VORICONAZOLE

Search structure
Trade Names:
Synonyms:
Status: Approved (2002)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J02AC03
UNII: JFU09I87TR

Structure
InChI Key BCEHBSKCWLPMDN-MGPLVRAMSA-N
Smile C[C@@H](c1ncncc1F)[C@](O)(Cn1cncn1)c1ccc(F)cc1F
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H14F3N5O
Molecular Weight 349.32
AlogP 2.18
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 76.72
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 25.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Cytochrome P450 51 inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- - - - 25
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2A Cytochrome P450 2A6
- - - - 25
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2B Cytochrome P450 2B6
- 790-17500 - 340-400 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 5250-8700 - 5100 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- - - - 25
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 3620-8400 - 2800 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- - - - 25
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 13000 - 660-2970 -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A5
- 2900 - 660-2970 -
Enzyme Cytochrome P450 Cytochrome P450 family 51 Cytochrome P450 family 51A Cytochrome P450 51A1
- - 423-429 - -
Enzyme Oxidoreductase
- 2900 - 660-2970 -
Enzyme
- 790-17500 423-429 340-400 25

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Mycoses 3 D009181 ClinicalTrials
Neuroaspergillosis 3 D020953 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Candidiasis, Invasive 3 D058365 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Aspergillosis, Allergic Bronchopulmonary 2 D001229 ClinicalTrials
Neutropenia 1 D009503 ClinicalTrials
Hematologic Neoplasms 1 D019337 ClinicalTrials
Keratitis 1 D007634 ClinicalTrials
Graft vs Host Disease 1 D006086 ClinicalTrials
Asthma 1 D001249 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 1 D015451 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Investigations Blood creatinine increased 31.9
Eye disorders Visual impairment 28.1
Renal and urinary disorders Renal impairment 21.6
Eye disorders Visual impairment 20.6
General disorders and administration site conditions Chills 19.5
Metabolism and nutrition disorders Hypokalaemia 19.5
Eye disorders Visual impairment 18.7
Gastrointestinal disorders Nausea 15.7
Eye disorders Visual impairment 15.5
Investigations Body temperature increased 13.5
Eye disorders Visual impairment 13.5
Metabolism and nutrition disorders Hypokalaemia 12.2
Gastrointestinal disorders Vomiting 9.73
Investigations Blood creatinine increased 7.63
Gastrointestinal disorders Nausea 7.14
Renal and urinary disorders Renal impairment 6.87
Skin and subcutaneous tissue disorders Dermatitis 6.63
Skin and subcutaneous tissue disorders Rash 6.63
Investigations Body temperature increased 6.23
General disorders and administration site conditions Chills 6.11
Renal failure acute 5.95
Gastrointestinal disorders Nausea 5.89
Skin and subcutaneous tissue disorders Dermatitis 5.76
Skin and subcutaneous tissue disorders Rash 5.76
Investigations Body temperature increased 5.7
Investigations Body temperature increased 5.68
Gastrointestinal disorders Vomiting 5.61
Metabolism and nutrition disorders Hypomagnesaemia 5.41
Gastrointestinal disorders Nausea 5.4
Gastrointestinal disorders Nausea 5.38
Renal failure acute 5.34
Skin and subcutaneous tissue disorders Dermatitis 5.32
Skin and subcutaneous tissue disorders Rash 5.32
Skin and subcutaneous tissue disorders Dermatitis 5.3
Skin and subcutaneous tissue disorders Rash 5.3
Psychiatric disorders Hallucination 5.1
Investigations Blood alkaline phosphatase increased 5.0
Cardiac disorders Oedema peripheral 4.86
Gastrointestinal disorders Vomiting 4.76
Investigations Liver function test abnormal 4.59
Gastrointestinal disorders Vomiting 4.4
Gastrointestinal disorders Vomiting 4.35
Nervous system disorders Headache 4.32
Skin and subcutaneous tissue disorders Dermatitis 4.27
Skin and subcutaneous tissue disorders Rash 4.27
Eye disorders Visual impairment 4.19
General disorders and administration site conditions Chills 4.09
Investigations Blood alkaline phosphatase increased 4.06
Investigations Aspartate aminotransferase increased 4.0
Gastrointestinal disorders Nausea 3.85
