RITONAVIR

Search structure
Trade Names:
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J05AE03
UNII: O3J8G9O825

Structure
InChI Key NCDNCNXCDXHOMX-XGKFQTDJSA-N
Smile CC(C)c1nc(CN(C)C(=O)N[C@H](C(=O)N[C@@H](Cc2ccccc2)C[C@H](O)[C@H](Cc2ccccc2)NC(=O)OCc2cncs2)C(C)C)cs1
InChI
InChI=1S/C37H48N6O5S2/c1-24(2)33(42-36(46)43(5)20-29-22-49-35(40-29)25(3)4)34(45)39-28(16-26-12-8-6-9-13-26)18-32(44)31(17-27-14-10-7-11-15-27)41-37(47)48-21-30-19-38-23-50-30/h6-15,19,22-25,28,31-33,44H,16-18,20-21H2,1-5H3,(H,39,45)(H,41,47)(H,42,46)/t28-,31-,32-,33-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C37H48N6O5S2
Molecular Weight 720.96
AlogP 5.91
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 17.0
Polar Surface Area 145.78
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 50.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Cytochrome P450 3A inhibitor FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2B Cytochrome P450 2B6
- 2000 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 12700 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 4900 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 2300 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 30-550 - 100-170 75-80
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A5
- - - 120 -
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A2A subfamily
- - 1-1 0-60 74-100
Enzyme Protease Cysteine protease Cysteine protease PAC clan Cysteine protease C3A subfamily
150 1-9850 - 0-1 72-90
Enzyme Transferase
- 1700-3000 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
4000 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 700-5000 - 1300 85
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 24800 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- 80-4400 - - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 1740-2200 - - 116
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 11100 - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hepatitis C 4 D006526 ClinicalTrials
Infections 3 D007239 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Acquired Immunodeficiency Syndrome 3 D000163 ClinicalTrials
Hepatitis D 3 D003699 ClinicalTrials
Mycobacterium avium-intracellulare Infection 2 D015270 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Pregnancy 2 D011247 ClinicalTrials
Coronavirus Infections 2 D018352 ClinicalTrials
Hepatitis B, Chronic 2 D019694 ClinicalTrials
Sarcoma, Kaposi 2 D012514 ClinicalTrials
Kidney Diseases 1 D007674 ClinicalTrials
Hypertension, Pulmonary 1 D006976 ClinicalTrials
Amyotrophic Lateral Sclerosis 1 D000690 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Hypertension 1 D006973 ClinicalTrials
Malaria 1 D008288 ClinicalTrials
Insulin Resistance 1 D007333 ClinicalTrials
Erectile Dysfunction 1 D007172 ClinicalTrials
Tuberculosis 1 D014376 ClinicalTrials
Liver Diseases 1 D008107 ClinicalTrials
Neoplasm Metastasis 1 D009362 ClinicalTrials
Respiratory Distress Syndrome 1 D012128 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture
Mixture
Mixture
Mixture
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Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Nausea 46.6
Gastrointestinal disorders Nausea 29.8
General disorders and administration site conditions Asthenia 28.4
General disorders and administration site conditions Asthenia 27.6
Gastrointestinal disorders Nausea 26.2
Gastrointestinal disorders Nausea 26.1
Gastrointestinal disorders Nausea 25.6
Gastrointestinal disorders Diarrhoea 25.0
Gastrointestinal disorders Nausea 24.4
Gastrointestinal disorders Diarrhoea 23.3
Gastrointestinal disorders Vomiting 23.3
Gastrointestinal disorders Nausea 23.1
Gastrointestinal disorders Vomiting 22.4
Gastrointestinal disorders Diarrhoea 21.6
Gastrointestinal disorders Diarrhoea 18.3
Gastrointestinal disorders Vomiting 17.4
Gastrointestinal disorders Dysgeusia 17.2
Gastrointestinal disorders Dysgeusia 15.5
Gastrointestinal disorders Diarrhoea 15.4
General disorders and administration site conditions Asthenia 15.3
Gastrointestinal disorders Vomiting 15.2
General disorders and administration site conditions Asthenia 14.2
Gastrointestinal disorders Vomiting 13.7
Gastrointestinal disorders Diarrhoea 12.8
