syndrome
• Disease of liver
• Hypocalcemia
• Hypokalemia
• Hypomagnesemia
• Impaired renal function disorder
• Poor metabolizer due to cytochrome p450 CYP2C19 variant
• Pregnancy, function
• Prolonged QT interval
• Torsades de pointes
• Visual impairment

Mechanism & targets

• Mechanism of action (MoA): Cytochrome P450 2C19 Inhibitors; Cytochrome P450 2C9 Inhibitors; Cytochrome P450 3A4 Inhibitors
• Established pharmacologic class: Azole Antifungal

Molecular targets (12)

Target	Gene	Action	Activity
Lanosterol 14-alpha demethylase	ERG11	inhibitor	MIC 8.73
Cholesterol 24-hydroxylase	CYP46A1	unknown	Ki 7.96
Sterol 14-alpha-demethylase	—	unknown	Kd 7.25
14-alpha sterol demethylase	cyp51A	unknown	Kd 7.25
14-alpha sterol demethylase	CYP51	unknown	Kd 7.25
14-alpha sterol demethylase	cyp51B	unknown	Kd 6.37
Lanosterol 14-alpha demethylase	cyp51	unknown	MIC 5.84
14-alpha sterol demethylase Cyp51A	—	unknown	Kd 5.44
Cytochrome P450 11A1	CYP11A1	unknown	Kd 5.32
Cytochrome P450 3A4	CYP3A4	unknown	IC50 4.89
Cytochrome P450 2C9	CYP2C9	unknown	IC50 4.85
Cytochrome P450 2C19	CYP2C19	unknown	IC50 4.82

Regulatory approvals (3)

Date	Agency	Marketed as	Applicant	Orphan
2005-04-11	PMDA	—	—
2002-05-24	FDA	—	PF PRISM CV
2002-03-19	EMA	—	—

ATC classification

ATC code	Therapeutic hierarchy
J02AC03	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIMYCOTICS FOR SYSTEMIC USE › ANTIMYCOTICS FOR SYSTEMIC USE › Triazole and tetrazole derivatives

Pharmacogenomics

Drug-label and guideline annotations from PharmGKB and CPIC.

• EMA label: CYP2C19 · Informative PGx
• FDA label: CYP2C19 · Informative PGx
• HCSC label: CYP2C19 · Informative PGx
• PMDA label: CYP2C19 · Actionable PGx
• Swissmedic label: CYP2C19 · Actionable PGx

Reported adverse-event signals

Strongest FDA FAERS disproportionality signals (log-likelihood ratio). A signal is a statistical association in spontaneous reports, not proof that the drug causes the event.

MedDRA term	LLR
Drug interaction	2063.1
Bronchopulmonary aspergillosis	1450.7
Aspergillus infection	1312.7
Drug ineffective	1288.8
Photosensitivity reaction	1265.9
Mucormycosis	1116.2
Periostitis	1035.3
Drug level increased	972.6
Multiple organ dysfunction syndrome	860.6
Drug resistance	811.6
Hallucination, visual	796.8
Actinic keratosis	744.2

Chemical structure

• Molecular formula: C₁₆H₁₄F₃N₅O
• Molecular weight: 349.32 g/mol
• CAS number: 137234-62-9
• InChIKey: BCEHBSKCWLPMDN-MGPLVRAMSA-N
• PubChem CID: 71616

C[C@@H](C1=NC=NC=C1F)[C@](O)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1

Frequently asked questions

Answers are generated from the structured data on this page, not written by hand.

What is Voriconazole used for?

DrugCentral lists the following indications for Voriconazole: Candidemia, Candidiasis of the esophagus, Disseminated candidiasis, Fungal Infection due to Fusarium Solani, Fungal Infection due to Scedosporium Apiospermum, Fusarium infection, Invasive pulmonary aspergillosis and Prophylaxis of invasive fungal infections in high risk allogeneic hematopoietic stem cell transplant (HSCT) recipients.

How does Voriconazole work?

Voriconazole is classified as Cytochrome P450 2C19 Inhibitors, Cytochrome P450 2C9 Inhibitors and Cytochrome P450 3A4 Inhibitors; its molecular targets in DrugCentral include ERG11 (inhibitor), CYP46A1, Sterol 14-alpha-demethylase and cyp51A.

When was Voriconazole first approved?

Voriconazole was first approved by the EMA in 2002.

What drug class does Voriconazole belong to?

Voriconazole is in the Azole Antifungal class.

What is the chemical formula of Voriconazole?

Voriconazole has the molecular formula C16H14F3N5O and a molecular weight of 349.32 g/mol.

Sources

• DrugCentral drug card 2846 — structure, indications, targets, approvals, pharmacologic classes (CC BY-SA 4.0)
• ChEMBL CHEMBL638 — compound record and bioactivity
• PubChem CID 71616 — chemical identifiers
• DrugBank DB00582 — drug record
• FDA UNII JFU09I87TR — substance identity
• DailyMed: FDA labels for Voriconazole — current prescribing information (label search)
• UniProt Q9Y6A2 (CYP46A1) — target protein
• UniProt P08684 (CYP3A4) — target protein
• UniProt P11712 (CYP2C9) — target protein
• UniProt P33261 (CYP2C19) — target protein
• FDA Adverse Event Reporting System (openFDA FAERS) — adverse-event signals, as aggregated by DrugCentral
• PharmGKB / CPIC — pharmacogenomic label annotations

How this page is built: methodology · editorial policy & corrections.