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	606.74 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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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[16.8.1.1^2,6.1^3,26.0^20,25]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	606.74 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