VORICONAZOLE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H14F3N5O
Molecular Weight	349.3111
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]([H])(c1c(cncn1)F)[C@](Cn2cncn2)(c3ccc(cc3F)F)O

InChI

InChIKey=BCEHBSKCWLPMDN-MGPLVRAMSA-N

InChI=1S/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H14F3N5O
Molecular Weight	349.3111
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/021466lbl.pdf
Curator's Comment:: description was created based on several sources, including: http://www.drugbank.ca/drugs/DB00582

Voriconazole (vor-i-KON-a-zole, brand name Vfend, Pfizer) is a triazole antifungal medication. VFEND® (voriconazole) is available as film-coated tablets for oral administration, and as a lyophilized powder for solution for intravenous infusion. Voriconazole is a triazole antifungal agent indicated for use in the treatment of fungal infections including invasive aspergillosis, esophageal candidiasis, and serious fungal infections caused by Scedosporium apiospermum (asexual form of Pseudallescheria boydii) and Fusarium spp. including Fusarium solani. Fungal plasma membranes are similar to mammalian plasma membranes, differing in having the nonpolar sterol ergosterol, rather than cholesterol, as the principal sterol. Membrane sterols such as ergosterol provide structure, modulation of membrane fluidity, and possibly control of some physiologic events. Voriconazole effects the formation of the fungal plasma membrane by indirectly inhibiting the biosynthesis of ergosterol. This results in plasma membrane permeability changes and inhibition of growth. The primary mode of action of voriconazole is the inhibition of fungal cytochrome P-450-mediated 14 alpha-lanosterol demethylation, an essential step in fungal ergosterol biosynthesis. The accumulation of 14 alpha-methyl sterols correlates with the subsequent loss of ergosterol in the fungal cell wall and may be responsible for the antifungal activity of voriconazole. Voriconazole has been shown to be more selective for fungal cytochrome P-450 enzymes than for various mammalian cytochrome P-450 enzyme systems. The most common side effects associated with voriconazole include transient visual disturbances, fever, rash, vomiting, nausea, diarrhea, headache, sepsis, peripheral edema, abdominal pain, and respiratory disorder. Unlike most adverse effects, which are similar to other azole antifungal agents, visual disturbances (such as blurred vision or increased sensitivity to light) are unique to voriconazole. Though rare, there have been cases of serious hepatic reactions during treatment with voriconazole (a class effect of azole antifungal agents). Liver function tests should be evaluated at the start of and during the course of therapy. Voriconazole is phototoxic. It has been associated with an increased risk of squamous-cell carcinoma of the skin

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 51 26 Target ID: CHEMBL1780 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/021466lbl.pdf	Inhibitor 7687

Conditions

Condition	Modality	Highest Phase	Product
Invasive aspergillosis 12 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/021466lbl.pdf	Curative	Approved 7968	VFEND Approved Use use in the treatment of the fungal infections Launch Date 1.07084159E12
Esophageal candidiasis 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/021466lbl.pdf	Curative	Approved 7968	VFEND Approved Use use in the treatment of the fungal infections Launch Date 1.07084159E12
Scedosporium apiospermum infection 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/021466lbl.pdf	Curative	Approved 7968	VFEND Approved Use use in the treatment of the fungal infections Launch Date 1.07084159E12
Fusarium spp. 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/021466lbl.pdf	Curative	Approved 7968	VFEND Approved Use use in the treatment of the fungal infections Launch Date 1.07084159E12

