ITRACONAZOLE

Search structure
Trade Names:
Synonyms:
Status: Approved (1992)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J02AC02
UNII: 304NUG5GF4

Structure
InChI Key VHVPQPYKVGDNFY-UHFFFAOYSA-N
Smile CCC(C)n1ncn(-c2ccc(N3CCN(c4ccc(OCC5COC(Cn6cncn6)(c6ccc(Cl)cc6Cl)O5)cc4)CC3)cc2)c1=O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C35H38Cl2N8O4
Molecular Weight 705.65
AlogP 5.58
Hydrogen Bond Acceptor 12.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 11.0
Polar Surface Area 104.7
Molecular species NEUTRAL
Aromatic Rings 5.0
Heavy Atoms 49.0

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 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 33-700 - - 0-84
Enzyme Cytochrome P450 Cytochrome P450 family 51 Cytochrome P450 family 51A Cytochrome P450 51A1
- 3600 31 - -
Enzyme Protease Cysteine protease Cysteine protease CA clan Cysteine protease C1A family
- 3000 - - -
Enzyme
- 33-700 1010 - 0-84
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CC chemokine receptor
- 200-12589 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CXC chemokine receptor
- 100-20800 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Vasopressin and oxytocin receptor
- 794-12589 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 18000-18000 - - 2

