Sofosbuvir

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Cat Number

API1190307880

CAS Number

1190307-88-0

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CAS Number

1190307-88-0

EINECS

695-717-4

Storage

Store at room temperature

Synonyms

PSI-7977; SOVALDI; GS 7977; WJ6CA3ZU8B; CHEBI:85083; DTXSID701027632; EPCLUSA COMPONENT SOFOSBUVIR

Molecular Formula

C22H29FN3O9P

Molecular Weight

529.5

Smiles

C[C@@H](C(=O)OC(C)C)N[P@](=O)(OC[C@@H]1[C@H]([C@@]([C@@H](O1)N2C=CC(=O)NC2=O)(C)F)O)OC3=CC=CC=C3

Appearance

White solid

Melting Point

120-125°C

Relative Density

1.4

General Description

Sofosbuvir is a nucleotide analog with a uridine base and a phosphoramidate prodrug moiety, specifically a 2'‑deoxy‑2'‑α‑fluoro‑β‑C‑methyluridine derivative. Its structure is a white to off‑white crystalline powder with a molecular weight of 529.45 Da. The prodrug design enhances oral bioavailability and hepatic delivery.

Mechanism of Action

Sofosbuvir is a prodrug that is metabolized intracellularly to the active triphosphate (GS‑461203), which acts as a potent inhibitor of the NS5B polymerase of hepatitis C virus. The active metabolite acts as a chain terminator, incorporating into the growing viral RNA and causing premature termination of RNA synthesis. This prevents replication of the viral genome.

Application

Sofosbuvir is indicated for the treatment of chronic hepatitis C (HCV) infection in adults, in combination with other direct‑acting antiviral agents (ledipasvir, velpatasvir, or ribavirin). It is effective against all major genotypes (1‑6) and is a cornerstone of HCV therapy. The drug has a high barrier to resistance and a favorable safety profile.

Meta-analysis of 5 RCTs (2,315 patients) on sofosbuvir/velpatasvir/voxilaprevir for chronic HCV found a grade 3 hyperglycemia incidence of 1.5% (RR 0.015, 95% CI 0.010–0.020, P<0.001). Subgroup analysis showed higher IRR for genotype 3 vs genotype 1 (4.13, 95% CI 1.52–11.22).

Fig. 1 Flowchart of the identification of eligible trials. (Hung HY, et al., 2023)

References

Hung HY, et al. The impact of sofosbuvir/velpatasvir/voxilaprevir treatment on serum hyperglycemia in hepatitis C virus infections: a systematic review and meta-analysis. Ann Med. 2023;55(1):463-479.

In 15 patients with hepatitis C and porphyria cutanea tarda (PCT), ledipasvir/sofosbuvir cured HCV in 12 of 13 patients (92%). All 12 cured of HCV achieved sustained clinical remission of PCT without phlebotomy or hydroxychloroquine. Direct‑acting antivirals treat both HCV and PCT, eliminating the need for additional therapies.

Fig. 2 Time Course of Serum ALT (U/L) during and after Treatment with Ledipasvir/Sofosbuvir. (Bonkovsky HL, et al., 2023)

References

Bonkovsky HL, et al. Ledipasvir/Sofosbuvir Is Effective as Sole Treatment of Porphyria Cutanea Tarda with Chronic Hepatitis C. Dig Dis Sci. 2023;68(6):2738-2746.

Does Sofosbuvir require protection from moisture during long-term storage?

Yes, it is hygroscopic and susceptible to hydrolysis of the phosphate ester and uridine moiety. Store in tightly sealed, moisture-proof containers with desiccant.

What is the recommended storage temperature for Sofosbuvir?

Store at controlled room temperature (15-25°C). Avoid temperatures above 30°C, which accelerate degradation and formation of the diastereomeric impurity.

Is Sofosbuvir stable in tablet formulations with standard excipients?

Yes, when formulated with moisture-protective packaging (e.g., HDPE bottles with desiccant).

How is the impurity sofosbuvir diastereomer (a process-related impurity) monitored?

This impurity is quantified using a stability-indicating chiral HPLC method, ensuring it remains within ICH limits.