SOFOSBUVIR

Search structure
Trade Names:
Synonyms:
Status: Approved (2013)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J05AP08
UNII: WJ6CA3ZU8B

Structure
InChI Key TTZHDVOVKQGIBA-IQWMDFIBSA-N
Smile CC(C)OC(=O)[C@H](C)N[P@](=O)(OC[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@](C)(F)[C@@H]1O)Oc1ccccc1
InChI
InChI=1S/C22H29FN3O9P/c1-13(2)33-19(29)14(3)25-36(31,35-15-8-6-5-7-9-15)32-12-16-18(28)22(4,23)20(34-16)26-11-10-17(27)24-21(26)30/h5-11,13-14,16,18,20,28H,12H2,1-4H3,(H,25,31)(H,24,27,30)/t14-,16+,18+,20+,22+,36-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H29FN3O9P
Molecular Weight 529.46
AlogP 1.66
Hydrogen Bond Acceptor 10.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 10.0
Polar Surface Area 158.18
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 36.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Hepatitis C virus NS5B RNA-dependent RNA polymerase inhibitor FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 60000 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 8400 - - -
Enzyme Protease Serine protease Serine protease PA clan Serine protease S29 family Serine protease S29 regulatory subfamily
- - - - 61
Enzyme Protease Serine protease Serine protease PA clan Serine protease S29 family
- - - - 61
Enzyme Transferase
34-589 - - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hepatitis C, Chronic 4 D019698 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Infections 3 D007239 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Hepatitis B, Chronic 2 D019694 ClinicalTrials

Related Entries

Scaffolds

Mixture
Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Asthenia 59.0
General disorders and administration site conditions Fatigue 59.0
General disorders and administration site conditions Asthenia 55.0
General disorders and administration site conditions Fatigue 55.0
Nervous system disorders Headache 44.0
General disorders and administration site conditions Asthenia 38.0
General disorders and administration site conditions Fatigue 38.0
Nervous system disorders Headache 36.0
Gastrointestinal disorders Nausea 34.0
General disorders and administration site conditions Asthenia 30.0
General disorders and administration site conditions Fatigue 30.0
Nervous system disorders Headache 30.0
Nervous system disorders Insomnia 29.0
Gastrointestinal disorders Nausea 29.0
Skin and subcutaneous tissue disorders Pruritus 27.0
Nervous system disorders Insomnia 25.0
General disorders and administration site conditions Asthenia 24.0
General disorders and administration site conditions Fatigue 24.0
Nervous system disorders Headache 24.0
Gastrointestinal disorders Nausea 22.0
Blood and lymphatic system disorders Anaemia 21.0
General disorders and administration site conditions Asthenia 21.0
Nervous system disorders Headache 20.0
Investigations Body temperature increased 18.0
General disorders and administration site conditions Chills 18.0
General disorders and administration site conditions Decreased appetite 18.0
Skin and subcutaneous tissue disorders Dermatitis 18.0
General disorders and administration site conditions Influenza like illness 18.0
Gastrointestinal disorders Nausea 18.0
Skin and subcutaneous tissue disorders Rash 18.0
General disorders and administration site conditions Chills 17.0
Gastrointestinal disorders Diarrhoea 17.0
Blood and lymphatic system disorders Neutropenia 17.0
Skin and subcutaneous tissue disorders Pruritus 17.0
General disorders and administration site conditions Influenza like illness 16.0
Nervous system disorders Insomnia 16.0
General disorders and administration site conditions Irritability 16.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 16.0
Musculoskeletal and connective tissue disorders Myalgia 16.0
Nervous system disorders Insomnia 15.0
Investigations Body temperature increased 14.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 14.0
Musculoskeletal and connective tissue disorders Myalgia 14.0
General disorders and administration site conditions Irritability 13.0
Gastrointestinal disorders Nausea 13.0
Blood and lymphatic system disorders Anaemia 12.0
Gastrointestinal disorders Diarrhoea 12.0
Blood and lymphatic system disorders Neutropenia 12.0
Skin and subcutaneous tissue disorders Pruritus 11.0
Blood and lymphatic system disorders Anaemia 10.0
General disorders and administration site conditions Decreased appetite 10.0
General disorders and administration site conditions Irritability 10.0
Skin and subcutaneous tissue disorders Dermatitis 9.0
Gastrointestinal disorders Diarrhoea 9.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 9.0
Musculoskeletal and connective tissue disorders Myalgia 9.0
Skin and subcutaneous tissue disorders Rash 9.0
Skin and subcutaneous tissue disorders Dermatitis 8.0
Skin and subcutaneous tissue disorders Pruritus 8.0
Skin and subcutaneous tissue disorders Rash 8.0
Blood and lymphatic system disorders Anaemia 6.0
General disorders and administration site conditions Asthenia 6.0
General disorders and administration site conditions Decreased appetite 6.0
Gastrointestinal disorders Diarrhoea 6.0
General disorders and administration site conditions Influenza like illness 6.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 6.0
Musculoskeletal and connective tissue disorders Myalgia 6.0
General disorders and administration site conditions Asthenia 5.0
Investigations Body temperature increased 4.0
Nervous system disorders Insomnia 4.0
General disorders and administration site conditions Asthenia 3.0
General disorders and administration site conditions Influenza like illness 3.0
General disorders and administration site conditions Chills 2.0
General disorders and administration site conditions Chills 1.0
General disorders and administration site conditions Irritability 1.0
Blood and lymphatic system disorders Neutropenia 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
14.07
Nervous system disorders
9.2
Hepatobiliary disorders
8.42
Gastrointestinal disorders
7.74
Psychiatric disorders
6.96
Injury, poisoning and procedural complications
5.41
Vascular disorders
5.36
Investigations
5.35
Cardiac disorders
5.29
Infections and infestations
4.92
Skin and subcutaneous tissue disorders
4.6
Respiratory, thoracic and mediastinal disorders
4.26
Blood and lymphatic system disorders
3.23
Musculoskeletal and connective tissue disorders
2.76
Metabolism and nutrition disorders
2.54
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.43
Renal and urinary disorders
2.38

Cross References

Resources Reference
CAS NUMBER 1190307-88-0
ChEBI 85083
ChEMBL CHEMBL1259059
DrugBank DB08934
DrugCentral 4811
FDA SRS WJ6CA3ZU8B
Guide to Pharmacology 7368
PharmGKB PA166122593
PubChem 45375808
SureChEMBL SCHEMBL2010114
ZINC ZINC000100074252
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