Gastrointestinal disorders Vomiting 12.8
Gastrointestinal disorders Vomiting 12.6
General disorders and administration site conditions Asthenia 11.8
Gastrointestinal disorders Dysgeusia 11.1
General disorders and administration site conditions Asthenia 10.3
Gastrointestinal disorders Dysgeusia 10.3
General disorders and administration site conditions Asthenia 10.1
Social circumstances Fasting 9.9
General disorders and administration site conditions Asthenia 9.4
Blood and lymphatic system disorders Neutropenia 9.0
General disorders and administration site conditions Decreased appetite 8.6
Gastrointestinal disorders Dysgeusia 8.4
Gastrointestinal disorders Nausea
Gastrointestinal disorders Abdominal pain 8.3
Gastrointestinal disorders Gastrointestinal pain 8.3
Gastrointestinal disorders Diarrhoea
Social circumstances Fasting 7.9
General disorders and administration site conditions Decreased appetite 7.8
Nervous system disorders Headache 7.8
Gastrointestinal disorders Dysgeusia 7.6
Nervous system disorders Headache 7.6
Gastrointestinal disorders Abdominal pain 7.0
Gastrointestinal disorders Dysgeusia 7.0
Gastrointestinal disorders Gastrointestinal pain 7.0
Metabolism and nutrition disorders Hyperamylasaemia 7.0
Nervous system disorders Headache 6.7
Gastrointestinal disorders Paraesthesia oral 6.7
Nervous system disorders Headache 6.5
General disorders and administration site conditions Asthenia
Nervous system disorders Headache 6.3
General disorders and administration site conditions Decreased appetite 6.1
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Abdominal pain 6.0
Gastrointestinal disorders Gastrointestinal pain 6.0
Nervous system disorders Headache 6.0
Nervous system disorders Paraesthesia 6.0
Gastrointestinal disorders Abdominal pain 5.9
Gastrointestinal disorders Dyspepsia 5.9
Gastrointestinal disorders Gastrointestinal pain 5.9
Gastrointestinal disorders Paraesthesia oral 5.9
Nervous system disorders Headache
Gastrointestinal disorders Nausea
Gastrointestinal disorders Dysgeusia 5.4
General disorders and administration site conditions Asthenia
Gastrointestinal disorders Abdominal pain 5.2
General disorders and administration site conditions Discomfort 5.2
Cardiac disorders Dizziness 5.2
General disorders and administration site conditions Feeling abnormal 5.2
Gastrointestinal disorders Gastrointestinal pain 5.2
General disorders and administration site conditions Ill-defined disorder 5.2
General disorders and administration site conditions Malaise 5.2
Nervous system disorders Paraesthesia 5.2
Gastrointestinal disorders Paraesthesia oral 5.2
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
Nervous system disorders Headache 5.1
Investigations Body temperature increased 5.0
Nervous system disorders Paraesthesia 5.0
Blood and lymphatic system disorders Thrombocytopenia 5.0
Gastrointestinal disorders Dyspepsia 4.8
Investigations Body temperature increased 4.4
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Abdominal pain 4.3
General disorders and administration site conditions Discomfort 4.3
General disorders and administration site conditions Feeling abnormal 4.3
Gastrointestinal disorders Gastrointestinal pain 4.3
General disorders and administration site conditions Ill-defined disorder 4.3
General disorders and administration site conditions Malaise 4.3
Gastrointestinal disorders Abdominal pain 4.2
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 4.2
Gastrointestinal disorders Gastrointestinal pain 4.2
Blood and lymphatic system disorders Anaemia 4.0
Nervous system disorders Headache
Cardiac disorders Dizziness 3.9
Skin and subcutaneous tissue disorders Dermatitis 3.5
Skin and subcutaneous tissue disorders Rash 3.5
Gastrointestinal disorders Abdominal pain 3.4
Gastrointestinal disorders Constipation 3.4
General disorders and administration site conditions Decreased appetite 3.4
General disorders and administration site conditions Discomfort 3.4
Cardiac disorders Dizziness 3.4
General disorders and administration site conditions Feeling abnormal 3.4
Gastrointestinal disorders Gastrointestinal pain 3.4
General disorders and administration site conditions Hyperhidrosis 3.4
General disorders and administration site conditions Ill-defined disorder 3.4
