Bersacapavir is an experimental drug for the treatment of hepatitis B.[1] It prevents hepatitis B virus (HBV) from replicating by inhibiting the formation of its capsid.[2] It is also being studied for use in combination with JNJ-73763989, a small interfering RNA that targets HBV RNAs.[3]

Bersacapavir
Legal status
Legal status
  • Investigational
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC16H14F4N4O3S
Molar mass418.37 g·mol−1
3D model (JSmol)
  • C[C@@H](C(F)(F)F)NS(=O)(=O)C1=CN(C(=C1)C(=O)NC2=CC(=C(C=C2)F)C#N)C
  • InChI=1S/C16H14F4N4O3S/c1-9(16(18,19)20)23-28(26,27)12-6-14(24(2)8-12)15(25)22-11-3-4-13(17)10(5-11)7-21/h3-6,8-9,23H,1-2H3,(H,22,25)/t9-/m0/s1
  • Key:SBVBIDUKSBJYEF-VIFPVBQESA-N

It can be synthesized beginning with N-methylpyrrole.[4][5]

References

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  1. ^ "Bersacapavir". AdisInsight. Springer Nature Switzerland AG.
  2. ^ Bassit L, Amblard F, Patel D, Biteau N, Chen Z, Kasthuri M, et al. (2023). "The premise of capsid assembly modulators towards eliminating HBV persistence". Expert Opinion on Drug Discovery. 18 (9): 1031–1041. doi:10.1080/17460441.2023.2239701. PMC 10530454. PMID 37477111.
  3. ^ Agarwal K, Buti M, van Bömmel F, Lampertico P, Janczewska E, Bourliere M, et al. (September 2024). "JNJ-73763989 and bersacapavir treatment in nucleos(t)ide analogue-suppressed patients with chronic hepatitis B: REEF-2". Journal of Hepatology. 81 (3): 404–414. doi:10.1016/j.jhep.2024.03.046. PMID 38583491.
  4. ^ Medina F, Maton WM, Bongartz JP, Kossler D, Eriksson M, Weerts J, et al. (2024). "Process Development of Bersacapavir, Part 2. Early Game Route Selection: Catalytic versus Stoichiometric Haloform-Type Amidation". Organic Process Research & Development. doi:10.1021/acs.oprd.4c00154.
  5. ^ Medina F, Maton WM, Weerts J, Eriksson M, Bongartz JP, Clemens K, et al. (2024). "Process Development of Bersacapavir, Part 1: Route Scouting Effort toward a Key Amide Intermediate". Organic Process Research & Development. doi:10.1021/acs.oprd.4c00153.