Investigations Body temperature increased 3.82
Skin and subcutaneous tissue disorders Dermatitis 3.78
Skin and subcutaneous tissue disorders Rash 3.78
General disorders and administration site conditions Chills 3.7
General disorders and administration site conditions Chills 3.69
Investigations Blood alkaline phosphatase increased 3.62
Investigations Body temperature increased 3.57
Nervous system disorders Headache 3.57
Investigations Hepatic enzyme increased 3.57
Cardiac disorders Oedema peripheral 3.57
Eye disorders Photophobia 3.57
Investigations Blood alkaline phosphatase increased 3.56
Gastrointestinal disorders Abdominal pain 3.24
Gastrointestinal disorders Diarrhoea 3.24
Gastrointestinal disorders Gastrointestinal pain 3.24
Nervous system disorders Headache 3.22
Investigations Liver function test abnormal 3.21
Gastrointestinal disorders Vomiting 3.21
Investigations Blood alkaline phosphatase increased 3.06
Investigations Alanine aminotransferase increased 3.0
Nervous system disorders Headache 3.0
Investigations Liver function test abnormal 3.0
Nervous system disorders Headache 2.96
Psychiatric disorders Hallucination 2.78
Investigations Liver function test abnormal 2.75
Investigations Liver function test abnormal 2.72
Blood and lymphatic system disorders Anaemia 2.7
Investigations Hepatic enzyme increased 2.7
Investigations Liver function test abnormal 2.7
Cardiac disorders Tachycardia 2.7
Gastrointestinal disorders Abdominal pain 2.55
Cardiac disorders Dizziness 2.55
Gastrointestinal disorders Gastrointestinal pain 2.55
Cardiac disorders Tachycardia 2.55
Eye disorders Photophobia 2.5
Psychiatric disorders Hallucination 2.48
Cardiac disorders Tachycardia 2.48
Eye disorders Photophobia 2.41
Psychiatric disorders Hallucination 2.4
Cardiac disorders Tachycardia 2.4
Psychiatric disorders Hallucination 2.36
Cardiac disorders Tachycardia 2.36
Investigations Hepatic enzyme increased 2.35
Investigations Blood alkaline phosphatase increased 2.29
Eye disorders Photophobia 2.24
Investigations Blood alkaline phosphatase increased 2.16
Investigations Liver function test abnormal 2.16
Cardiac disorders Chest pain 2.04
Hepatobiliary disorders Jaundice cholestatic 2.04
Renal and urinary disorders Renal impairment 2.04
Vascular disorders Hypertension 1.94
Investigations Alanine aminotransferase increased 1.92
Investigations Aspartate aminotransferase increased 1.92
Nervous system disorders Headache 1.92
Investigations Aspartate aminotransferase increased 1.88
Investigations Hepatic enzyme increased 1.88
Investigations Aspartate aminotransferase increased 1.87
Investigations Alanine aminotransferase increased 1.81
Investigations Hepatic enzyme increased 1.81
Investigations Alanine aminotransferase increased 1.75
Vascular disorders Hypotension 1.74
Investigations Body temperature increased 1.71
Hepatobiliary disorders Jaundice cholestatic 1.71
Eye disorders Photophobia 1.71
Gastrointestinal disorders Abdominal pain 1.67
Gastrointestinal disorders Gastrointestinal pain 1.67
Blood and lymphatic system disorders Hyperbilirubinaemia 1.62
Vascular disorders Hypotension 1.62
Metabolism and nutrition disorders Hypokalaemia 1.61
Investigations Blood alkaline phosphatase increased 1.57
Metabolism and nutrition disorders Hypokalaemia 1.57
Gastrointestinal disorders Nausea 1.57
Investigations Alanine aminotransferase increased 1.53
Gastrointestinal disorders Diarrhoea 1.53
Gastrointestinal disorders Dry mouth 1.53
Blood and lymphatic system disorders Hyperbilirubinaemia 1.53
Gastrointestinal disorders Nausea 1.53
Skin and subcutaneous tissue disorders Dermatitis 1.5
Investigations Hepatic enzyme increased 1.5
Hepatobiliary disorders Jaundice cholestatic 1.5
Skin and subcutaneous tissue disorders Rash 1.5
Skin and subcutaneous tissue disorders Rash maculo-papular 1.5
Eye disorders Chromatopsia 1.34
Cardiac disorders Dizziness 1.34
Renal and urinary disorders Renal impairment 1.28
Cardiac disorders Tachycardia 1.28
Eye disorders Chromatopsia 1.21
Skin and subcutaneous tissue disorders Rash maculo-papular 1.14
Cardiac disorders Chest pain 1.08
Vascular disorders Hypertension 1.08
Skin and subcutaneous tissue disorders Pruritus 1.08
Blood and lymphatic system disorders Thrombocytopenia 1.08
Gastrointestinal disorders Diarrhoea 1.07
Blood and lymphatic system disorders Hyperbilirubinaemia 1.07
