Daclatasvir

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Daclatasvir
250px
Names
IUPAC name
Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
Other names
BMS-790052; NATDAC
Identifiers
1009119-64-5 YesY
ChEBI CHEBI:82977 YesY
ChEMBL ChEMBL2023898
ChEMBL2303621
ChemSpider 24609522
Jmol 3D model Interactive image
  • InChI=1S/C40H50N8O6/c1-23(2)33(45-39(51)53-5)37(49)47-19-7-9-31(47)35-41-21-29(43-35)27-15-11-25(12-16-27)26-13-17-28(18-14-26)30-22-42-36(44-30)32-10-8-20-48(32)38(50)34(24(3)4)46-40(52)54-6/h11-18,21-24,31-34H,7-10,19-20H2,1-6H3,(H,41,43)(H,42,44)(H,45,51)(H,46,52)/t31-,32-,33-,34-/m0/s1
    Key: FKRSSPOQAMALKA-CUPIEXAXSA-N
  • InChI=1/C40H50N8O6/c1-23(2)33(45-39(51)53-5)37(49)47-19-7-9-31(47)35-41-21-29(43-35)27-15-11-25(12-16-27)26-13-17-28(18-14-26)30-22-42-36(44-30)32-10-8-20-48(32)38(50)34(24(3)4)46-40(52)54-6/h11-18,21-24,31-34H,7-10,19-20H2,1-6H3,(H,41,43)(H,42,44)(H,45,51)(H,46,52)/t31-,32-,33-,34-/m0/s1
    Key: FKRSSPOQAMALKA-CUPIEXAXBX
  • CC(C)[C@@H](C(=O)N1CCC[C@H]1c2[nH]cc(n2)c3ccc(cc3)c4ccc(cc4)c5c[nH]c(n5)[C@@H]6CCCN6C(=O)[C@H](C(C)C)NC(=O)OC)NC(=O)OC
Properties
C40H50N8O6
Molar mass 738.89 g·mol−1
Vapor pressure {{{value}}}
Pharmacology
ATC code J05AX14
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Daclatasvir (USAN,[1] formerly BMS-790052, trade name Daklinza) is a drug for the treatment of hepatitis C (HCV). It was developed by Bristol-Myers Squibb and was approved in Europe on 22 August 2014. Daklinza gained its FDA approval on July 24, 2015 in the United States; it is approved for Hepatitis C genotype 3 infections.[2]

A generic version of daclatasvir is expected to be approved in India before the end of 2015.[citation needed]

Daclatasvir inhibits the HCV nonstructural protein NS5A.[3][4] Recent research suggests that it targets two steps of the viral replication process, enabling rapid decline of HCV RNA.[5]

Daclatasvir has been tested in combination regimens with pegylated interferon and ribavirin,[6] as well as with other direct-acting antiviral agents including asunaprevir[7][8][9][10] and sofosbuvir.[11][12]

It is on the World Health Organization's List of Essential Medicines, a list of the most important medications needed in a basic health system.[13]

There has been significant controversy over the price that Bristol-Myers Squibb has chosen to charge for the drug. As of December 2015 it cost between $50,000 – $84,000 in high-income countries.[14]

References

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  1. ↑ Statement on a Nonproprietary Name Adopted by the USAN Council
  2. ↑ http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm455888.htm
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Modeling shows that the NS5A inhibitor daclatasvir has two modes of action and yields a shorter estimate of the hepatitis C virus half-life. Guedj, J et al. Proceedings of the National Academy of Sciences. February 19, 2013.
  6. ↑ AASLD: Daclatasvir with Pegylated Interferon/Ribavirin Produces High Rates of HCV Suppression. Highleyman, L. HIVandHepatitis.com. 6 December 2011.
  7. ↑ Preliminary Study of Two Antiviral Agents for Hepatitis C Genotype 1. Lok, A et al. New England Journal of Medicine. 366(3):216-224. January 19, 2012.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ AASLD: Daclatasvir plus Asunaprevir Rapidly Suppresses HCV in Prior Null Responders. Highleyman, L. HIVandHepatitis.com. 8 November 2011.
  10. ↑ High rate of response to BMS HCV drugs in harder-to-treat patients – but interferon-free prospects differ by sub-genotype. Alcorn, K. Aidsmap.com. 12 November 2012.
  11. ↑ AASLD 2012: Sofosbuvir + Daclatasvir Dual Regimen Cures Most Patients with HCV Genotypes 1, 2, or 3. Highleyman, L. HIVandHepatitis.com. 15 November 2012.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ http://i-base.info/htb/29226
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