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Compound Detail

CHEMBL1029

MIGLUSTAT
💊 Approved Drug
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💊 Approved Drug
CCCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO

Basic Information

ChEMBL ID CHEMBL1029
Name MIGLUSTAT
Phase Approved
Structure Type MOL
InChI Key UQRORFVVSGFNRO-UTINFBMNSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL4297283

Known Names

Butyldeoxynojirimycin Miglustat Miglustat dipharma Miglustat gen.orph N-butyldeoxynojirimycin OGT 918 OGT-918 Opfolda Yargesa Zavesca
20
Targets
71
Activities
3
Assay Types
0
PK Parameters
20
Publications
10
Known Names
13
Indications
1
Mechanisms

Molecular Properties

219.3
MW (Da)
-1.45
ALogP
5
HBA
4
HBD
84.2
PSA (Ų)
0.46
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2002
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product First in Class Prodrug
USAN Stem -stat
USAN Year 2003

Extended Properties

Molecular Formula C10H21NO4
MW 219.28
Aromatic Rings 0
Heavy Atoms 15
NP-Likeness 1.24

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Ceramide glucosyltransferase inhibitor INHIBITOR Ceramide glucosyltransferase

Indications

Gaucher Disease Gaucher Disease Glycogen Storage Disease Type II Niemann-Pick Diseases Gangliosidoses, GM2 Glycogen Storage Disease Niemann-Pick Disease, Type C Sandhoff Disease Cystic Fibrosis HIV Infections Spastic Paraplegia, Hereditary Diarrhea Neuronal Ceroid-Lipofuscinoses

ATC Classification

A16AX06
miglustat
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: OTHER ALIMENTARY TRACT AND METABOLISM PRODUCTS

