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SML2314

Sigma-Aldrich

Celgosivir

≥98% (HPLC)

Synonym(s):

6-O-Butanoylcastanospermine, 6-O-Butyrylcastanospermine, BuCast, Butanoic acid (1S,6S,7S,8R,8aR)-octahydro-1,7,8-trihydroxy-6-indolizinyl ester, Butanoic acid [1S-(1α,6β,7α,8β,8aβ)]-octahydro-1,7,8-trihydroxy-6-indolizinyl ester, MDL 28,574, MDL 28574, MDL-28574

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About This Item

Empirical Formula (Hill Notation):
C12H21NO5
CAS Number:
121104-96-9
Molecular Weight:
259.30
MDL number:
MFCD00886617
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage condition

desiccated
under inert gas

color

white to beige

solubility

H2O: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O[C@@H]1[C@@H](OC(CCC)=O)CN2[C@@]([C@@H](O)CC2)([H])[C@H]1O

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

InChI key

HTJGLYIJVSDQAE-VWNXEWBOSA-N

Biochem/physiol Actions

Celgosivir is a prodrug of natural bicyclic iminosugar castanospermine that exhibits antiviral activity in vivo including HCV and dengue. Celgosivir is an inhibitor of α-glucosidases, which inhibits glycoprotein processing in cell culture. Apparently inhibition of α-glucosidases within infected cell prevents secretion of virus.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Andrew C Sayce et al.
PLoS neglected tropical diseases, 10(3), e0004524-e0004524 (2016-03-15)
It has long been thought that iminosugar antiviral activity is a function of inhibition of endoplasmic reticulum-resident α-glucosidases, and on this basis, many iminosugars have been investigated as therapeutic agents for treatment of infection by a diverse spectrum of viruses

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