C_max

Value	Dose	Analyte	Population
3.13 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	6 mg/kg single, intravenous dose: 6 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2.31 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.03 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	3 mg/kg 2 times / day steady-state, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.77 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	4 mg/kg 2 times / day steady-state, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.74 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2.3 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933807	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	VORICONAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
13.9 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	6 mg/kg single, intravenous dose: 6 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
12.4 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
13.7 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	3 mg/kg 2 times / day steady-state, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
33.9 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	4 mg/kg 2 times / day steady-state, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
34 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
9.31 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
27.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933807	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	VORICONAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
15.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19933807	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		VORICONAZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
42% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
42% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021266s039,021267s050,021630s029lbl.pdf	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:		VORICONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
16 mg/kg 1 times / day steady, oral Recommended Dose: 16 mg/kg, 1 times / day Route: oral Route: steady Dose: 16 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/	unhealthy, 17 years n = 1 Health Status: unhealthy Condition: cystic fibrosis and allergic bronchopulmonary aspergillosis Age Group: 17 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/	Disc. AE: Photophobia, Fatigue... AEs leading to discontinuation/dose reduction: Photophobia (1 patient) Fatigue (1 patient) Concentration impaired (1 patient) Insomnia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/
200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/	unhealthy, 42.7–64.5 years n = 327 Health Status: unhealthy Condition: Acute myeloid leukemia, lymphocytic leukemia, Myelodysplastic syndrome, Multiple myeloma Lymphoma and Other Age Group: 42.7–64.5 years Sex: M+F Population Size: 327 Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/	Disc. AE: Function liver abnormal, Hallucination, visual... AEs leading to discontinuation/dose reduction: Function liver abnormal (73 patients) Hallucination, visual (16 patients) Skin rash (6 patients) Kidney dysfunction (3 patients) Electrocardiogram QTc interval prolonged (2 patients) Gastrointestinal symptom NOS (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/
400 mg single, oral Overdose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/30306637/	unhealthy, 53.4–67.5 years n = 31 Health Status: unhealthy Condition: Acute myeloid leukemia, Acute lymphoid leukemia, Lymphoma, Others Age Group: 53.4–67.5 years Sex: M+F Population Size: 31 Sources: https://pubmed.ncbi.nlm.nih.gov/30306637/	Disc. AE: CRP increased, Bilirubin increased... AEs leading to discontinuation/dose reduction: CRP increased (31 patient) Bilirubin increased (31 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/30306637/
16 mg/kg 1 times / day steady, oral Recommended Dose: 16 mg/kg, 1 times / day Route: oral Route: steady Dose: 16 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/	unhealthy, 9 years n = 1 Health Status: unhealthy Condition: cystic fibrosis and invasive aspergillosis Age Group: 9 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/	Disc. AE: Photophobia... AEs leading to discontinuation/dose reduction: Photophobia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/

AEs

AE	Significance	Dose	Population
Concentration impaired	1 patient Disc. AE	16 mg/kg 1 times / day steady, oral Recommended Dose: 16 mg/kg, 1 times / day Route: oral Route: steady Dose: 16 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/	unhealthy, 17 years n = 1 Health Status: unhealthy Condition: cystic fibrosis and allergic bronchopulmonary aspergillosis Age Group: 17 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/
Fatigue	1 patient Disc. AE	16 mg/kg 1 times / day steady, oral Recommended Dose: 16 mg/kg, 1 times / day Route: oral Route: steady Dose: 16 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/	unhealthy, 17 years n = 1 Health Status: unhealthy Condition: cystic fibrosis and allergic bronchopulmonary aspergillosis Age Group: 17 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/
Insomnia	1 patient Disc. AE	16 mg/kg 1 times / day steady, oral Recommended Dose: 16 mg/kg, 1 times / day Route: oral Route: steady Dose: 16 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/	unhealthy, 17 years n = 1 Health Status: unhealthy Condition: cystic fibrosis and allergic bronchopulmonary aspergillosis Age Group: 17 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/
Photophobia	1 patient Disc. AE	16 mg/kg 1 times / day steady, oral Recommended Dose: 16 mg/kg, 1 times / day Route: oral Route: steady Dose: 16 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/	unhealthy, 17 years n = 1 Health Status: unhealthy Condition: cystic fibrosis and allergic bronchopulmonary aspergillosis Age Group: 17 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/
Gastrointestinal symptom NOS	1 patient Disc. AE	200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/	unhealthy, 42.7–64.5 years n = 327 Health Status: unhealthy Condition: Acute myeloid leukemia, lymphocytic leukemia, Myelodysplastic syndrome, Multiple myeloma Lymphoma and Other Age Group: 42.7–64.5 years Sex: M+F Population Size: 327 Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/
Hallucination, visual	16 patients Disc. AE	200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/	unhealthy, 42.7–64.5 years n = 327 Health Status: unhealthy Condition: Acute myeloid leukemia, lymphocytic leukemia, Myelodysplastic syndrome, Multiple myeloma Lymphoma and Other Age Group: 42.7–64.5 years Sex: M+F Population Size: 327 Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/
Electrocardiogram QTc interval prolonged	2 patients Disc. AE	200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/	unhealthy, 42.7–64.5 years n = 327 Health Status: unhealthy Condition: Acute myeloid leukemia, lymphocytic leukemia, Myelodysplastic syndrome, Multiple myeloma Lymphoma and Other Age Group: 42.7–64.5 years Sex: M+F Population Size: 327 Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/
Kidney dysfunction	3 patients Disc. AE	200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/	unhealthy, 42.7–64.5 years n = 327 Health Status: unhealthy Condition: Acute myeloid leukemia, lymphocytic leukemia, Myelodysplastic syndrome, Multiple myeloma Lymphoma and Other Age Group: 42.7–64.5 years Sex: M+F Population Size: 327 Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/
Skin rash	6 patients Disc. AE	200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/	unhealthy, 42.7–64.5 years n = 327 Health Status: unhealthy Condition: Acute myeloid leukemia, lymphocytic leukemia, Myelodysplastic syndrome, Multiple myeloma Lymphoma and Other Age Group: 42.7–64.5 years Sex: M+F Population Size: 327 Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/
Function liver abnormal	73 patients Disc. AE	200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/	unhealthy, 42.7–64.5 years n = 327 Health Status: unhealthy Condition: Acute myeloid leukemia, lymphocytic leukemia, Myelodysplastic syndrome, Multiple myeloma Lymphoma and Other Age Group: 42.7–64.5 years Sex: M+F Population Size: 327 Sources: https://pubmed.ncbi.nlm.nih.gov/32171012/
Bilirubin increased	31 patient Disc. AE	400 mg single, oral Overdose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/30306637/	unhealthy, 53.4–67.5 years n = 31 Health Status: unhealthy Condition: Acute myeloid leukemia, Acute lymphoid leukemia, Lymphoma, Others Age Group: 53.4–67.5 years Sex: M+F Population Size: 31 Sources: https://pubmed.ncbi.nlm.nih.gov/30306637/
CRP increased	31 patient Disc. AE	400 mg single, oral Overdose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/30306637/	unhealthy, 53.4–67.5 years n = 31 Health Status: unhealthy Condition: Acute myeloid leukemia, Acute lymphoid leukemia, Lymphoma, Others Age Group: 53.4–67.5 years Sex: M+F Population Size: 31 Sources: https://pubmed.ncbi.nlm.nih.gov/30306637/
Photophobia	1 patient Disc. AE	16 mg/kg 1 times / day steady, oral Recommended Dose: 16 mg/kg, 1 times / day Route: oral Route: steady Dose: 16 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/	unhealthy, 9 years n = 1 Health Status: unhealthy Condition: cystic fibrosis and invasive aspergillosis Age Group: 9 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/27313918/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1469 inhibitor 1171	substrate 865 inhibitor 1318	substrate 1038

