POSACONAZOLE

Search structure
Trade Names:
Synonyms:
Status: Approved (2006)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J02AC04
UNII: 6TK1G07BHZ

Structure
InChI Key RAGOYPUPXAKGKH-XAKZXMRKSA-N
Smile CC[C@@H]([C@H](C)O)n1ncn(-c2ccc(N3CCN(c4ccc(OC[C@@H]5CO[C@@](Cn6cncn6)(c6ccc(F)cc6F)C5)cc4)CC3)cc2)c1=O
InChI
InChI=1S/C37H42F2N8O4/c1-3-35(26(2)48)47-36(49)46(25-42-47)31-7-5-29(6-8-31)43-14-16-44(17-15-43)30-9-11-32(12-10-30)50-20-27-19-37(51-21-27,22-45-24-40-23-41-45)33-13-4-28(38)18-34(33)39/h4-13,18,23-27,35,48H,3,14-17,19-22H2,1-2H3/t26-,27+,35-,37-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C37H42F2N8O4
Molecular Weight 700.79
AlogP 4.57
Hydrogen Bond Acceptor 12.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 12.0
Polar Surface Area 115.7
Molecular species NEUTRAL
Aromatic Rings 5.0
Heavy Atoms 51.0

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 11 Cytochrome P450 family 11B Cytochrome P450 11B1
- 310 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 11 Cytochrome P450 family 11B Cytochrome P450 11B2
- 21 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 17 Cytochrome P450 family 17A Cytochrome P450 17A1
- 42-1800 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 19 Cytochrome P450 family 19A Cytochrome P450 19A1
- 8400 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 7200 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 50-672 - - 98
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A5
- - - - 98
Enzyme Cytochrome P450 Cytochrome P450 family 51 Cytochrome P450 family 51A Cytochrome P450 51A1
- - 131 - 93
Enzyme Oxidoreductase
- 48 18-60 - -
Enzyme
- 50-672 18-60 - 93
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- - - - 15
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 8100 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Coccidioidomycosis 3 D003047 ClinicalTrials
Mycoses 3 D009181 ClinicalTrials
Leukopenia 3 D007970 ClinicalTrials
Candidiasis, Oral 3 D002180 ClinicalTrials
Chagas Disease 2 D014355 ClinicalTrials
Granulomatous Disease, Chronic 2 D006105 ClinicalTrials
Leukemia 1 D007938 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Glioblastoma 0 D005909 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Investigations Body temperature increased 34.3
Gastrointestinal disorders Diarrhoea 32.0
Gastrointestinal disorders Diarrhoea 29.3
Gastrointestinal disorders Nausea 29.3
Gastrointestinal disorders Vomiting 28.0
Respiratory, thoracic and mediastinal disorders Cough 25.1
Metabolism and nutrition disorders Hypokalaemia 22.0
Investigations Body temperature increased 21.0
Nervous system disorders Headache 19.7
General disorders and administration site conditions Decreased appetite 19.2
Gastrointestinal disorders Nausea 19.0
Gastrointestinal disorders Abdominal pain 18.0
Gastrointestinal disorders Gastrointestinal pain 18.0
Nervous system disorders Insomnia 16.3
Blood and lymphatic system disorders Neutropenia 16.3
Skin and subcutaneous tissue disorders Dermatitis 15.1
Skin and subcutaneous tissue disorders Rash 15.1
Blood and lymphatic system disorders Anaemia 14.2
Investigations Weight decreased 13.8
General disorders and administration site conditions Asthenia 13.0
Investigations Body temperature increased 13.0
Gastrointestinal disorders Diarrhoea 13.0
General disorders and administration site conditions Fatigue 13.0
General disorders and administration site conditions Chills 12.1
Infections and infestations Candida infection 11.7
Cardiac disorders Dyspnoea 11.7
Gastrointestinal disorders Nausea 11.5
Metabolism and nutrition disorders Dehydration 11.3
General disorders and administration site conditions Pain 11.3
Infections and infestations Herpes simplex 10.9
Infections and infestations Pneumonia 10.5
Gastrointestinal disorders Diarrhoea 10.4
Blood and lymphatic system disorders Neutropenia 10.0
General disorders and administration site conditions Hyperhidrosis 9.62
Nervous system disorders Headache 8.78
Gastrointestinal disorders Nausea 8.62
Investigations Body temperature increased 8.4
Nervous system disorders Headache 8.0
Nervous system disorders Headache 7.9
Immune system disorders Acquired immunodeficiency syndrome 7.0
Immune system disorders Autoimmune disorder 7.0
Gastrointestinal disorders Vomiting 6.87
Gastrointestinal disorders Vomiting 6.64
Gastrointestinal disorders Abdominal pain 6.49
Gastrointestinal disorders Gastrointestinal pain 6.49
Investigations Body temperature increased 6.1
Nervous system disorders Headache 6.0
Gastrointestinal disorders Nausea 6.0
Blood and lymphatic system disorders Neutropenia 5.0
Gastrointestinal disorders Abdominal pain 4.85
Gastrointestinal disorders Gastrointestinal pain 4.85
General disorders and administration site conditions Asthenia 4.58
General disorders and administration site conditions Fatigue 4.58
