TMC-647055

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	1204416-97-6;
PubChem CID	44556044;
DrugBank	DB11822;
ChemSpider	28522119;
UNII	11BD024G7J;
ChEMBL	ChEMBL2043025;
CompTox Dashboard (EPA)	DTXSID90152860 ;
Chemical and physical data
Formula	C32H38N4O6S
Molar mass	606.7 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

References

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.
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.
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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