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1215 P-gp 1087 BCRP 574 BSEP 363 UGT2B 2	CYP2C19 830 CYP1A2 892 CYP2E1 567

Drug as perpetrator

Target	Modality	Activity
UGT2B 2	inhibitor 2612 Sources: https://pubmed.ncbi.nlm.nih.gov/23653047/ Page: 17.0	likely
BCRP 639	inhibitor 2612 Sources: https://pubmed.ncbi.nlm.nih.gov/17518356/	no
BSEP 364	inhibitor 2612 Sources: https://pubmed.ncbi.nlm.nih.gov/27001813/	no
CYP2C19 1277	inhibitor 2612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 12, 13, 14	yes [Ki 14 uM]
CYP3A4 1461	inhibitor 2612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 12, 13, 14	yes [Ki 22 uM]
CYP2C9 1362	inhibitor 2612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 12, 13, 14	yes [Ki 7 uM]
P-gp 1253	inhibitor 2612 Sources: https://pubmed.ncbi.nlm.nih.gov/23084335/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2C19 830	substrate 2751 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/021630s000_Vfend_ClinPharm.pdf Page: 2, 10,13, 21-23, 26-27	major	yes (co-administration study) Comment: from FDA label pp26-28: rifampin decreased voriconazole Cmax by 93% and AUC by 96% and fluconazole increased voriconazole Cmax by 57% and AUC 79% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/021630s000_Vfend_ClinPharm.pdf Page: 2, 10,13, 21-23, 26-27
CYP1A2 892	substrate 2751 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 12.0	no
CYP2D6 1038	substrate 2751 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 12.0	no
CYP2E1 567	substrate 2751 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 12.0	no
CYP2C9 865	substrate 2751 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 11.0	yes [Km 21 uM]	yes (co-administration study) Comment: from FDA label pp26-28: rifampin decreased voriconazole Cmax by 93% and AUC by 96%; fluconazole increased voriconazole Cmax by 57% and AUC 79% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 11.0
CYP3A4 1469	substrate 2751 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 11.0	yes [Km 240 uM]	yes (co-administration study) Comment: from FDA label pp26-28: rifampin decreased voriconazole Cmax by 93% and AUC by 96%; fluconazole increased voriconazole Cmax by 57% and AUC 79% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 11.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:10023	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:10023
ChemicalBook	CB01123117	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB01123117
ChemicalBook	CB1160110	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1160110
MolPort	MolPort-003-850-863	https://www.molport.com/shop/molecule-link/MolPort-003-850-863
Selleck Chemicals	Voriconazole	http://www.selleckchem.com/products/Voriconazole.html
ZINC	ZINC000000014864	http://zinc15.docking.org/substances/ZINC000000014864
eMolecules	30100386	https://www.emolecules.com/cgi-bin/more?vid=30100386
eMolecules	30487979	https://www.emolecules.com/cgi-bin/more?vid=30487979
eMolecules	902682	https://www.emolecules.com/cgi-bin/more?vid=902682