Nervous system disorders Insomnia 3.4
General disorders and administration site conditions Malaise 3.4
Gastrointestinal disorders Paraesthesia oral 3.4
Surgical and medical procedures Vasodilation procedure 3.4
Cardiac disorders Dizziness 3.3
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
Investigations Aspartate aminotransferase increased 3.0
Nervous system disorders Paraesthesia 3.0
Gastrointestinal disorders Throat irritation 2.8
Gastrointestinal disorders Constipation 2.6
Skin and subcutaneous tissue disorders Dermatitis 2.6
Cardiac disorders Dizziness 2.6
Gastrointestinal disorders Dyspepsia 2.6
Gastrointestinal disorders Flatulence 2.6
General disorders and administration site conditions Hyperhidrosis 2.6
Nervous system disorders Insomnia 2.6
Social circumstances Mental disability 2.6
Nervous system disorders Paraesthesia 2.6
Gastrointestinal disorders Paraesthesia oral 2.6
Gastrointestinal disorders Pharyngitis 2.6
Skin and subcutaneous tissue disorders Rash 2.6
Nervous system disorders Somnolence 2.6
Nervous system disorders Thinking abnormal 2.6
Gastrointestinal disorders Throat irritation 2.6
Surgical and medical procedures Vasodilation procedure 2.6
Gastrointestinal disorders Vomiting
Psychiatric disorders Depression 2.5
Gastrointestinal disorders Diarrhoea 2.5
Investigations Body temperature increased
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.4
Musculoskeletal and connective tissue disorders Myalgia 2.4
Nervous system disorders Somnolence 2.4
Investigations Weight decreased 2.4
Investigations Body temperature increased
Gastrointestinal disorders Dysgeusia
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.2
Musculoskeletal and connective tissue disorders Myalgia 2.2
General disorders and administration site conditions Pain 2.2
Social circumstances Fasting 2.1
General disorders and administration site conditions Decreased appetite
Nervous system disorders Insomnia 2.0
Nervous system disorders Paraesthesia 2.0
Nervous system disorders Somnolence 2.0
Nervous system disorders Insomnia
General disorders and administration site conditions Pain
Psychiatric disorders Anxiety 1.7
Musculoskeletal and connective tissue disorders Arthralgia 1.7
Investigations Body temperature increased 1.7
General disorders and administration site conditions Decreased appetite 1.7
Psychiatric disorders Depression 1.7
General disorders and administration site conditions Discomfort 1.7
Cardiac disorders Dizziness 1.7
Gastrointestinal disorders Dysgeusia
Gastrointestinal disorders Dyspepsia 1.7
General disorders and administration site conditions Feeling abnormal 1.7
Gastrointestinal disorders Flatulence 1.7
General disorders and administration site conditions Hyperhidrosis 1.7
General disorders and administration site conditions Ill-defined disorder 1.7
Nervous system disorders Loss of consciousness 1.7
General disorders and administration site conditions Malaise 1.7
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.7
Musculoskeletal and connective tissue disorders Myalgia 1.7
General disorders and administration site conditions Pain 1.7
Vascular disorders Shock 1.7
Cardiac disorders Syncope 1.7
Gastrointestinal disorders Throat irritation 1.7
Surgical and medical procedures Vasodilation procedure 1.7
Investigations Weight decreased
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Dyspepsia
Social circumstances Fasting 1.5
Skin and subcutaneous tissue disorders Rash
Social circumstances Fasting 1.4
Social circumstances Fasting 1.3
Cardiac disorders Dizziness
General disorders and administration site conditions Hyperhidrosis
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Nervous system disorders Paraesthesia
Psychiatric disorders Anxiety
Psychiatric disorders Anxiety 0.9
Investigations Body temperature increased 0.9
Nervous system disorders Confusional state 0.9
General disorders and administration site conditions Decreased appetite 0.9
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 0.9
Cardiac disorders Dizziness 0.9
General disorders and administration site conditions Feeling abnormal 0.9
Gastrointestinal disorders Flatulence 0.9
Nervous system disorders Loss of consciousness 0.9
