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Velpatasvir structure
Velpatasvir structure


Iupac Name:methyl N-[(1R)-2-[(2S,4S)-2-[5-[6-[(2S,5S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-21-oxa-5,7-diazapentacyclo[,11.04,8.014,19]henicosa-1(13),2,4(8),5,9,11,14(19),15,17-nonaen-17-yl]-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate
CAS No.: 1377049-84-7
Molecular Weight:883.00200
Modify Date.: 2022-11-26 11:45

ChEBI: A complex organic heteropentacyclic compound that is a hepatitis C virus nonstructural protein 5A inhibitor used in combination with sofosbuvir (under the brand name Epclusa) for treatment of patients with chronic hepatitis C of all six major genotypes.

Velpatasvir is a complex organic heteropentacyclic compound that is a hepatitis C virus nonstructural protein 5A inhibitor used in combination with sofosbuvir (under the brand name Epclusa) for treatment of patients with chronic hepatitis C of all six major genotypes. It has a role as an antiviral drug and a hepatitis C virus nonstructural protein 5A inhibitor. It is an organic heteropentacyclic compound, a N-acylpyrrolidine, a L-valine derivative, a carbamate ester, a member of imidazoles, a ring assembly and an ether.|Velpatasvir is a Direct-Acting Antiviral (DAA) medication used as part of combination therapy to treat chronic Hepatitis C, an infectious liver disease caused by infection with Hepatitis C Virus (HCV). HCV is a single-stranded RNA virus that is categorized into nine distinct genotypes, with genotype 1 being the most common in the United States, and affecting 72% of all chronic HCV patients. Velpatasvir acts as a defective substrate for NS5A (Non-Structural Protein 5A), a non-enzymatic viral protein that plays a key role in Hepatitis C Virus replication, assembly, and modulation of host immune responses. Treatment options for chronic Hepatitis C have advanced significantly since 2011, with the development of Direct Acting Antivirals (DAAs) such as velpatasvir. Notably, velpatasvir has a significantly higher barrier to resistance than the first generation NS5A inhibitors, such as [DB09027] and [DB09102], making it a highly potent and reliable alternative for treatment of chronic Hepatitis C. In a joint recommendation published in 2016, the American Association for the Study of Liver Diseases (AASLD) and the Infectious Diseases Society of America (IDSA) recommend Velpatasvir as first line therapy in combination with sofosbuvir for all six genotypes of Hepatitis C. Velpatasvir is currently only available within a fixed dose combination product as Epclusa with [DB08934], another direct acting antiviral. Goals of therapy for Epclusa include the intent to cure, or achieve a sustained virologic response (SVR), after 12 weeks of daily therapy. SVR and eradication of HCV infection is associated with significant long-term health benefits including reduced liver-related damage, improved quality of life, reduced incidence of Hepatocellular Carcinoma, and reduced all-cause mortality and risk of requiring a liver transplant. Since June 2016, Velpatasvir has been available as a fixed dose combination product with [DB08934], as the commercially available product Epclusa. Epclusa is the first combination HCV product indicated for the treatment of all genotypes of Hepatitis C with or without cirrhosis. It is also currently the most potent HCV antiviral medication on the market with a sustained virologic response (SVR) after 12 weeks of therapy of 93-99% depending on genotype and level of cirrhosis and a high barrier to resistance. Both Canadian and American guidelines list Epclusa as a first line recommendation for all genotypes of HCV.|Velpatasvir is a Hepatitis C Virus NS5A Inhibitor. The mechanism of action of velpatasvir is as a Breast Cancer Resistance Protein Inhibitor, and P-Glycoprotein Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor, and Organic Anion Transporting Polypeptide 2B1 Inhibitor.|Velpatasvir is an orally available inhibitor of the hepatitis C virus (HCV) non-structural protein 5A (NS5A) replication complex, with potential activity against HCV genotypes 1-6. Although the exact mechanism of action of velpatasvir has not yet been completely determined, upon oral administration and intracellular uptake, it appears to bind to domain I of the NS5A protein. This inhibits the activity of the NS5A protein and results in the disruption of the viral RNA replication complex, blockage of viral HCV RNA production, and inhibition of viral replication. NS5A, a zinc-binding and proline-rich hydrophilic phosphoprotein, plays a crucial role in HCV RNA replication. HCV is a small, enveloped, single-stranded RNA virus belonging to the Flaviviridae family.

