North-methanocarbathymidine

North-methanocarbathymidine
Clinical data
Trade names	N-MCT
Legal status
Legal status	US: Investigational drug;
Identifiers
	IUPAC name 1-[(1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-bicyclo[3.1.0]hexanyl]-5-methylpyrimidine-2,4-dione;
CAS Number	156126-12-4 ;
PubChem CID	445212;
UNII	LTM5S02010;
Chemical and physical data
Formula	C12H16N2O4
Molar mass	252.270 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@]3([C@@H]2C3)CO)O;
	InChI InChI=1S/C12H16N2O4/c1-6-4-14(11(18)13-10(6)17)8-2-9(16)12(5-15)3-7(8)12/h4,7-9,15-16H,2-3,5H2,1H3,(H,13,17,18)/t7-,8+,9+,12+/m1/s1; Key:NOWRLNPOENZFHP-ARHDFHRDSA-N;

North-Methanocarbathymidine (N-MCT) is an antiviral drug which is an analogue of thymidine, and shows activity against herpesviruses, orthopoxviruses and HIV,^[1]^[2]^[3]^[4] though it has not been introduced into clinical use.

References

^ Zhu W, Burnette A, Dorjsuren D, Roberts PE, Huleihel M, Shoemaker RH, et al. (December 2005). "Potent antiviral activity of north-methanocarbathymidine against Kaposi's sarcoma-associated herpesvirus". Antimicrobial Agents and Chemotherapy. 49 (12): 4965–73. doi:10.1128/AAC.49.12.4965-4973.2005. PMC 1315933. PMID 16304159.
^ Marquez VE, Hughes SH, Sei S, Agbaria R (September 2006). "The history of N-methanocarbathymidine: the investigation of a conformational concept leads to the discovery of a potent and selective nucleoside antiviral agent". Antiviral Research. 71 (2–3): 268–75. doi:10.1016/j.antiviral.2006.04.012. PMID 16730077.
^ Prichard MN, Kern ER (September 2010). "Antiviral Activity of 4'-thioIDU and Thymidine Analogs against Orthopoxviruses". Viruses. 2 (9): 1968–83. doi:10.3390/v2091968. PMC 3185742. PMID 21994716.
^ De Clercq E (November 2013). "Highlights in antiviral drug research: antivirals at the horizon". Medicinal Research Reviews. 33 (6): 1215–48. doi:10.1002/med.21256. PMC 7168470. PMID 22553111.