Celgosivir

Names

[ Name ]:
Celgosivir

[Synonym ]:
6-O-butanoylcastanospermine
UNII:895VG117HN
BuCast
(1S,6S,7S,8R,8aR)-1,7,8-Trihydroxyoctahydro-6-indolizinyl butyrate
MX-3253
B-T
6-O-Butyryltanosopermine
6-O-Butanoyltanospermine
Butanoic Acid (1S,6S,7S,8R,8aR)-Octahydro-1,7,8-trihydroxy-6-indolizinyl Ester
[(1S,6S,7S,8R,8aR)-1,7,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl] butanoate
MDL 28,574
UNII-895VG117HN
6-O-butyryltanospermine
(1S,6S,7S,8R,8aR)-1,7,8-Trihydroxyoctahydroindolizin-6-yl butyrate
Butanoic acid, (1S,6S,7S,8R,8aR)-octahydro-1,7,8-trihydroxy-6-indolizinyl ester
Celgosivir

Biological Activity

[Description]:

Celgosivir (MBI 3253; MDL 28574; MX3253) is a novel α-glucosidase I inhibitor, an enzyme that plays a critical role in viral maturation by initiating the processing of the N-linked oligosaccharides of viral envelope glycoproteins.[1]

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HCV

Natural Products >> Alkaloid

Research Areas >> Infection

[Target]

IC50: 16 and 47 umol/L (alpha-glucosidase I, Using plaque assay and a cytopathic assay)[2]

[In Vitro]

The quantity of THP-1 cells is 1 × 105 , cells were washed once with media and replaced with 500 μl with a serial 4-fold dilution starting from 200 μM or 50 μM.[3]

[In Vivo]

Celgosivir, stored at 100 mg/ml in PBS at 30 °C, were diluted with PBS before each dosing to obtain 1 mg/200 μl (50 mg/kg) or 0.2 mg/200 μl (10 mg/kg). [3]

[References]

[1]. Durantel D. Celgosivir, an alpha-glucosidase I inhibitor for the potential treatment of HCV infection. Curr Opin Investig Drugs. 2009 Aug, 10(8):860-70.

[2]. Whitby K et al. Action of celgosivir (6 O-butanoyl castanospermine) against the pestivirus BVDV: implications for thetreatment of hepatitis C. Antivir Chem Chemother, 2004 May, 15(3):141-51.

[3]. Satoru Watanabe，Kitti Wing-Ki Chan et al. Optimizing celgosivir therapy in mouse models of dengue virus infection of serotypes 1 and 2: The search for a window for potential therapeutic efficacy. Antiviral Research, March 2016, Pages 10-19.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
422.9±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₂H₂₁NO₅

[ Molecular Weight ]:
259.299

[ Flash Point ]:
209.6±28.7 °C

[ Exact Mass ]:
259.141968

[ PSA ]:
90.23000

[ LogP ]:
-0.82

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.569

[ Storage condition ]:
2-8℃

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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