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Mycoses 4 D009181 ClinicalTrials
Candidiasis 4 D002177 ClinicalTrials
Blastomycosis 4 D001759 ClinicalTrials
Cryptococcosis 3 D003453 ClinicalTrials
Histoplasmosis 3 D006660 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Sinusitis 2 D012852 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Carcinoma, Basal Cell 2 D002280 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Aspergillosis, Allergic Bronchopulmonary 2 D001229 ClinicalTrials
Meningitis, Cryptococcal 2 D016919 ClinicalTrials
Mycetoma 2 D008271 ClinicalTrials
Hematologic Diseases 2 D006402 ClinicalTrials
Tinea Pedis 2 D014008 ClinicalTrials
Tinea Versicolor 2 D014010 ClinicalTrials
Burns 2 D002056 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Lung Neoplasms 2 D008175 ClinicalTrials
Coccidioidomycosis 2 D003047 ClinicalTrials
Carcinoma, Basal Cell 2 D002280 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Cachexia 1 D002100 ClinicalTrials
Heart Failure 1 D006333 ClinicalTrials
Inflammatory Bowel Diseases 1 D015212 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Infections 1 D007239 ClinicalTrials
Muscular Atrophy, Spinal 1 D009134 ClinicalTrials
Neoplasm Metastasis 1 D009362 ClinicalTrials
Respiratory Syncytial Virus Infections 1 D018357 ClinicalTrials
Hepatitis B, Chronic 1 D019694 ClinicalTrials
Myelodysplastic Syndromes 1 D009190 ClinicalTrials
Hepatitis B, Chronic 1 D019694 ClinicalTrials
Celiac Disease 1 D002446 ClinicalTrials
Thrombosis 1 D013927 ClinicalTrials
Hepatitis C, Chronic 1 D019698 ClinicalTrials
Polycystic Ovary Syndrome 1 D011085 ClinicalTrials
Lymphoma 1 D008223 ClinicalTrials
Multiple Myeloma 1 D009101 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Cystic Fibrosis 1 D003550 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Asthma 1 D001249 ClinicalTrials
Alzheimer Disease 1 D000544 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 1 D029424 ClinicalTrials
Sporotrichosis 1 D013174 ClinicalTrials
Neuralgia 1 D009437 ClinicalTrials
Esophageal Neoplasms 0 D004938 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Chills 34.0
Metabolism and nutrition disorders Hypokalaemia 29.0
Metabolism and nutrition disorders Hypokalaemia 28.0
Investigations Blood creatinine increased 26.0
Investigations Blood creatinine increased 25.0
Gastrointestinal disorders Nausea 15.0
Gastrointestinal disorders Gastrointestinal disorder 12.3
Renal and urinary disorders Renal impairment 12.0
Gastrointestinal disorders Diarrhoea 11.0
Gastrointestinal disorders Nausea 11.0
Renal and urinary disorders Renal impairment 11.0
Respiratory, thoracic and mediastinal disorders Cough 10.0
Gastrointestinal disorders Diarrhoea 10.0
Gastrointestinal disorders Nausea 10.0
Gastrointestinal disorders Vomiting 10.0
Skin and subcutaneous tissue disorders Dermatitis 9.0
Gastrointestinal disorders Diarrhoea 9.0
Blood and lymphatic system disorders Hyperbilirubinaemia 9.0
Metabolism and nutrition disorders Hypokalaemia 9.0
Gastrointestinal disorders Nausea 9.0
Skin and subcutaneous tissue disorders Rash 9.0
Investigations Body temperature increased 8.0
Metabolism and nutrition disorders Hypokalaemia 8.0
Gastrointestinal disorders Nausea 8.0
Gastrointestinal disorders Vomiting 8.0
Infections and infestations Upper respiratory tract infection
Gastrointestinal disorders Abdominal pain 7.0
Investigations Blood urea increased 7.0
Investigations Body temperature increased 7.0
Gastrointestinal disorders Gastrointestinal pain 7.0
Gastrointestinal disorders Vomiting 7.0
Gastrointestinal disorders Abdominal pain 6.0
Investigations Blood urea increased 6.0
Investigations Body temperature increased 6.0
Skin and subcutaneous tissue disorders Dermatitis 6.0
Gastrointestinal disorders Diarrhoea 6.0
Gastrointestinal disorders Gastrointestinal pain 6.0
Nervous system disorders Headache 6.0
Blood and lymphatic system disorders Hyperbilirubinaemia 6.0
General disorders and administration site conditions Hyperhidrosis 6.0
Skin and subcutaneous tissue disorders Rash 6.0
Infections and infestations Upper respiratory tract infection 6.0
Gastrointestinal disorders Vomiting 6.0
Gastrointestinal disorders Nausea 5.3
Investigations Body temperature increased 5.0
Skin and subcutaneous tissue disorders Dermatitis 5.0
Cardiac disorders Dyspnoea 5.0
Metabolism and nutrition disorders Hypokalaemia 5.0
Metabolism and nutrition disorders Hypomagnesaemia 5.0
Gastrointestinal disorders Nausea 5.0
Skin and subcutaneous tissue disorders Rash 5.0
Gastrointestinal disorders Vomiting 5.0
Gastrointestinal disorders Diarrhoea 4.5
Gastrointestinal disorders Abdominal pain 4.0
General disorders and administration site conditions Application site reaction 4.0
Respiratory, thoracic and mediastinal disorders Cough 4.0
