DrugRepV|Encyclopedia for antivirals

Chemical, Structural, Clinical and Biological details of Antiviral agents ID: DrugRepV_2119

Chemical Information
Antiviral agent ID DrugRepV_2119
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) 529.458

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

Clinical Information
Category Antiinfectives For Systemic Use
Primary Indication (Clinical trial phases) Approved
Biological Information
Primary Indication (Disease Category) Infectious Disease
Primary Indication (Disease) Hepatitis C virus | Acquired immunodeficiency syndrome
Secondary Indication Zika virus (ZIKV) NA PRVABC-59
Secondary Indication (Approaches) Experimental
Secondary Indication (Methods) in-vitro
Secondary Indication (Model system) [cell lines/ animal models] Huh-7
Secondary Indication (Mode of viral infection) Adsorption
Secondary Indication (Viral titer) 0.1 MOI
Secondary Indication (Mode of drug delivery) Culture
Secondary Indication (Time of drug delivery) During inoculation
Secondary Indication (Duration of drug delivery) 72 hours
Secondary Indication (Drug concentration) 32 μM
Secondary Indication (Cell based assay) Real-time PCR
Secondary Indication (Change) Decrease
Secondary Indication (Type of Inhibition) Viral titre [ >1 Log10 (GE/ml) ]
Secondary Indication (Cytotoxicity) >200 μM
Reference Bullard-Feibelman KM, Govero J, Zhu Z, Salazar V, Veselinovic M, Diamond MS, Geiss BJ..The FDA-approved drug sofosbuvir inhibits Zika virus infection..Antiviral Res. 2017 Jan;137:134-140. doi: 10.1016/j.antiviral.2016.11.023. Epub 2016 Nov 27. PMID:27902933
Comment Cell culture studies established that sofosbuvir efficiently inhibits replication and infection of several ZIKV strains in multiple human tumor cell lines and isolated human fetal-derived neuronal stem cells. Moreover, oral treatment with sofosbuvir protected against ZIKV-induced death in mice. These results suggest that sofosbuvir may be a candidate for further evaluation as a therapy against ZIKV infection in humans.

Copyright © 2019. CSIR-Institute of Microbial Technology, Chandigarh, INDIA.

Chemical Information
Antiviral agent ID	DrugRepV_2119
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)	529.458
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

Clinical Information
Category	Antiinfectives For Systemic Use
Primary Indication (Clinical trial phases)	Approved
Biological Information
Primary Indication (Disease Category)	Infectious Disease
Primary Indication (Disease)	Hepatitis C virus \| Acquired immunodeficiency syndrome
Secondary Indication	Zika virus (ZIKV) NA PRVABC-59
Secondary Indication (Approaches)	Experimental
Secondary Indication (Methods)	in-vitro
Secondary Indication (Model system) [cell lines/ animal models]	Huh-7
Secondary Indication (Mode of viral infection)	Adsorption
Secondary Indication (Viral titer)	0.1 MOI
Secondary Indication (Mode of drug delivery)	Culture
Secondary Indication (Time of drug delivery)	During inoculation
Secondary Indication (Duration of drug delivery)	72 hours
Secondary Indication (Drug concentration)	32 μM
Secondary Indication (Cell based assay)	Real-time PCR
Secondary Indication (Change)	Decrease
Secondary Indication (Type of Inhibition)	Viral titre [ >1 Log10 (GE/ml) ]
Secondary Indication (Cytotoxicity)	>200 μM
Reference	Bullard-Feibelman KM, Govero J, Zhu Z, Salazar V, Veselinovic M, Diamond MS, Geiss BJ..The FDA-approved drug sofosbuvir inhibits Zika virus infection..Antiviral Res. 2017 Jan;137:134-140. doi: 10.1016/j.antiviral.2016.11.023. Epub 2016 Nov 27. PMID:27902933
Comment	Cell culture studies established that sofosbuvir efficiently inhibits replication and infection of several ZIKV strains in multiple human tumor cell lines and isolated human fetal-derived neuronal stem cells. Moreover, oral treatment with sofosbuvir protected against ZIKV-induced death in mice. These results suggest that sofosbuvir may be a candidate for further evaluation as a therapy against ZIKV infection in humans.