Respiratory, thoracic and mediastinal disorders Cough 4.2
Skin and subcutaneous tissue disorders Dermatitis 4.17
Skin and subcutaneous tissue disorders Rash 4.17
Skin and subcutaneous tissue disorders Skin disorder 4.17
Skin and subcutaneous tissue disorders Dermatitis 3.82
Skin and subcutaneous tissue disorders Rash 3.82
Blood and lymphatic system disorders Neutropenia 3.77
General disorders and administration site conditions Asthenia 3.23
Respiratory, thoracic and mediastinal disorders Cough 3.23
General disorders and administration site conditions Fatigue 3.23
Cardiac disorders Dyspnoea 3.05
Infections and infestations Herpes simplex 3.05
Blood and lymphatic system disorders Neutropenia 3.05
Infections and infestations Pneumonia 3.05
Investigations Gamma-glutamyltransferase increased 2.99
Skin and subcutaneous tissue disorders Dermatitis 2.96
Metabolism and nutrition disorders Hypokalaemia 2.96
Metabolism and nutrition disorders Malnutrition 2.96
Skin and subcutaneous tissue disorders Rash 2.96
Skin and subcutaneous tissue disorders Skin disorder 2.96
Infections and infestations Herpes simplex 2.87
Skin and subcutaneous tissue disorders Dermatitis 2.69
Skin and subcutaneous tissue disorders Rash 2.69
Metabolism and nutrition disorders Dehydration 2.67
Investigations Aspartate aminotransferase increased 2.66
Investigations Hepatic enzyme increased 2.66
Blood and lymphatic system disorders Hyperbilirubinaemia 2.66
Investigations Gamma-glutamyltransferase increased 2.34
Investigations Hepatic enzyme increased 2.34
General disorders and administration site conditions Hyperhidrosis 2.33
Infections and infestations Pneumonia 2.29
Metabolism and nutrition disorders Hypokalaemia 2.08
Metabolism and nutrition disorders Malnutrition 2.08
Gastrointestinal disorders Abdominal pain 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
Investigations Hepatic enzyme increased 2.0
Gastrointestinal disorders Nausea 2.0
Gastrointestinal disorders Vomiting 2.0
Investigations Blood creatinine increased 1.99
Renal and urinary disorders Urethral disorder 1.99
Renal and urinary disorders Urinary tract disorder 1.99
Blood and lymphatic system disorders Anaemia 1.97
Blood and lymphatic system disorders Anaemia 1.91
General disorders and administration site conditions Asthenia 1.91
General disorders and administration site conditions Hyperhidrosis 1.91
General disorders and administration site conditions Decreased appetite 1.8
Skin and subcutaneous tissue disorders Dermatitis 1.72
Metabolism and nutrition disorders Hypokalaemia 1.72
Metabolism and nutrition disorders Malnutrition 1.72
Skin and subcutaneous tissue disorders Rash 1.72
Skin and subcutaneous tissue disorders Skin disorder 1.72
Investigations Blood alkaline phosphatase increased 1.67
Investigations Blood creatinine increased 1.67
Blood and lymphatic system disorders Hyperbilirubinaemia 1.67
Metabolism and nutrition disorders Malnutrition 1.67
Renal and urinary disorders Urethral disorder 1.67
Renal and urinary disorders Urinary tract disorder 1.67
Investigations Blood alkaline phosphatase increased 1.66
Metabolism and nutrition disorders Malnutrition 1.66
General disorders and administration site conditions Asthenia 1.62
General disorders and administration site conditions Chills 1.53
General disorders and administration site conditions Decreased appetite 1.53
Cardiac disorders Dyspnoea 1.44
Nervous system disorders Insomnia 1.44
Nervous system disorders Insomnia 1.15
Investigations Aspartate aminotransferase increased 1.0
Infections and infestations Pneumonia 1.0
General disorders and administration site conditions Pain 0.763
Investigations Weight decreased 0.763
Metabolism and nutrition disorders Dehydration 0.718
General disorders and administration site conditions Pain 0.718
Investigations Weight decreased 0.718
Infections and infestations Candida infection 0.539
Infections and infestations Candida infection 0.382
General disorders and administration site conditions Chills 0.359

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
16.71
Investigations
10.45
Injury, poisoning and procedural complications
9.04
Gastrointestinal disorders
8.47
Infections and infestations
8.03
Respiratory, thoracic and mediastinal disorders
5.84
Nervous system disorders
4.76
Blood and lymphatic system disorders
4.61
Metabolism and nutrition disorders
4.44
Vascular disorders
4.22
Skin and subcutaneous tissue disorders
3.51
Cardiac disorders
3.21
Hepatobiliary disorders
2.6
Musculoskeletal and connective tissue disorders
2.18
Renal and urinary disorders
2.01

Cross References

Resources Reference
CAS NUMBER 171228-49-2
ChEBI 64355
ChEMBL CHEMBL1397
DrugBank DB01263
DrugCentral 3483
FDA SRS 6TK1G07BHZ
KEGG D02555
PDB X2N
PubChem 468595
SureChEMBL SCHEMBL991747
ZINC ZINC000003938482
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