Metabolism and nutrition disorders Hypomagnesaemia 1.07
Hepatobiliary disorders Jaundice cholestatic 1.07
Cardiac disorders Oedema peripheral 1.07
Skin and subcutaneous tissue disorders Pruritus 1.07
Investigations Alanine aminotransferase increased 1.05
Investigations Aspartate aminotransferase increased 1.05
Cardiac disorders Dizziness 1.05
Investigations Liver function test abnormal 1.05
Eye disorders Photophobia 1.05
Hepatobiliary disorders Jaundice cholestatic 1.03
Eye disorders Chromatopsia 1.02
Metabolism and nutrition disorders Hypomagnesaemia 1.02
Skin and subcutaneous tissue disorders Pruritus 1.02
Blood and lymphatic system disorders Thrombocytopenia 1.02
Eye disorders Chromatopsia 1.0
Gastrointestinal disorders Dry mouth 1.0
Gastrointestinal disorders Nausea 1.0
Gastrointestinal disorders Vomiting 1.0
Blood and lymphatic system disorders Hyperbilirubinaemia 0.906
Cardiac disorders Chest pain 0.871
Blood and lymphatic system disorders Hyperbilirubinaemia 0.804
Investigations Aspartate aminotransferase increased 0.763
Skin and subcutaneous tissue disorders Dermatitis 0.763
Nervous system disorders Headache 0.763
Investigations Hepatic enzyme increased 0.763
Hepatobiliary disorders Jaundice cholestatic 0.763
Investigations Liver function test abnormal 0.763
Skin and subcutaneous tissue disorders Rash 0.763
Gastrointestinal disorders Vomiting 0.763
Metabolism and nutrition disorders Hypokalaemia 0.641
Renal and urinary disorders Renal impairment 0.604
Investigations Alanine aminotransferase increased 0.541
Psychiatric disorders Hallucination 0.541
Eye disorders Visual impairment 0.541
Renal and urinary disorders Renal impairment 0.536
Skin and subcutaneous tissue disorders Dermatitis 0.524
Gastrointestinal disorders Dry mouth 0.524
Nervous system disorders Headache 0.524
Skin and subcutaneous tissue disorders Rash 0.524
Renal and urinary disorders Renal impairment 0.524
Blood and lymphatic system disorders Thrombocytopenia 0.524
Gastrointestinal disorders Vomiting 0.524
Investigations Aspartate aminotransferase increased 0.51
Blood and lymphatic system disorders Hyperbilirubinaemia 0.51
Vascular disorders Hypertension 0.51
Metabolism and nutrition disorders Hypokalaemia 0.51
Vascular disorders Hypotension 0.51
Blood and lymphatic system disorders Leukopenia 0.51
Skin and subcutaneous tissue disorders Rash maculo-papular 0.51
Investigations Blood creatinine increased 0.5
General disorders and administration site conditions Chills 0.5
Blood and lymphatic system disorders Hyperbilirubinaemia 0.5
Vascular disorders Hypotension 0.5
Blood and lymphatic system disorders Jaundice 0.5
Cardiac disorders Oedema peripheral 0.5
Renal and urinary disorders Renal impairment 0.5
Renal failure acute 0.469
Blood and lymphatic system disorders Thrombocytopenia 0.469
Eye disorders Chromatopsia 0.427
Renal failure acute 0.427
Renal failure acute 0.423
Investigations Blood creatinine increased 0.268
Blood and lymphatic system disorders Leukopenia 0.268
Investigations Blood creatinine increased 0.242
General disorders and administration site conditions Chills 0.214
Eye disorders Eye haemorrhage 0.201
Blood and lymphatic system disorders Jaundice 0.201
Blood and lymphatic system disorders Anaemia 0.134
Blood and lymphatic system disorders Pancytopenia 0.067

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
16.44
Nervous system disorders
9.66
Infections and infestations
7.92
Respiratory, thoracic and mediastinal disorders
7.21
Injury, poisoning and procedural complications
6.97
Skin and subcutaneous tissue disorders
6.76
Investigations
6.28
Psychiatric disorders
5.57
Eye disorders
4.22
Gastrointestinal disorders
3.73
Musculoskeletal and connective tissue disorders
3.19
Vascular disorders
3.15
Metabolism and nutrition disorders
3.06
Cardiac disorders
2.94
Hepatobiliary disorders
2.73
Blood and lymphatic system disorders
2.57
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.53

Cross References

Resources Reference
CAS NUMBER 137234-62-9
ChEBI 10023
ChEMBL CHEMBL638
DrugBank DB00582
DrugCentral 2846
EPA CompTox DTXSID5046485
FDA SRS JFU09I87TR
Human Metabolome Database HMDB0014720
KEGG C07622
PDB VOR
PharmGKB PA10233
PubChem 71616
SureChEMBL SCHEMBL36233
ZINC ZINC000000014864
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