ATOVAQUONE

Search structure
Trade Names:
Synonyms:
Status: Approved (1992)
Entry Type: Small molecule
Molecule Category: Parent
ATC: P01AX06
UNII: Y883P1Z2LT

Structure
InChI Key KUCQYCKVKVOKAY-CTYIDZIISA-N
Smile O=C1C(O)=C([C@H]2CC[C@H](c3ccc(Cl)cc3)CC2)C(=O)c2ccccc21
InChI
InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,26H,5-8H2/t13-,15-

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H19ClO3
Molecular Weight 366.84
AlogP 5.51
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 2.0
Polar Surface Area 54.37
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 26.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Cytochrome b inhibitor PubMed DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 2600-14500 - - -
Enzyme
- 2600-14500 - 27000 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 82

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Malaria, Falciparum 3 D016778 ClinicalTrials
Toxoplasmosis, Cerebral 2 D016781 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Gastroesophageal Reflux 1 D005764 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 1 D002289 ClinicalTrials
Leukemia, Myeloid, Acute 0 D015470 ClinicalTrials

Related Entries

Scaffolds

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Skin and subcutaneous tissue disorders Dermatitis 46.0
Skin and subcutaneous tissue disorders Rash 46.0
Gastrointestinal disorders Diarrhoea 42.0
Investigations Body temperature increased 40.0
Skin and subcutaneous tissue disorders Dermatitis 39.0
Skin and subcutaneous tissue disorders Rash 39.0
Gastrointestinal disorders Nausea 37.0
Gastrointestinal disorders Nausea 36.6
Gastrointestinal disorders Diarrhoea 35.0
Gastrointestinal disorders Nausea 32.0
General disorders and administration site conditions Asthenia 31.0
Investigations Body temperature increased 31.0
Respiratory, thoracic and mediastinal disorders Cough 31.0
Gastrointestinal disorders Diarrhoea 31.0
Nervous system disorders Headache 31.0
Nervous system disorders Headache 28.2
Skin and subcutaneous tissue disorders Dermatitis 28.0
Nervous system disorders Headache 28.0
Skin and subcutaneous tissue disorders Rash 28.0
Gastrointestinal disorders Nausea 26.0
Investigations Body temperature increased 25.4
Investigations Body temperature increased 25.0
Respiratory, thoracic and mediastinal disorders Cough 25.0
Infections and infestations Rhinitis 24.0
Skin and subcutaneous tissue disorders Dermatitis 23.0
Gastrointestinal disorders Nausea 23.0
Skin and subcutaneous tissue disorders Rash 23.0
General disorders and administration site conditions Asthenia 22.0
Skin and subcutaneous tissue disorders Dermatitis 22.0
Nervous system disorders Headache 22.0
Infections and infestations Infection 22.0
Gastrointestinal disorders Nausea 22.0
Skin and subcutaneous tissue disorders Rash 22.0
Gastrointestinal disorders Vomiting 22.0
Gastrointestinal disorders Abdominal pain 21.0
Gastrointestinal disorders Diarrhoea 21.0
Cardiac disorders Dyspnoea 21.0
Gastrointestinal disorders Gastrointestinal pain 21.0
Gastrointestinal disorders Nausea 21.0
Gastrointestinal disorders Abdominal pain 20.0
Gastrointestinal disorders Gastrointestinal pain 20.0
Gastrointestinal disorders Diarrhoea 19.0
Infections and infestations Infection 19.0
Nervous system disorders Insomnia 19.0
Investigations Body temperature increased 18.0
Nervous system disorders Headache 18.0
Infections and infestations Infection 18.0
Infections and infestations Rhinitis 18.0
Infections and infestations Rhinitis 17.0
Gastrointestinal disorders Vomiting 17.0
Gastrointestinal disorders Vomiting 16.9
Skin and subcutaneous tissue disorders Dermatitis 16.1
Skin and subcutaneous tissue disorders Rash 16.1
Cardiac disorders Dyspnoea 16.0
Nervous system disorders Headache 16.0
Endocrine disorders Hypoglycaemia 15.5
Cardiac disorders Dyspnoea 15.0
Endocrine disorders Hypoglycaemia 15.0
Gastrointestinal disorders Vomiting 15.0
Cardiac disorders Dizziness 14.1
Nervous system disorders Insomnia 14.1
General disorders and administration site conditions Asthenia 14.0
Investigations Body temperature increased 14.0
Respiratory, thoracic and mediastinal disorders Cough 14.0
Cardiac disorders Dizziness 14.0
Nervous system disorders Insomnia 14.0
Gastrointestinal disorders Vomiting 14.0
Skin and subcutaneous tissue disorders Dermatitis 13.0
Gastrointestinal disorders Dysgeusia 13.0
Endocrine disorders Hyperglycaemia 13.0
Skin and subcutaneous tissue disorders Rash 13.0
Skin and subcutaneous tissue disorders Dermatitis 12.7
Gastrointestinal disorders Dysgeusia 12.7
Skin and subcutaneous tissue disorders Rash 12.7
Gastrointestinal disorders Abdominal pain 11.3
Gastrointestinal disorders Gastrointestinal pain 11.3
Gastrointestinal disorders Abdominal pain 11.0
Gastrointestinal disorders Gastrointestinal pain 11.0
Endocrine disorders Hypoglycaemia 11.0
Gastrointestinal disorders Vomiting 11.0
Gastrointestinal disorders Abdominal pain 10.0
Psychiatric disorders Anxiety 10.0
General disorders and administration site conditions Decreased appetite 10.0
Gastrointestinal disorders Dyspepsia 10.0