Activity Summary

IC50 64 meas. best 7.85
EC50 4 meas. best 4.93
Ki 3 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-glucosidase
CHEMBL3761
IC50 7.85 6.7957 14.0 7
Lysosomal alpha-glucosidase
CHEMBL2608
IC50 7.0 7.0 100.0 2
Non-lysosomal glucosylceramidase
CHEMBL5614
IC50 6.85 6.85 140.0 1
Lysosomal alpha-glucosidase
CHEMBL2608
Ki 6.7 6.7 200.0 1
Alpha-glucosidase
CHEMBL5280
IC50 6.38 6.38 420.0 1
Sucrase-isomaltase, intestinal
CHEMBL2748
IC50 6.3 6.3 500.0 1
Sucrase-isomaltase, intestinal
CHEMBL3114
IC50 6.24 5.3014 580.0 7
Sucrase-isomaltase
CHEMBL1667666
IC50 6.22 6.02 600.0 2
Unchecked
CHEMBL612545
IC50 6.0 5.14 1000.0 6
CuFi-1
CHEMBL4513124
IC50 5.7 5.7 2000.0 1
Maltase-glucoamylase
CHEMBL2074
IC50 5.68 5.365 2100.0 2
Acidic alpha-glucosidase
CHEMBL3513
IC50 5.68 5.48 2100.0 2
Unchecked
CHEMBL612545
Ki 5.43 5.43 3700.0 1
Lysosomal alpha-glucosidase
CHEMBL1667668
IC50 5.05 5.05 9000.0 1
Glycogen debranching enzyme
CHEMBL5272
IC50 5.0 5.0 10000.0 1
Lysosomal alpha-glucosidase
CHEMBL1667668
EC50 4.93 4.93 11800.0 1
Trehalase
CHEMBL3248
IC50 4.89 4.655 13000.0 2
Ceramide glucosyltransferase
CHEMBL2063
IC50 4.7 4.584 20000.0 5
Ceramide glucosyltransferase
CHEMBL6013
IC50 4.64 4.425 22900.0 4
Uncharacterized protein
CHEMBL2176863
IC50 4.44 4.44 36000.0 1
SARS-CoV-2
CHEMBL4303835
IC50 4.38 4.38 42200.0 1
Unchecked
CHEMBL612545
EC50 4.25 4.25 56400.0 1
Bovine viral diarrhea virus 1
CHEMBL612571
EC50 4.0 4.0 100000.0 1
Dengue virus
CHEMBL613757
EC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-glucosidase IC50 = 14.0 nM 7.85 Inhibition of NLGase in human SH-SY5Y cells using MUG-Gluc as fluorogenic substr... 31075609
Lysosomal alpha-glucosidase IC50 = 100.0 nM 7.0 Inhibition of human lysosomal alpha glucosidase 19853441
Lysosomal alpha-glucosidase IC50 = 100.0 nM 7.0 Inhibition of lysosomal alpha-glucosidase by HPLC 20000679
Non-lysosomal glucosylceramidase IC50 = 140.0 nM 6.85 Inhibition of conduritol beta-epoxide-sensitive mouse glucosylceramidase 17848577
Lysosomal alpha-glucosidase Ki = 200.0 nM 6.7 Inhibition of human GAA using 4-methylumbelliferyl-alpha-D-glucopyranoside as su... 35072486
Beta-glucosidase IC50 = 230.0 nM 6.64 Inhibition of human GBA2 19853441
Beta-glucosidase IC50 = 230.0 nM 6.64 Inhibition of GBA2 (unknown origin) 25250725
Beta-glucosidase IC50 = 230.0 nM 6.64 Inhibition of GBA2 by HPLC 20000679
Beta-glucosidase IC50 = 230.0 nM 6.64 Inhibition of recombinant GBA2 preincubated with compound for 30 mins using 4-me... 24900289
Beta-glucosidase IC50 = 230.0 nM 6.64 Inhibition of glucosylceramidase 2 from spleen of patient with gaucher's disease... 24900342
Beta-glucosidase IC50 = 300.0 nM 6.52 Inhibition of non-lysosomal glucosylceramidase 21354674
Alpha-glucosidase IC50 = 420.0 nM 6.38 Inhibitory activity against alpha-Glucosidase from rice 15546715
Sucrase-isomaltase, intestinal IC50 = 500.0 nM 6.3 Inhibition of sucrase by HPLC 20000679
Sucrase-isomaltase, intestinal IC50 = 580.0 nM 6.24 Inhibition of Sucrase in rat intestinal brush border membranes by D-glucose oxid... 7608901
Sucrase-isomaltase IC50 = 600.0 nM 6.22 Inhibition of sucrase in mouse intestinal input by glucose release assay 24900289
Unchecked IC50 = 1000.0 nM 6.0 Inhibition of rice alpha glucosidase 19853441
Sucrase-isomaltase IC50 = 1500.0 nM 5.82 Inhibition of wild type C57BL/6 mouse small intestinal sucrase/isomaltase using ... 29112434
CuFi-1 IC50 = 2000.0 nM 5.7 Anti-inflammatory activity in human CuFi1 cells assessed as reduction in Pseudom... 31075609
Sucrase-isomaltase, intestinal IC50 = 2100.0 nM 5.68 Inhibition of rat intestinal maltase using disaccharide 15546715
Maltase-glucoamylase IC50 = 2100.0 nM 5.68 Inhibition of Glycosidases (maltase) in rat intestinal brush border membranes by... 7608901

Literature References

PubMed DOI Target Context # Activities
17848577 10.1074/jbc.m702387200 Mus musculus 32
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
29112434 10.1021/acs.jmedchem.7b00646 Unchecked 13
20000679 10.1021/jm901281m Mus musculus 6
19853441 10.1016/j.bmcl.2009.10.022 Unchecked 5
16019946 10.1080/00498250400028197 ADMET 4
7608901 10.1021/jm00013a012 Unchecked 4
17848577 10.1074/jbc.m702387200 Non-lysosomal glucosylceramidase 4
31075609 10.1016/j.ejmech.2019.04.061 CuFi-1 4
20014752 10.1021/tx900326k Hepatotoxicity 3
15546715 10.1016/j.bmcl.2004.09.086 Sucrase-isomaltase, intestinal 3
37468498 10.1038/s41467-023-40064-9 Androgen receptor 2
29112434 10.1021/acs.jmedchem.7b00646 Sucrase-isomaltase 2
23363020 10.1021/jm301557k Lysosomal alpha-glucosidase 2
7608901 10.1021/jm00013a012 MOLT-4 2
7608901 10.1021/jm00013a012 MT4 2
21292481 10.1016/j.bmcl.2010.12.106 Unchecked 2
23106358 10.1021/jm301304e Sucrase-isomaltase, intestinal 2
7608901 10.1021/jm00013a012 Alpha-mannosidase 2 2
23363020 10.1021/jm301557k Unchecked 2

Data from ChEMBL 36 via Core Engine