Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Duvoglustat
- DrugBank Accession Number
- DB03206
- Background
An alpha-glucosidase inhibitor with antiviral action. Derivatives of deoxynojirimycin may have anti-HIV activity.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Duvoglustat (DB03206)
- Weight
- Average: 163.1717
Monoisotopic: 163.084457909 - Chemical Formula
- C6H13NO4
- Synonyms
- (+)-1-Deoxynojirimycin
- 1 deoxynojirimycin
- 1-deoxy-nojirimycin
- 1-deoxynojirimycin
- 1,5-deoxy-1,5-imino-D-mannitol
- 1,5-dideoxy-1,5-imino-D-glucitol
- 5-amino-1,5-dideoxy-D-glucopyranose
- D-1-deoxynojirimycin
- Deoxynojirimycin
- DNJ
- Duvoglustat
- External IDs
- BAY-H-5595
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism AMaltase-glucoamylase inhibitorHumans ALysosomal alpha-glucosidase inhibitorHumans ANeutral alpha-glucosidase AB inhibitorHumans ANeutral alpha-glucosidase C inhibitorHumans UCyclomaltodextrin glucanotransferase Not Available Bacillus sp. (strain 1011) UBeta-glucosidase A Not Available Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099) UEndoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase Not Available Humans UMannosyl-oligosaccharide alpha-1,2-mannosidase Not Available Penicillium citrinum UXylose isomerase Not Available Arthrobacter sp. (strain NRRL B3728) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
ORL-RAT LD50: > 5g/kg.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Duvoglustat hydrochloride 0RN23C42QR 73285-50-4 Not applicable
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Piperidines
- Sub Class
- Not Available
- Direct Parent
- Piperidines
- Alternative Parents
- Secondary alcohols / 1,2-aminoalcohols / Polyols / Dialkylamines / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- 1,2-aminoalcohol / Alcohol / Aliphatic heteromonocyclic compound / Amine / Azacycle / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound / Organooxygen compound
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- 2-(hydroxymethyl)piperidine-3,4,5-triol (CHEBI:44369)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- FZ56898FLE
- CAS number
- 19130-96-2
- InChI Key
- LXBIFEVIBLOUGU-JGWLITMVSA-N
- InChI
- InChI=1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/t3-,4+,5-,6-/m1/s1
- IUPAC Name
- (2R,3R,4R,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol
- SMILES
- OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O
References
- Synthesis Reference
Theo Schroder, Mathias Stubbe, "Process for preparing 1-deoxynojirimycin and N-derivatives thereof." U.S. Patent US4806650, issued September, 1986.
US4806650- General References
- Not Available
- External Links
- KEGG Drug
- D09605
- KEGG Compound
- C16843
- PubChem Compound
- 29435
- PubChem Substance
- 46507744
- ChemSpider
- 27360
- BindingDB
- 18351
- ChEBI
- 44369
- ChEMBL
- CHEMBL307429
- ZINC
- ZINC000003794714
- PDBe Ligand
- NOJ
- Wikipedia
- 1-Deoxynojirimycin
- PDB Entries
- 1die / 1dog / 1i75 / 1oim / 2j77 / 2jke / 2pwd / 2x2j / 2xg9 / 2ya2 … show 20 more
- MSDS
- Download (84.8 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2 Completed Treatment Glycogen Storage Disease Type II 1 somestatus stop reason just information to hide 2 Terminated Treatment Glycogen Storage Disease Type II 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -1.80 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 511.0 mg/mL ALOGPS logP -2.2 ALOGPS logP -2.9 Chemaxon logS 0.5 ALOGPS pKa (Strongest Acidic) 12.91 Chemaxon pKa (Strongest Basic) 8.06 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 92.95 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 36.57 m3·mol-1 Chemaxon Polarizability 15.85 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6137 Blood Brain Barrier - 0.8982 Caco-2 permeable - 0.8093 P-glycoprotein substrate Substrate 0.5892 P-glycoprotein inhibitor I Non-inhibitor 0.9255 P-glycoprotein inhibitor II Non-inhibitor 0.9514 Renal organic cation transporter Non-inhibitor 0.8207 CYP450 2C9 substrate Non-substrate 0.8718 CYP450 2D6 substrate Non-substrate 0.8056 CYP450 3A4 substrate Non-substrate 0.7092 CYP450 1A2 substrate Non-inhibitor 0.9401 CYP450 2C9 inhibitor Non-inhibitor 0.9543 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9671 CYP450 3A4 inhibitor Non-inhibitor 0.9886 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9896 Ames test Non AMES toxic 0.8765 Carcinogenicity Non-carcinogens 0.9653 Biodegradation Not ready biodegradable 0.7247 Rat acute toxicity 1.5447 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8879 hERG inhibition (predictor II) Non-inhibitor 0.9253