PubMed

Title	Date	PubMed
Improving the outcome of invasive aspergillosis: new diagnostic tools and new therapeutic strategies.	2002	12611078
Pharmacological aspects of the new triazole voriconazole.	2002	12611077
Successful treatment of Candida glabrata myocarditis with voriconazole.	2002	12477337
Voriconazole: in the treatment of invasive aspergillosis.	2002	12466006
Successful treatment of Paecilomyces lilacinus endophthalmitis with voriconazole.	2002	12374371
Influence of voriconazole and fluconazole on Candida albicans in long-time continuous flow culture.	2002	12073562
Gateways to Clinical Trials.	2002 Apr	12087878
Voriconazole versus amphotericin B for primary therapy of invasive aspergillosis.	2002 Aug 8	12167683
Use of voriconazole to successfully treat disseminated Trichosporon asahii infection in a patient with acute myeloid leukaemia.	2002 Dec	12525928
Usefulness of a colorimetric method for testing antifungal drug susceptibilities of Aspergillus species to voriconazole.	2002 Dec	12525904
Voriconazole in the management of invasive aspergillosis in two patients with acute myeloid leukemia undergoing stem cell transplantation.	2002 Dec	12476292
Case Reports. Chronic and acute Aspergillus meningitis.	2002 Dec	12472730
Voriconazole versus amphotericin B for invasive aspergillosis.	2002 Dec 19	12494937
Voriconazole versus amphotericin B for invasive aspergillosis.	2002 Dec 19	12490695
In vitro activity of three new triazoles and one echinocandin against Candida bloodstream isolates from cancer patients.	2002 Jul	12096017
Fungal keratitis caused by Scedosporium apiospermum: report of two cases and review of treatment.	2002 Jul	12072730
Severe keratomycosis secondary to Scedosporium apiospermum.	2002 Jul	12072729
Antifungal triazoles and polymorphonuclear leukocytes synergize to cause increased hyphal damage to Scedosporium prolificans and Scedosporium apiospermum.	2002 Jul	12069979
Voriconazole.	2002 Jul 22	12138377
Effect of medium composition on static and cidal activity of amphotericin B, itraconazole, voriconazole, posaconazole and terbinafine against Aspergillus fumigatus: a multicenter study.	2002 Jun	12120878
Invasive Aspergillus infections in hematologic malignancy patients.	2002 Jun	12070828
New drugs, old drugs - dear drugs, cheap drugs.	2002 Jun 15	12362279
Broth medium for microdilution susceptibility tests of fluconazole and voriconazole.	2002 May	12072930
Voriconazole versus liposomal amphotericin B for empirical antifungal therapy.	2002 May 30	12041527
Voriconazole versus liposomal amphotericin B for empirical antifungal therapy.	2002 May 30	12041526
Voriconazole versus liposomal amphotericin B for empirical antifungal therapy.	2002 May 30	12037157
Voriconazole -- better chances for patients with invasive mycoses.	2002 May 31	12069915
Management of mycoses in patients with hematologic disease and cancer -- review of the literature.	2002 May 31	12069913
Management of mycoses in surgical patients -- review of the literature.	2002 May 31	12069912
Gateways to clinical trials.	2002 Nov	12616707
In vitro susceptibilities of cerebrospinal fluid isolates of Cryptococcus neoformans collected during a ten-year period against fluconazole, voriconazole and posaconazole (SCH56592).	2002 Nov	12421285
An unusual case of pulmonary invasive aspergillosis and aspergilloma cured with voriconazole in a patient with cystic fibrosis.	2002 Nov 1	12384856
The safety of voriconazole.	2002 Nov 15	12410490
[Antifungal treatments].	2002 Nov 30	12497718
In vitro activities of investigational triazoles against Fusarium species: effects of inoculum size and incubation time on broth microdilution susceptibility test results.	2002 Oct	12234865
Voriconazole treatment of disseminated paecilomyces infection in a patient with acquired immunodeficiency syndrome.	2002 Oct 1	12228840
Pseudallescheria boydii (Anamorph Scedosporium apiospermum). Infection in solid organ transplant recipients in a tertiary medical center and review of the literature.	2002 Sep	12352630
Cerebral aspergillosis caused by Neosartorya hiratsukae, Brazil.	2002 Sep	12194781
Determination of voriconazole in aqueous humor by liquid chromatography-electrospray ionization-mass spectrometry.	2002 Sep 5	12138003
Emergence of nosocomial candidemia at a teaching hospital in Taiwan from 1981 to 2000: increased susceptibility of Candida species to fluconazole.	2002 Winter	12523628
Characterization of a lanosterol 14 alpha-demethylase from Pneumocystis carinii.	2003 Aug	12606318
Successful control of disseminated Scedosporium prolificans infection with a combination of voriconazole and terbinafine.	2003 Feb	12627286
In vitro activity of voriconazole, itraconazole, caspofungin, anidulafungin (VER002, LY303366) and amphotericin B against aspergillus spp.	2003 Feb	12614985
Antifungal pharmacotherapy for invasive mould infections.	2003 Feb	12562305
Disseminated infection due to Cylindrocarpon (Fusarium) lichenicola in a neutropenic patient with acute leukaemia: report of a case and review of the literature.	2003 Jan	12582748
In vitro activities of voriconazole, posaconazole, and four licensed systemic antifungal agents against Candida species infrequently isolated from blood.	2003 Jan	12517829
Activity of voriconazole against corneal isolates of Scedosporium apiospermum.	2003 Jan	12502945
In vitro susceptibilities of zygomycetes to conventional and new antifungals.	2003 Jan	12493786
Arthritis and osteomyelitis due to Aspergillus fumigatus: a 17 years old boy with chronic granulomatous disease.	2003 Jan 31	12605719
Voriconazole: a new triazole antifungal agent.	2003 Mar 1	12594645