Skin and subcutaneous tissue disorders Dermatitis 4.0
Gastrointestinal disorders Diarrhoea 4.0
Cardiac disorders Dizziness 4.0
Gastrointestinal disorders Gastrointestinal disorder 4.0
Gastrointestinal disorders Gastrointestinal pain 4.0
Nervous system disorders Headache 4.0
Investigations Hepatic enzyme increased 4.0
Blood and lymphatic system disorders Hyperbilirubinaemia 4.0
General disorders and administration site conditions Hyperhidrosis 4.0
Metabolism and nutrition disorders Hypomagnesaemia 4.0
General disorders and administration site conditions Oedema 4.0
General disorders and administration site conditions Pain 4.0
Skin and subcutaneous tissue disorders Rash 4.0
Infections and infestations Sinusitis 4.0
Gastrointestinal disorders Vomiting 4.0
Gastrointestinal disorders Vomiting 3.4
Ear and labyrinth disorders Deafness 3.3
Hearing impaired 3.3
Ear and labyrinth disorders Deafness
Gastrointestinal disorders Diarrhoea
Hearing impaired
Gastrointestinal disorders Abdominal pain 3.0
Investigations Alanine aminotransferase increased 3.0
General disorders and administration site conditions Asthenia 3.0
Investigations Blood alkaline phosphatase increased 3.0
Investigations Blood creatinine increased 3.0
Investigations Blood triglycerides increased 3.0
Investigations Body temperature increased 3.0
Cardiac disorders Chest pain 3.0
Gastrointestinal disorders Constipation 3.0
Skin and subcutaneous tissue disorders Dermatitis 3.0
Gastrointestinal disorders Diarrhoea 3.0
Cardiac disorders Dyspnoea 3.0
General disorders and administration site conditions Fatigue 3.0
Cardiac disorders Fluid overload 3.0
Gastrointestinal disorders Gastrointestinal pain 3.0
Nervous system disorders Headache 3.0
Hepatobiliary disorders Hepatic function abnormal 3.0
Blood and lymphatic system disorders Hyperbilirubinaemia 3.0
General disorders and administration site conditions Hyperhidrosis 3.0
Vascular disorders Hypertension 3.0
Metabolism and nutrition disorders Hypertriglyceridaemia 3.0
Metabolism and nutrition disorders Hypocalcaemia 3.0
Vascular disorders Hypotension 3.0
Respiratory, thoracic and mediastinal disorders Increased bronchial secretion 3.0
Skin and subcutaneous tissue disorders Pruritus 3.0
Skin and subcutaneous tissue disorders Rash 3.0
Respiratory, thoracic and mediastinal disorders Sputum increased 3.0
Cardiac disorders Tachycardia 3.0
Vascular disorders Vein disorder 3.0
Gastrointestinal disorders Vomiting 3.0
Investigations Hepatic enzyme increased 2.9
Gastrointestinal disorders Nausea 2.9
Gastrointestinal disorders Abdominal pain
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Discomfort
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Abdominal pain 2.5
Gastrointestinal disorders Gastrointestinal pain 2.5
Gastrointestinal disorders Abdominal pain 2.4
Gastrointestinal disorders Diarrhoea 2.4
Gastrointestinal disorders Gastrointestinal pain 2.4
Nervous system disorders Headache 2.2
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Abdominal pain 2.0
Investigations Alanine aminotransferase increased 2.0
Investigations Aspartate aminotransferase increased 2.0
General disorders and administration site conditions Asthenia 2.0
Investigations Blood alkaline phosphatase increased 2.0
Investigations Blood creatinine increased 2.0
Investigations Blood lactate dehydrogenase increased 2.0
Cardiac disorders Chest pain 2.0
Gastrointestinal disorders Constipation 2.0
Psychiatric disorders Depression 2.0
Cardiac disorders Dizziness 2.0
Cardiac disorders Dyspnoea 2.0
General disorders and administration site conditions Fatigue 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
Nervous system disorders Headache 2.0
Hepatobiliary disorders Hepatic function abnormal 2.0
General disorders and administration site conditions Hyperhidrosis 2.0
Vascular disorders Hypertension 2.0
Metabolism and nutrition disorders Hypocalcaemia 2.0
Metabolism and nutrition disorders Hypokalaemia 2.0
Metabolism and nutrition disorders Hypomagnesaemia 2.0
Respiratory, thoracic and mediastinal disorders Increased bronchial secretion 2.0
Blood and lymphatic system disorders Jaundice 2.0
General disorders and administration site conditions Oedema 2.0
General disorders and administration site conditions Pain 2.0
Infections and infestations Pneumocystis jirovecii infection 2.0
Infections and infestations Pneumonia 2.0
Infections and infestations Sinusitis 2.0
Skin and subcutaneous tissue disorders Skin disorder 2.0
Respiratory, thoracic and mediastinal disorders Sputum increased 2.0
Gastrointestinal disorders Abdominal pain 1.9
Gastrointestinal disorders Gastrointestinal pain 1.9
Gastrointestinal disorders Abdominal pain 1.7
Gastrointestinal disorders Diarrhoea 1.7