Social circumstances Mental disability 0.9
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
General disorders and administration site conditions Pain 0.9
Gastrointestinal disorders Pharyngitis 0.9
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 0.9
Vascular disorders Shock 0.9
Cardiac disorders Syncope 0.9
Nervous system disorders Thinking abnormal 0.9
Gastrointestinal disorders Throat irritation 0.9
Psychiatric disorders Anxiety 0.8
Gastrointestinal disorders Constipation 0.8
Skin and subcutaneous tissue disorders Dermatitis 0.8
Cardiac disorders Dizziness 0.8
Gastrointestinal disorders Flatulence 0.8
Nervous system disorders Insomnia 0.8
Nervous system disorders Loss of consciousness 0.8
Social circumstances Mental disability 0.8
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 0.8
Musculoskeletal and connective tissue disorders Myalgia 0.8
General disorders and administration site conditions Pain 0.8
Nervous system disorders Paraesthesia 0.8
Skin and subcutaneous tissue disorders Rash 0.8
Vascular disorders Shock 0.8
Cardiac disorders Syncope 0.8
Nervous system disorders Thinking abnormal 0.8
Gastrointestinal disorders Throat irritation 0.8
Surgical and medical procedures Vasodilation procedure 0.8
Musculoskeletal and connective tissue disorders Arthralgia
Psychiatric disorders Depression
General disorders and administration site conditions Discomfort 0.7
Gastrointestinal disorders Dyspepsia
General disorders and administration site conditions Feeling abnormal 0.7
Gastrointestinal disorders Flatulence
General disorders and administration site conditions Ill-defined disorder 0.7
General disorders and administration site conditions Malaise 0.7
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Nervous system disorders Paraesthesia
Nervous system disorders Confusional state
Nervous system disorders Confusional state 0.6
Cardiac disorders Dizziness 0.6
General disorders and administration site conditions Feeling abnormal
General disorders and administration site conditions Feeling abnormal 0.6
Nervous system disorders Loss of consciousness 0.6
Vascular disorders Shock 0.6
Cardiac disorders Syncope 0.6
Gastrointestinal disorders Constipation
Social circumstances Fasting
Social circumstances Mental disability
Nervous system disorders Paraesthesia
Gastrointestinal disorders Paraesthesia oral
Gastrointestinal disorders Pharyngitis
Gastrointestinal disorders Pharyngitis 0.4
Nervous system disorders Thinking abnormal
Gastrointestinal disorders Throat irritation
Social circumstances Fasting
Gastrointestinal disorders Constipation 0.2
General disorders and administration site conditions Discomfort
General disorders and administration site conditions Feeling abnormal
General disorders and administration site conditions Ill-defined disorder
General disorders and administration site conditions Malaise
Renal and urinary disorders Nocturia 0.2
Nervous system disorders Paraesthesia
Gastrointestinal disorders Paraesthesia oral
Nervous system disorders Somnolence
Gastrointestinal disorders Throat irritation

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Pregnancy, puerperium and perinatal conditions
11.88
Injury, poisoning and procedural complications
9.46
General disorders and administration site conditions
9.41
Nervous system disorders
5.91
Infections and infestations
5.58
Gastrointestinal disorders
5.04
Congenital, familial and genetic disorders
4.91
Vascular disorders
4.41
Metabolism and nutrition disorders
4.17
Investigations
4.13
Musculoskeletal and connective tissue disorders
3.97
Skin and subcutaneous tissue disorders
3.76
Psychiatric disorders
3.35
Renal and urinary disorders
3.31
Cardiac disorders
3.23
Respiratory, thoracic and mediastinal disorders
3.23
Hepatobiliary disorders
2.83
Blood and lymphatic system disorders
2.46

Cross References

Resources Reference
CAS NUMBER 155213-67-5
ChEBI 45409
ChEMBL CHEMBL163
DrugBank DB00503
DrugCentral 2391
EPA CompTox DTXSID1048627
FDA SRS O3J8G9O825
Human Metabolome Database HMDB0014646
Guide to Pharmacology 8804
KEGG C07240
PDB RIT
PharmGKB PA451260
PubChem 392622
SureChEMBL SCHEMBL6679
ZINC ZINC000003944422
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