Gastrointestinal disorders Gastrointestinal pain 10.0
Metabolism and nutrition disorders Hyponatraemia 10.0
Vascular disorders Hypotension 10.0
Nervous system disorders Insomnia 10.0
General disorders and administration site conditions Pain 10.0
Psychiatric disorders Anxiety 9.86
General disorders and administration site conditions Decreased appetite 9.86
Gastrointestinal disorders Dyspepsia 9.86
Vascular disorders Hypotension 9.86
General disorders and administration site conditions Pain 9.86
Blood and lymphatic system disorders Anaemia 9.0
Endocrine disorders Hyperglycaemia 9.0
Blood and lymphatic system disorders Neutropenia 9.0
Gastrointestinal disorders Vomiting 9.0
Skin and subcutaneous tissue disorders Dermatitis 8.8
Skin and subcutaneous tissue disorders Rash 8.8
Investigations Amylase increased 8.0
General disorders and administration site conditions Asthenia 8.0
Investigations Blood alkaline phosphatase increased 8.0
Skin and subcutaneous tissue disorders Dermatitis 8.0
Cardiac disorders Dizziness 8.0
Skin and subcutaneous tissue disorders Rash 8.0
Skin and subcutaneous tissue disorders Dermatitis 7.6
Skin and subcutaneous tissue disorders Rash 7.6
Infections and infestations Rhinitis 7.04
Investigations Amylase increased 7.0
Psychiatric disorders Anxiety 7.0
Investigations Blood creatinine increased 7.0
General disorders and administration site conditions Decreased appetite 7.0
Metabolism and nutrition disorders Hyponatraemia 7.0
Infections and infestations Rhinitis 7.0
Infections and infestations Sinusitis 7.0
Skin and subcutaneous tissue disorders Dermatitis 6.3
Skin and subcutaneous tissue disorders Rash 6.3
Investigations Alanine aminotransferase increased 6.0
Blood and lymphatic system disorders Anaemia 6.0
Skin and subcutaneous tissue disorders Dermatitis 6.0
Skin and subcutaneous tissue disorders Rash 6.0
Infections and infestations Sinusitis 6.0
Infections and infestations Sinusitis 5.63
Investigations Body temperature increased 5.6
Investigations Aspartate aminotransferase increased 5.0
Gastrointestinal disorders Dyspepsia 5.0
Metabolism and nutrition disorders Hyperkalaemia 5.0
Blood and lymphatic system disorders Neutropenia 5.0
Skin and subcutaneous tissue disorders Pruritus 5.0
Infections and infestations Rhinitis 5.0
Immune system disorders Hypersensitivity 4.8
Gastrointestinal disorders Nausea 4.1
Gastrointestinal disorders Abdominal pain 4.0
Investigations Amylase increased 4.0
Blood and lymphatic system disorders Anaemia 4.0
Investigations Aspartate aminotransferase increased 4.0
Skin and subcutaneous tissue disorders Dermatitis 4.0
Gastrointestinal disorders Diarrhoea 4.0
Gastrointestinal disorders Gastrointestinal pain 4.0
Blood and lymphatic system disorders Leukopenia 4.0
Skin and subcutaneous tissue disorders Rash 4.0
Gastrointestinal disorders Diarrhoea 3.2
Gastrointestinal disorders Constipation 3.0
Cardiac disorders Dizziness 3.0
Gastrointestinal disorders Dysgeusia 3.0
Gastrointestinal disorders Nausea 3.0
Blood and lymphatic system disorders Neutropenia 3.0
Investigations Body temperature increased 2.9
Immune system disorders Hypersensitivity 2.9
Gastrointestinal disorders Nausea 2.5
Gastrointestinal disorders Vomiting 2.2
Gastrointestinal disorders Diarrhoea 2.1
Blood and lymphatic system disorders Anaemia 2.0
Immune system disorders Bronchospasm 2.0
Blood and lymphatic system disorders Anaemia 1.5
Respiratory, thoracic and mediastinal disorders Cough 1.41
Gastrointestinal disorders Vomiting 1.3
Immune system disorders Hypersensitivity 1.1
Respiratory, thoracic and mediastinal disorders Cough 1.0
Endocrine disorders Hypoglycaemia 1.0
Vascular disorders Hypotension 1.0
Gastrointestinal disorders Vomiting 1.0
Immune system disorders Hypersensitivity 0.8
Gastrointestinal disorders Nausea 0.8
Gastrointestinal disorders Vomiting 0.8
Investigations Body temperature increased 0.6
Gastrointestinal disorders Nausea 0.6
Gastrointestinal disorders Vomiting 0.6
Gastrointestinal disorders Diarrhoea 0.4
Gastrointestinal disorders Diarrhoea 0.2

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
12.74
Skin and subcutaneous tissue disorders
7.18
Infections and infestations
6.93
Blood and lymphatic system disorders
6.89
Gastrointestinal disorders
6.86
Respiratory, thoracic and mediastinal disorders
6.79
Injury, poisoning and procedural complications
6.17
Nervous system disorders
5.91
Investigations
5.59
Metabolism and nutrition disorders
5.37
Hepatobiliary disorders
3.92
Immune system disorders
3.81
Vascular disorders
3.45
Psychiatric disorders
2.9
Renal and urinary disorders
2.87
Musculoskeletal and connective tissue disorders
2.69
Surgical and medical procedures
2.5
Cardiac disorders
2.07

Cross References

Resources Reference
CAS NUMBER 95233-18-4
ChEBI 575568
ChEMBL CHEMBL1450
DrugBank DB01117
DrugCentral 258
EPA CompTox DTXSID7022629
FDA SRS Y883P1Z2LT
Human Metabolome Database HMDB0015249
Guide to Pharmacology 9695
KEGG C06835
PDB AOQ
SureChEMBL SCHEMBL21694
ZINC ZINC000116473771
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