TMC-647055

TMC-647055 is an experimental antiviral drug which was developed as a treatment for hepatitis C, and is in clinical trials as a combination treatment with ribavirin and simeprevir. It acts as a NS5b polymerase inhibitor.[1][2][3]

TMC-647055
Legal status
Legal status
  • US: Investigational drug
Identifiers
IUPAC name
  • 28-cyclohexyl-22-methoxy-10,16-dimethyl-9,9-dioxo-13-oxa-9λ6-thia-1,8,10,16-tetrazapentacyclo[16.8.1.12,6.13,26.020,25]nonacosa-2,4,6(29),18,20(25),21,23,26(28)-octaene-7,17-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC32H38N4O6S
Molar mass606.7 g·mol−1
3D model (JSmol)
SMILES
  • CN1CCOCCN(S(=O)(=O)NC(=O)C2=CC3=C(C=C2)C(=C4N3CC(=CC5=C4C=CC(=C5)OC)C1=O)C6CCCCC6)C
InChI
  • InChI=1S/C32H38N4O6S/c1-34-13-15-42-16-14-35(2)43(39,40)33-31(37)22-9-11-27-28(19-22)36-20-24(32(34)38)17-23-18-25(41-3)10-12-26(23)30(36)29(27)21-7-5-4-6-8-21/h9-12,17-19,21H,4-8,13-16,20H2,1-3H3,(H,33,37)
  • Key:UOBYJVFBFSLCTQ-UHFFFAOYSA-N

References
  1. Vendeville S, Lin TI, Hu L, Tahri A, McGowan D, Cummings MD, et al. (July 2012). "Finger loop inhibitors of the HCV NS5b polymerase. Part II. Optimization of tetracyclic indole-based macrocycle leading to the discovery of TMC647055". Bioorganic & Medicinal Chemistry Letters. 22 (13): 4437–43. doi:10.1016/j.bmcl.2012.04.113. PMID 22633687.
  2. Cummings MD, Lin TI, Hu L, Tahri A, McGowan D, Amssoms K, et al. (March 2014). "Discovery and early development of TMC647055, a non-nucleoside inhibitor of the hepatitis C virus NS5B polymerase". Journal of Medicinal Chemistry. 57 (5): 1880–92. doi:10.1021/jm401396p. PMID 24144360.
  3. Bourgeois S, Van Vlierberghe H, Moreno C, Orlent H, Nevens F, Arastéh K, et al. (February 2017). "Efficacy, safety and pharmacokinetics of simeprevir and TMC647055/ritonavir with or without ribavirin and JNJ-56914845 in HCV genotype 1 infection". BMC Gastroenterology. 17 (1): 26. doi:10.1186/s12876-017-0580-2. PMC 5303260. PMID 28187751.
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