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B8299

Sigma-Aldrich

N-Butyldeoxynojirimycin

film (dried in situ), ≥98% (TLC)

Synonym(s):

Miglustat, NB-DNJ

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About This Item

Empirical Formula (Hill Notation):
C10H21NO4
CAS Number:
72599-27-0
Molecular Weight:
219.28
MDL number:
MFCD00272581
UNSPSC Code:
12352200
PubChem Substance ID:
24892070
NACRES:
NA.32

product name

N-Butyldeoxynojirimycin, film (dried in situ)

assay

≥98% (TLC)

Quality Level

200

form

film (dried in situ)

solubility

water: 9.80-10.20 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

CCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO

InChI

1S/C10H21NO4/c1-2-3-4-11-5-8(13)10(15)9(14)7(11)6-12/h7-10,12-15H,2-6H2,1H3/t7-,8+,9-,10-/m1/s1

InChI key

UQRORFVVSGFNRO-UTINFBMNSA-N

Gene Information

human ... UGCG(7357)

Related Categories

General description

N-Butyldeoxynojirimycin is an alkylated product of imino sugar deoxynojirimycin.

Application

N-Butyldeoxynojirimycin has been used:
  • in the inhibition of glycolipid synthesis in neuroblastoma cells
  • in the inhibition the ceramide-specific glycosyltransferase in hepatocytes
  • in the inhibition of β-glucosidase (GBA2) using fluorescence- activity assay in human embryonic kidney (HEK293) cells.

Biochem/physiol Actions

N-Butyldeoxynojirimycin is an inhibitor of glucosyltransferase and α-glucosidases. N-Butyldeoxynojirimycin, also known as misglustat, reduces glycolipid levels by substrate reduction therapy (SRT) and is effectively used for the treatment of glycosphingolipid lysosomal storage disorder, Gaucher disease.
α-glucosidase Inhibitor

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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How adhesion/growth-regulatory galectins-1 and-3 attain cell specificity: case study defining their target on neuroblastoma cells (SK-N-MC) and marked affinity regulation by affecting microdomain organization of the membrane
Kopitz J, et al.
IUBMB Life, 62(8), 624-628 (2010)
Imiglucerase in the treatment of Gaucher disease: a history and perspective
Deegan PB and Cox TM
Drug design, development and therapy, 6, 81-81 (2012)
Andrés Felipe Leal et al.
International journal of molecular sciences, 21(17) (2020-09-02)
GM2 gangliosidoses are a group of pathologies characterized by GM2 ganglioside accumulation into the lysosome due to mutations on the genes encoding for the β-hexosaminidases subunits or the GM2 activator protein. Three GM2 gangliosidoses have been described: Tay-Sachs disease, Sandhoff
Beom Hee Lee et al.
Medicine, 96(45), e8492-e8492 (2017-11-16)
Gaucher disease (GD) is caused by a deficiency in the lysosomal enzyme glucocerebrosidase. Enzyme replacement therapy (ERT) is recommended for clinical improvement. The efficacy and safety of a new imiglucerase, Abcertin, were assessed in 7 Egyptian patients with treatment-naïve type
The role of the iminosugar N-butyldeoxynojirimycin (miglustat) in the management of type I (non-neuronopathic) Gaucher disease: a position statement
Cox TM, et al.
Journal of inherited metabolic disease, 26(6), 513-526 (2003)
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