An inhibitor of glucosylceramide synthase, glucocerebrosidase, and β-glucosidase 2
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N-(n-Butyl)deoxygalactonojirimycin

Item No. 19520

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-butyl-2R-(hydroxymethyl)-3S,4R,5S-piperidinetriol
CAS Number
141206-42-0
Synonyms
  • Lucerastat
  • NBDGJ
Molecular Formula
C10H21NO4
Formula Weight
219.3
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mLDMSO: 30 mg/mLEthanol: 5 mg/mLPBS (pH 7.2): 10 mg/mL
SMILES
OC[C@H]1N(CCCC)C[C@H](O)[C@@H](O)[C@H]1O
InChi Code
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-XFWSIPNHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $49

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    1 mg

    $86

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    5 mg

    $213

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    Product Description

    N-(n-Butyl)deoxygalactonojirimycin (NB-DGJ) is an inhibitor of the glycolipid biosynthesis enzyme glucosylceramide synthase and the glycolipid catabolic enzymes glucocerebrosidase (GBA) and β-glucosidase 2 (GBA2).1,2,3,4,5 It also inhibits acid α-glucosidase, sucrase, maltase, and lactase.4 NB-DGJ (0.5-500 µM) reduces glycolipid levels in HL-60 and WEHI-3B cells.1 It decreases brain ganglioside levels in a Glb1-/- neonatal mouse model of GM1 gangliosidosis when administered intraperitoneally at doses of 600 and 1,200 mg/kg four times per day for three days.6 NB-DGJ (1-1,200 mg/kg per day for 35 days) increases testicular glucosylceramide levels in mice.2 NB-DGJ induces abnormal spermatid and acrosome formation, as well as reduces motility, in isolated mouse epididymal sperm when administered at doses of 15, 25, and 50 mg/kg per day.5 It also induces infertility, an effect that is reversed by withdrawal, in the same model.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Platt, F.M., Neises, G.R., Karlsson, G.B., et al. N-Butyldeoxygalactonojirimycin inhibits glycolipid biosynthesis but does not affect N-linked oligosaccharide processing. J. Biol. Chem 269(43), 27108-27114 (1994).

    2. Walden, C.M., Sandhoff, R., Chuang, C.C., et al. Accumulation of glucosylceramide in murine testis, caused by inhibition of β-glucosidase 2: implications for spermatogenesis. The Journal of Biological Chemisty 282(45), 32655-32664 (2007).

    3. Ridley, C.M., Thur, K.E., Shanahan, J., et al. β-Glucosidase 2 (GBA2) activity and imino sugar pharmacology. The Journal of Biological Chemisty 288(36), 26052-26066 (2013).

    4. Wennekes, T., Meijer, A.J., Groen, A.K., et al. Dual-action lipophilic iminosugar improves glycemic control in obese rodents by reduction of visceral glycosphingolipids and buffering of carbohydrate assimilation. J. Med. Chem. 53(2), 689-698 (2010).

    5. Gupta, V., Hild, S.A., Jakkaraj, S.R., et al. N-Butyldeoxygalactonojirimycin induces reversible infertility in male CD rats. Int. J. Mol. Sci. 21(1), (2020).

    6. Kasperzyk, J.L., El-Abbadi, M.M., Hauser, E.C., et al. N-butyldeoxygalactonojirimycin reduces neonatal brain ganglioside content in a mouse model of GM1 gangliosidosis. J. Neurochem. 89(3), 645-653 (2004).