| Iupac Name: | [(1''S'',6''S'',7''S'',8''R'',8a''R'')-1,7,8-Trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl] butanoate |
| Legal Status: | Investigational |
| Cas Number: | 121104-96-9 |
| Unii: | 895VG117HN |
| Pubchem: | 60734 |
| Pubchem2: | 3033824 |
| Synonyms: | 6-O-Butanoylcastanospermine; MDL-28574; MX-3253 |
| Chemspiderid: | 54737 |
| C: | 12 |
| H: | 21 |
| N: | 1 |
| O: | 5 |
| Stdinchi: | 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 |
| Stdinchikey: | HTJGLYIJVSDQAE-VWNXEWBOSA-N |
| Smiles: | CCCC(=O)O[C@H]1CN2CC[C@@H]([C@@H]2[C@H]([C@@H]1O)O)O |
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.[1]
Celgosivir is not efficient as a monotherapy for the treatment of HCV, but has demonstrated a synergistic effect in combination with pegylated interferon alfa-2b plus ribavirin, both in vitro and in phase II clinical trials that last up to 1 year in patients with chronic HCV infection. Celgosivir may prove to be a valuable component for combination therapy and may help to prevent the apparition of drug resistance. Long-term toxicity studies are necessary to confirm the safety of celgosivir in humans.[1]
Although generally safe and well tolerated, celgosivir does not seem to reduce viral load or fever burden in patients with dengue fever.[2]