Patents

Sample Use Guides

In Vivo Use Guide

Tablets should be taken at least one hour before, or one hour following, a meal.

Route of Administration: Oral

In Vitro Use Guide

each microdilution well containing 100 ul of the drug concentrations was inoculated with 100 ul of the diluted inoculum suspension (final volume in each well was 200 ul). Drug concentrations were 0.03 to 16 mg/ml for voriconazole. Stock inoculum suspensions of the molds were prepared from 7-day (Aspergillus spp., Bipolaris spp., P. boydii, R. arrhizus, and S. schenckii) or 7- to 10-day (B. dermatitidis and H. capsulatum) cultures grown on PDA at 35°C (cultures for Fusarium spp. were grown at 35°C for 48 to 72 h and then at 25 to 28°C until day 7

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:08:32 UTC 2021` Edited by `admin` on `Fri Jun 25 21:08:32 UTC 2021`
Record UNII	JFU09I87TR
Record Status	`Validated (UNII)`
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Name

Type

Language

VORICONAZOLE

Official Name

English

4-PYRIMIDINEETHANOL, A-(2,4-DIFLUOROPHENYL)-5-FLUORO-.BETA.-METHYL-.ALPHA.-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-, (.ALPHA.R,.BETA.S)-

Common Name

English

VORICONAZOLE [ORANGE BOOK]

Common Name

English

UK-109,496

Code

English

VORICONAZOLE [INN]

Common Name

English

UK-109496

Code

English

(.ALPHA.R,.BETA.S)-A-(2,4-DIFLUOROPHENYL)-5-FLUORO-.BETA.-METHYL-.ALPHA.-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-4-PYRIMIDINEETHANOL

Common Name

English

VORICONAZOLE [JAN]

Common Name

English

VORICONAZOLE [WHO-DD]

Common Name

English

VORICONAZOLE [USP-RS]

Common Name

English

VFEND

Brand Name

English

NSC-759888

Code

English

VORICONAZOLE [MART.]

Common Name

English

VORICONAZOLE [EMA EPAR]

Common Name

English

VORICONAZOLE [MI]

Common Name

English

VORICONAZOLE [USAN]

Common Name

English

VORICONAZOLE [EP MONOGRAPH]

Common Name

English

VORICONAZOLE [USP MONOGRAPH]

Common Name

English

VORICONAZOLE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C514