VORICONAZOLE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H14F3N5O
Molecular Weight	349.3105
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H](C1=C(F)C=NC=N1)[C@](O)(CN2C=NC=N2)C3=C(F)C=C(F)C=C3

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	349.3105
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 28 Target ID: CHEMBL1780 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/021466lbl.pdf	Inhibitor 8228

Conditions

Condition	Modality	Highest Phase	Product
Invasive aspergillosis 14 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/021466lbl.pdf	Curative	Approved 8360	VFEND Approved Use use in the treatment of the fungal infections Launch Date 1.07084159E12
Esophageal candidiasis 9 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/021466lbl.pdf	Curative	Approved 8360	VFEND Approved Use use in the treatment of the fungal infections Launch Date 1.07084159E12
Scedosporium apiospermum infection 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/021466lbl.pdf	Curative	Approved 8360	VFEND Approved Use use in the treatment of the fungal infections Launch Date 1.07084159E12
Fusarium spp. 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/021466lbl.pdf	Curative	Approved 8360	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 1709 inhibitor 1579	substrate 1010 inhibitor 1752	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1463 P-gp 1437 BCRP 691 BSEP 401 UGT2B 3	CYP2C19 985 CYP1A2 1032 CYP2E1 648

Drug as perpetrator

Target	Modality	Activity
UGT2B 3	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23653047/ Page: 17.0	likely
BCRP 765	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/17518356/	no
BSEP 402	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/27001813/	no
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 12, 13, 14	yes [Ki 14 uM]
CYP3A4 1909	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 12, 13, 14	yes [Ki 22 uM]
CYP2C9 1803	inhibitor 3240 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 1626	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23084335/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2C19 985	substrate 3326 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 1032	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 12.0	no
CYP2D6 1193	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 12.0	no
CYP2E1 648	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-266_VFEND_biopharmr.pdf Page: 12.0	no
CYP2C9 1010	substrate 3326 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 1709	substrate 3326 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
Antifungal activity of a new triazole, voriconazole (UK-109496), against clinical isolates of Aspergillus spp.	2000 Jun	11810544
Coccidioidomycosis: efficacy of new agents and future prospects.	2001 Dec	11964886
Aspergillus: rising frequency of clinical isolation and continued susceptibility to antifungal agents, 1994-1999.	2001 Dec	11777662
Muco-cutaneous retinoid-effects and facial erythema related to the novel triazole antifungal agent voriconazole.	2001 Nov	11722447
Effect of the growth medium on the in vitro antifungal activity of micafungin (FK-463) against clinical isolates of Candida dubliniensis.	2001 Nov	11679561
Development of azole resistance during fluconazole maintenance therapy for AIDS-associated cryptococcal disease.	2001 Nov 23	11698718
Improving the outcome of invasive aspergillosis: new diagnostic tools and new therapeutic strategies.	2002	12611078
Successful treatment of Paecilomyces lilacinus endophthalmitis with voriconazole.	2002	12374371
Six novel antimycotics.	2002	11893219
Diagnosis and treatment of invasive pulmonary aspergillosis in neutropenic patients.	2002 Apr	11999005
Recent advances in the epidemiology, prevention, diagnosis, and treatment of fungal pneumonia.	2002 Apr	11964921
Effect of voriconazole on the pharmacokinetics of cyclosporine in renal transplant patients.	2002 Apr	11956505
Safety and pharmacokinetics of oral voriconazole in patients at risk of fungal infection: a dose escalation study.	2002 Apr	11936564
Antifungal activities of posaconazole, ravuconazole, and voriconazole compared to those of itraconazole and amphotericin B against 239 clinical isolates of Aspergillus spp. and other filamentous fungi: report from SENTRY Antimicrobial Surveillance Program, 2000.	2002 Apr	11897586
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
Effect of granulocyte colony-stimulating factor and granulocyte-macrophage colony-stimulating factor on polymorphonuclear neutrophils, monocytes or monocyte-derived macrophages combined with voriconazole against Cryptococcus neoformans.	2002 Feb	11860010
The 2001 Garrod lecture. The treatment of cytomegalovirus infection.	2002 Feb	11815564
A multidrug, including voriconazole, resistant oral Candida infection in an AIDS patient effectively treated with echinocandin.	2002 Jan	11972427
Voriconazole versus liposomal amphotericin B in patients with neutropenia and persistent fever.	2002 Jan 24	11807157
Empirical antifungal therapy--new options, new tradeoffs.	2002 Jan 24	11807153
Voriconazole compared with liposomal amphotericin B for empirical antifungal therapy in patients with neutropenia and persistent fever.	2002 Jan 24	11807146
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
Antifungal triazoles and polymorphonuclear leukocytes synergize to cause increased hyphal damage to Scedosporium prolificans and Scedosporium apiospermum.	2002 Jul	12069979
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
E-test method for testing susceptibilities of Aspergillus spp. to the new triazoles voriconazole and posaconazole and to established antifungal agents: comparison with NCCLS broth microdilution method.	2002 Jun	12037072
In vitro activities of ravuconazole and voriconazole compared with those of four approved systemic antifungal agents against 6,970 clinical isolates of Candida spp.	2002 Jun	12019081
Voriconazole and fluconazole susceptibility of Candida isolates.	2002 Jun	12018654
New drugs, old drugs - dear drugs, cheap drugs.	2002 Jun 15	12362279
Voriconazole in the treatment of aspergillosis, scedosporiosis and other invasive fungal infections in children.	2002 Mar	12005089
Review of the safety and efficacy of voriconazole.	2002 Mar	11866669
Efficacy and safety of voriconazole in the treatment of acute invasive aspergillosis.	2002 Mar 1	11807679
[Antimycotic treatment of pulmonary aspergilloma in patients without neutropenia].	2002 Mar 8	11884987
Hypercalcemia induced by 13-cis-retinoic acid in a patient with neuroblastoma.	2002 May	12013365
Clinical evaluation of a frozen commercially prepared microdilution panel for antifungal susceptibility testing of seven antifungal agents, including the new triazoles posaconazole, ravuconazole, and voriconazole.	2002 May	11980944
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	12037157
Decisions about voriconazole versus liposomal amphotericin B.	2002 May 9	12000825
Gateways to clinical trials.	2002 Nov	12616707
[Antifungal treatments].	2002 Nov 30	12497718
Pseudallescheria boydii (Anamorph Scedosporium apiospermum). Infection in solid organ transplant recipients in a tertiary medical center and review of the literature.	2002 Sep	12352630
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
Successful control of disseminated Scedosporium prolificans infection with a combination of voriconazole and terbinafine.	2003 Feb	12627286
Antifungal pharmacotherapy for invasive mould infections.	2003 Feb	12562305
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
Arthritis and osteomyelitis due to Aspergillus fumigatus: a 17 years old boy with chronic granulomatous disease.	2003 Jan 31	12605719

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 `Wed Jul 05 23:20:34 UTC 2023` Edited by `admin` on `Wed Jul 05 23:20:34 UTC 2023`
Record UNII	JFU09I87TR
Record Status	`Validated (UNII)`
Record Version

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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 [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 [WHO-DD]

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