| Chemical Information | |
| Antiviral agent ID | DrugRepV_0052 | |
| Antiviral agent name | Sofosbuvir |  |
| 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 |  |
| SMILES (canonical) | CC(C)OC(=O)C(C)NP(=O)(OCC1C(C(C(O1)N2C=CC(=O)NC2=O)(C)F)O)OC3=CC=CC=C3 | |
| SMILES (isomeric) | C[C@@H](C(=O)OC(C)C)NP(=O)(OC[C@@H]1[C@H]([C@@]([C@@H](O1)N2C=CC(=O)NC2=O)(C)F)O)OC3=CC=CC=C3 | |
| Molecular Formula | C22H29FN3O9P | |
| Molecular Weight (g/mol) | 529.46 | |
| InChl | 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 | |
| Common Name | Sofosbuvir | |
| Synonyms | Sovaldi| Resof | Hepcvir | SoviHep | |
| Structural Information | |
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| Clinical Information | |
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Category | Antiinfectives For Systemic Use
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Primary Indication (Clinical trial phases) | Approved
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| Biological Information | |
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Primary Indication (Disease Category) | Infectious Disease
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Primary Indication (Disease) | Hepatitis C virus | Acquired immunodeficiency syndrome
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Secondary Indication | Zika virus (ZIKV) NA H/PF/2013 |   |
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Secondary Indication (Approaches) | Experimental | |
| Secondary Indication (Methods) | In-vitro | |
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Secondary Indication (Potential drug target) | Nucleotide analouge
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Secondary Indication (Model system) [cell lines/ animal models] | Vero
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Secondary Indication (Mode of viral infection) | Adsorption
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Secondary Indication (Viral titer) | 0.1 MOI
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Secondary Indication (Mode of drug delivery) | Culture
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Secondary Indication (Time of drug delivery) | After adsorption
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Secondary Indication (Duration of drug delivery) | 5 days
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Secondary Indication (Drug concentration) | >50 μM
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Secondary Indication (Cell based assay) | Cytopathic effect (CPE) assay
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Secondary Indication (Change) | No significant effect
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Secondary Indication (Type of Inhibition) | IC50 [ 0 % ] | |
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Secondary Indication (Cytotoxicity) | >100 μM | |
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Reference | Mumtaz N, Jimmerson LC, Bushman LR, Kiser JJ, Aron G, Reusken CBEM, Koopmans MPG, van Kampen JJA..Cell-line dependent antiviral activity of sofosbuvir against Zika virus..Antiviral Res. 2017 Oct;146:161-163. doi: 10.1016/j.antiviral.2017.09.004. Epub 2017 Sep 11. PMID:28912011
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Comment | Sofosbuvir is a phosphoramidate nucleotide analogue and the metabolic pathway involves hydrolysis of the carboxyl ester moiety by cathepsin A (CatA) or carboxylesterase 1 (CES1) and phosphor-amidate cleavage by histidine triad nucleotide-binding protein 1 (HINT1) followed by phosphorylation by uridine monophosphate- cytidine monophosphate kinase (UMP-CMP kinase) and nucleoside diphosphate kinase (NDPK) to its active metabolite 007-TP, a uridine-triphosphate analogue which inhibits the viral RNA dependent RNA polymerase (RdRp). Lower intracellular concentration of the active triphosphate metabolite of sofosbuvir
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