sofosbuvir   

GtoPdb Ligand ID: 7368

Synonyms: GI-7977 | PSI 7977 | Sovaldi®
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) RNA polymerase.
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).
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key TTZHDVOVKQGIBA-IQWMDFIBSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2013), EMA (2014))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
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
INN number INN
9665 sofosbuvir
Synonyms
GI-7977 | PSI 7977 | Sovaldi®
Database Links
CAS Registry No. 1190307-88-0 (source: Scifinder)
ChEMBL Ligand CHEMBL1259059
DrugBank Ligand DB08934
DrugCentral Ligand 4811
GtoPdb PubChem SID 178103940
PubChem CID 45375808
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Search UniChem for chemical match using the InChIKey TTZHDVOVKQGIBA-IQWMDFIBSA-N
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Wikipedia Sofosbuvir