An inhibitor of UDP-glucose ceramide glucosyltransferase and β-glucosidase 2
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Labeled Version(s)
34852N-Butyldeoxynojirimycin-d9 (hydrochloride)
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N-Butyldeoxynojirimycin (hydrochloride)

Item No. 21065

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-butyl-2R-(hydroxymethyl)-3R,4R,5S-piperidinetriol, monohydrochloride
CAS Number
210110-90-0
Synonyms
  • Miglustat
  • NB-DNJ
Molecular Formula
C10H21NO4 • HCl
Formula Weight
255.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
OC[C@H]1N(CCCC)C[C@H](O)[C@@H](O)[C@@H]1O.Cl
InChi Code
InChI=1S/C10H21NO4.ClH/c1-2-3-4-11-5-8(13)10(15)9(14)7(11)6-12;/h7-10,12-15H,2-6H2,1H3;1H/t7-,8+,9-,10-;/m1./s1
InChi Key
QPAFAUYWVZMWPR-ZSOUGHPYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

    $108

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    10 mg

    $178

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    25 mg

    $389

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    Product Description

    NB-DNJ is an iminosugar that inhibits UDP-glucose ceramide glucosyltransferase and β-glucosidase 2 (IC50s = 32 and 81 μM, respectively, for the rat recombinant enzymes).1 It also increases the activity of wild-type acid β-glucosidase, as well as the S364R, N370S, V15M, or M123T mutants, in COS-7 cells expressing the human enzymes when used at a concentration of 10 µM.2 NB-DNJ also inhibits HIV-1 and HIV-2 infection of peripheral blood mononuclear cells (PBMCs; IC50s = 282 and 211 μM, respectively).3 Formulations containing NB-DNJ have been used in the treatment of Gaucher disease, an inborn error of metabolism characterized as a lysosomal storage disorder resulting from substantial deficiency of β-glucosidase.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lee, J.C., Francis, S., Dutta, D., et al. Synthesis and evaluation of eight- and four-membered iminosugar analogues as inhibitors of testicular ceramide-specific glucosyltransferase, testicular β-glucosidase 2, and other glycosidases. The Journal of Organic Chemistry 77(7), 3082-3098 (2012).

    2. Alfonso, P., Pampín, S., Estrada, J., et al. Miglustat (NB-DNJ) works as a chaperone for mutated acid β-glucosidase in cells transfected with several Gaucher disease mutations. Blood Cells Mol. Dis. 35(2), 268-276 (2005).

    3. Pollock, S., Dwek, R.A., Burton, D.R., et al. N-Butyldeoxynojirimycin is a broadly effective anti-HIV therapy significantly enhanced by targeted liposome delivery. AIDS 22(15), 1961-1969 (2008).

    Product Citations

    Watanabe, S., Oyama, M., Iwai, T., et al. Glucosylceramide synthase inhibitor ameliorates chronic inflammatory pain. J. Pharmacol. Sci. 156(4), 235-238 (2024).