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1. Names and Identifiers
1.1 Name
1.2 Synonyms

Carbamic acid, N-[(1R)-2-[(2S,4S)-2-[4-[1,11-dihydro-2-[(2S,5S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-5-methyl-2-pyrrolidinyl][2]benzopyrano[4',3':6,7]naphth[1,2-d]imidazol-9-yl]-1H-imidazol-2-yl]-4-(methoxymethyl)-1-pyrrolidinyl]-2-oxo-1-phenylethyl]-, methyl ester CS-2204 GS 5816 GS-5816 methyl ((2s)-1-((2s,5s)-2-(9-(2-((2s,4s)-1-((2r)-2-((methoxycarbonyl)amino)-2-phenylacetyl)-4-(methoxymethyl)pyrrolidin-2-yl)-1h-imidazol-5-yl)-1,11-dihydroisochromeno(4',3':6,7)naphtho(1,2-d)imidazol-2-yl)-5-methylpyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamate Methyl [(2S)-1-[(2S,5S)-2-[9-[2-[(2S,4S)-1-[(2R)-2-[(methoxycarbonyl)amino]-2-phenylacetyl]-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl]-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl]-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate Methyl {(2S)-1-[(2S,5S)-2-(9-{2-[(2S,4S)-1-{(2R)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4-(methoxymethyl)-2-pyrrolidinyl]-1H-imidazol-4-yl}-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-5-methyl-1-pyrrolidinyl]-3-methyl-1-oxo-2-butanyl}carbamate Unifiram (DM-232) Velpatasvir API velpatasvir(GS-5816)

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C49H54N8O8 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
3.1 Density
1.314±0.06 g/cm3(Predicted)
3.1 Refractive index
3.1 Precise Quality
3.1 PSA
3.1 logP
3.1 Solubility
Insuluble (1.7E-4 g/L) (25 oC),
3.2 pKa
3. Use and Manufacturing
4.1 Definition
ChEBI: A complex organic heteropentacyclic compound that is a hepatitis C virus nonstructural protein 5A inhibitor used in combination with sofosbuvir (under the brand name Epclusa) for treatment of patients with chronic hepatitis C of all six major genotypes. VelpatasvirSupplier

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s) no data available
Signal word

no data available

Hazard statement(s)

no data available

Precautionary statement(s)

no data available


no data available


no data available


no data available

2.3 Other hazards which do not result in classification

no data available

5. Other Information
5.0 Mesh
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)
5.1 Absorption
Oral bioavailability of 25-30%.|94% excreted in feces with 77% as parent compound. 0.4% excreted in urine.|1.4-1.6 L/kg.|Estimated 0.12 L/h/kg [A19175.
5.2 Metabolism
Some metabolism by CYP2B6, CYP2C8, and CYP3A4.
5.3 Biological Half Life
5.4 Use Classification
Human drugs -> Epclusa -> EMA Drug Category|Antivirals for systemic use -> Human pharmacotherapeutic group|Human drugs -> Vosevi -> EMA Drug Category|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
5.5 Definition
ChEBI: A complex organic heteropentacyclic compound that is a hepatitis C virus nonstructural protein 5A inhibitor used in combination with sofosbuvir (under the brand name Epclusa) for treatment of patients with chronic hepatitis C of all six major genotypes.
5.6 Target
5.7 Uses
Velpatasvir is a NS5A inhibitor in patients with hepatitis C (HCV) infection.
6. Computational chemical data
  • Molecular Weight: 883.00200g/mol
  • Molecular Formula: C49H54N8O8
  • Compound Is Canonicalized: True
  • XLogP3-AA: 6.2
  • Exact Mass: 882.40646071
  • Monoisotopic Mass: 882.40646071
  • Complexity: 1690
  • Rotatable Bond Count: 13
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 10
  • Topological Polar Surface Area: 193
  • Heavy Atom Count: 65
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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8. Realated Product Infomation