| Synonyms |
[(1S,6S,7S,8R,8aR)-1,7,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl] butanoate;hydrochloride; Celgosivir HCl; UNII-70U2NQU0FP; Celgosivir (hydrochloride); MDL 28574A |
| IUPAC Name |
[(1S,6S,7S,8R,8aR)-1,7,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl] butanoate;hydrochloride |
| Molecular Weight |
295.76 |
| Molecular Formula |
C12H22ClNO5 |
| Canonical SMILES |
CCCC(=O)OC1CN2CCC(C2C(C1O)O)O.Cl |
| InChI |
1S/C12H21NO5.ClH/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;1H/t7-,8-,10+,11+,12+;/m0./s1 |
| InChIKey |
KXNZMBFOWDNCRU-QVMZSJACSA-N |
| Boiling Point |
422.9°C at 760 mmHg |
| Flash Point |
209.6°C |
| Purity |
≥98% (HPLC) |
| Solubility |
H2O: ≥ 200 mg/mL |
| Appearance |
White to gray (Solid) |
| Storage |
Store in a cool and dry place (or refer to the Certificate of Analysis). |
| Animal Admin |
To mimic ADE, inject 20 μg/mouse intraperitoneal mouse monoclonal antibody against the DENV E protein one day before infection. For treatment during infection, intraperitoneal injections of sigosvir (50 mg / kg) twice a day starting on day 0, day 1 or day 2 for 5 days. The survival of mice is tracked until day 10 and survival curves are plotted. |
| Complexity |
311 |
| Exact Mass |
295.1186505 |
| In Vitro |
Celgosivir is more effective (IC50=20 μM) than the parent molecule (IC50=254 μM) at causing the accumulation of glucosylated oligosaccharides in HIV-infected cells by inhibition of glycoprotein processing. Celgosivir exhibits potent antiviral activity against HIV-1 with an IC50 of 2.0±2.3 μM. Celgosivir inhibits BVDV with IC50 values of 16 and 47 μM in plaque assay and cytopathic effect assay, respectively. Celgosivir inhibits DENV2 replication with an EC50 of 0.2 μM. The EC50 values against DENV1, 3 and 4 are less than 0.7 μM. |
| In Vivo |
Celgosivir fully protects AG129 mice from lethal infection with a mouse adapted dengue virus at a dose of 50 mg/kg and is effective even after 48 h delayed treatment. Pharmacokinetics studies of celgosivir in mice shows that it rapidly metabolizes to castanospermine. During primary infection with a mouse-adapted DENV strain S221, mice shows increased viremia on day 3, yet 80% survived day 10 with virus completely cleared by day 8. |
| PSA |
90.23000 |
| Target |
Glucosidase; HCV; HIV |
| Vapor Pressure |
6.34E-09mmHg at 25°C |
![{PARAM:[Name]}()](https://resource.bocsci.com/structure/141117-12-6.gif)