General disorders and administration site conditions Discomfort 1.7
Gastrointestinal disorders Gastrointestinal pain 1.7
Gastrointestinal disorders Nausea 1.7
Infections and infestations Bacteriuria
Skin and subcutaneous tissue disorders Dermatitis 1.6
Investigations Electrocardiogram abnormal
Nervous system disorders Headache
Nervous system disorders Headache 1.6
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 1.6
Nervous system disorders Nervous system disorder 1.6
Skin and subcutaneous tissue disorders Rash 1.6
General disorders and administration site conditions Asthenia 1.5
General disorders and administration site conditions Fatigue 1.5
Infections and infestations Bacteriuria 1.4
Investigations Electrocardiogram abnormal 1.4
Skin and subcutaneous tissue disorders Dermatitis 1.3
Nervous system disorders Headache 1.3
Skin and subcutaneous tissue disorders Pruritus 1.3
Skin and subcutaneous tissue disorders Rash 1.3
Musculoskeletal and connective tissue disorders Back pain 1.2
Respiratory, thoracic and mediastinal disorders Cough 1.2
Cardiac disorders Dizziness 1.2
Hepatobiliary disorders Hepatic function abnormal 1.2
Vascular disorders Hypotension 1.2
Gastrointestinal disorders Nausea 1.2
Immune system disorders Urticaria 1.2
Nervous system disorders Headache 1.1
Investigations Alanine aminotransferase increased 1.0
Renal and urinary disorders Albuminuria 1.0
Investigations Aspartate aminotransferase increased 1.0
General disorders and administration site conditions Asthenia 1.0
Investigations Blood alkaline phosphatase increased 1.0
Investigations Blood urea increased 1.0
General disorders and administration site conditions Chills 1.0
Gastrointestinal disorders Constipation 1.0
General disorders and administration site conditions Decreased appetite 1.0
Psychiatric disorders Depression 1.0
Skin and subcutaneous tissue disorders Dermatitis 1.0
General disorders and administration site conditions Discomfort 1.0
Psychiatric disorders Disturbance in sexual arousal 1.0
Cardiac disorders Dizziness 1.0
Gastrointestinal disorders Dysgeusia 1.0
Cardiac disorders Dyspnoea 1.0
Psychiatric disorders Erectile dysfunction 1.0
General disorders and administration site conditions Fatigue 1.0
General disorders and administration site conditions Feeling abnormal 1.0
Cardiac disorders Fluid overload 1.0
Nervous system disorders Headache 1.0
Hepatobiliary disorders Hepatic function abnormal 1.0
General disorders and administration site conditions Hyperhidrosis 1.0
Metabolism and nutrition disorders Hypocalcaemia 1.0
Metabolism and nutrition disorders Hypomagnesaemia 1.0
Vascular disorders Hypotension 1.0
General disorders and administration site conditions Ill-defined disorder 1.0
Respiratory, thoracic and mediastinal disorders Increased bronchial secretion 1.0
Blood and lymphatic system disorders Jaundice 1.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain 1.0
Psychiatric disorders Libido decreased 1.0
General disorders and administration site conditions Malaise 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.0
Musculoskeletal and connective tissue disorders Myalgia 1.0
General disorders and administration site conditions Oedema 1.0
Nervous system disorders Orthostatic hypotension 1.0
General disorders and administration site conditions Pain 1.0
Skin and subcutaneous tissue disorders Pruritus 1.0
Skin and subcutaneous tissue disorders Rash 1.0
Renal and urinary disorders Renal impairment 1.0
Cardiac disorders Sinus bradycardia 1.0
Skin and subcutaneous tissue disorders Skin disorder 1.0
Nervous system disorders Somnolence 1.0
Respiratory, thoracic and mediastinal disorders Sputum increased 1.0
Cardiac disorders Tachycardia 1.0
Infections and infestations Urinary tract infection 1.0
Immune system disorders Vasculitis 1.0
Ear and labyrinth disorders Vertigo 1.0
Gastrointestinal disorders Vomiting 1.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain
Infections and infestations Urinary tract infection

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
16.34
Injury, poisoning and procedural complications
7.62
Nervous system disorders
7.29
Gastrointestinal disorders
6.44
Investigations
6.24
Cardiac disorders
5.82
Infections and infestations
5.82
Respiratory, thoracic and mediastinal disorders
5.19
Skin and subcutaneous tissue disorders
5.13
Metabolism and nutrition disorders
4.77
Vascular disorders
4.51
Musculoskeletal and connective tissue disorders
3.64
Hepatobiliary disorders
3.4
Psychiatric disorders
3.2
Renal and urinary disorders
2.66
Blood and lymphatic system disorders
2.44

Cross References

Resources Reference
CAS NUMBER 84625-61-6
ChEBI 94366
ChEMBL CHEMBL64391
DrugCentral 1513
FDA SRS 304NUG5GF4
PubChem 55283
SureChEMBL SCHEMBL16984893
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