sofosbuvir   Click here for help

GtoPdb Ligand ID: 7368

Synonyms: GI-7977 | PSI 7977 | Sovaldi®
Approved drug PDB Ligand
sofosbuvir is an approved drug (FDA (2013), EMA (2014))
Compound class: Synthetic organic
Comment: Sofosbuvir is a nucleotide analogue whose action inhibits hepatitis C virus (HCV) NS5B RNA-dependent RNA polymerase. It acts as a chain terminator to limit viral RNA replication.
Sofosbuvir is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 167.99
Molecular weight 529.16
XLogP 1.93
No. Lipinski's rules broken 1
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Canonical SMILES CC(OC(=O)C(NP(=O)(Oc1ccccc1)OCC1OC(C(C1O)(C)F)n1ccc(=O)[nH]c1=O)C)C
Isomeric SMILES CC(OC(=O)[C@@H](N[P@@](=O)(Oc1ccccc1)OC[C@H]1O[C@H]([C@]([C@@H]1O)(C)F)n1ccc(=O)[nH]c1=O)C)C
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2013), EMA (2014))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
propan-2-yl (2S)-2-[[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
International Nonproprietary Names Click here for help
INN number INN
9665 sofosbuvir
Synonyms Click here for help
GI-7977 | PSI 7977 | Sovaldi®
Database Links Click here for help
CAS Registry No. 1190307-88-0 (source: Scifinder)
ChEMBL Ligand CHEMBL1259059
DrugBank Ligand DB08934
DrugCentral Ligand 4811
GtoPdb PubChem SID 178103940
PubChem CID 45375808
Search Google for chemical match using the InChIKey TTZHDVOVKQGIBA-IQWMDFIBSA-N
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UniChem Compound Search for chemical match using the InChIKey TTZHDVOVKQGIBA-IQWMDFIBSA-N
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Wikipedia Sofosbuvir