Celgosivir

Celgosivir
Clinical data
Other names	6-O-Butanoylcastanospermine; MDL-28574; MX-3253
Legal status
Legal status	Investigational;
Identifiers
	IUPAC name [(1S,6S,7S,8R,8aR)-1,7,8-Trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl] butanoate;
CAS Number	121104-96-9;
PubChem CID	60734; 3033824;
ChemSpider	54737;
UNII	895VG117HN;
CompTox Dashboard (EPA)	DTXSID70153153 ;
Chemical and physical data
Formula	C12H21NO5
Molar mass	259.302 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCC(=O)O[C@H]1CN2CC[C@@H]([C@@H]2[C@H]([C@@H]1O)O)O;
	InChI InChI=1S/C12H21NO5/c1-2-3-9(15)18-8-6-13-5-4-7(14)10(13)12(17)11(8)16/h7-8,10-12,14,16-17H,2-6H2,1H3/t7-,8-,10+,11+,12+/m0/s1; Key:HTJGLYIJVSDQAE-VWNXEWBOSA-N;

Celgosivir, in development by Migenix for the treatment of hepatitis C virus (HCV) infection, is an oral prodrug of the natural product castanospermine that inhibits alpha-glucosidase I, an enzyme that plays a critical role in viral maturation by initiating the processing of the N-linked oligosaccharides of viral envelope glycoproteins. Celgosivir is well absorbed in vitro and in vivo, and is rapidly converted to castanospermine. Celgosivir has a novel mechanism of action (preventing the glycosylation of viral proteins by the host), and demonstrates broad antiviral activity in vitro.