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0feb-7900000000-536465f5fd772045b134 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-002b-0900000000-179be3503509a3b85d39 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-01q9-1900000000-158c07bd46d97cf5da76 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004j-1900000000-54d3fe7d55f96a10c7ae Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03e9-3900000000-209067245351329bb22d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0pbc-9400000000-030cbb5d966f8ee8d6ca Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9100000000-de6e9c082c4064e26585 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 135.3836022 predictedDarkChem Lite v0.1.0 [M-H]- 135.3364022 predictedDarkChem Lite v0.1.0 [M-H]- 132.75908 predictedDeepCCS 1.0 (2019) [M+H]+ 135.5417022 predictedDarkChem Lite v0.1.0 [M+H]+ 136.1665022 predictedDarkChem Lite v0.1.0 [M+H]+ 135.15465 predictedDeepCCS 1.0 (2019) [M+Na]+ 135.3184022 predictedDarkChem Lite v0.1.0 [M+Na]+ 135.8327022 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.20528 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Alpha-(1,4) exo-glucosidase involved in breakdown of dietary starch oligosaccharides in small intestine. Cleaves the non-reducing alpha-(1,4)-linked glucose residue in linear dextrins with retention of anomeric center stereochemistry (PubMed:12547908, PubMed:18036614, PubMed:18356321, PubMed:22058037, PubMed:27480812). Mainly hydrolyzes short length oligomaltoses having two to seven glucose residues (PubMed:12547908, PubMed:18036614, PubMed:18356321, PubMed:22058037, PubMed:27480812). Can cleave alpha-(1,2), alpha-(1,3) and alpha-(1,6) glycosidic linkages with lower efficiency, whereas beta glycosidic linkages are usually not hydrolyzed (PubMed:27480812)
- Specific Function
- alpha-1,4-glucosidase activity
- Gene Name
- MGAM
- Uniprot ID
- O43451
- Uniprot Name
- Maltase-glucoamylase
- Molecular Weight
- 312020.05 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Essential for the degradation of glycogen in lysosomes (PubMed:14695532, PubMed:18429042, PubMed:1856189, PubMed:7717400). Has highest activity on alpha-1,4-linked glycosidic linkages, but can also hydrolyze alpha-1,6-linked glucans (PubMed:29061980)
- Specific Function
- alpha-1,4-glucosidase activity
- Gene Name
- GAA
- Uniprot ID
- P10253
- Uniprot Name
- Lysosomal alpha-glucosidase
- Molecular Weight
- 105322.935 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalytic subunit of glucosidase II that cleaves sequentially the 2 innermost alpha-1,3-linked glucose residues from the Glc(2)Man(9)GlcNAc(2) oligosaccharide precursor of immature glycoproteins (PubMed:10929008). Required for PKD1/Polycystin-1 and PKD2/Polycystin-2 maturation and localization to the cell surface and cilia (PubMed:27259053)
- Specific Function
- alpha-glucosidase activity
- Gene Name
- GANAB
- Uniprot ID
- Q14697
- Uniprot Name
- Neutral alpha-glucosidase AB
- Molecular Weight
- 106873.125 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Has alpha-glucosidase activity
- Specific Function
- alpha-1,4-glucosidase activity
- Gene Name
- GANC
- Uniprot ID
- Q8TET4
- Uniprot Name
- Neutral alpha-glucosidase C
- Molecular Weight
- 104333.445 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Bacillus sp. (strain 1011)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- alpha-amylase activity
- Gene Name
- cgt
- Uniprot ID
- P05618
- Uniprot Name
- Cyclomaltodextrin glucanotransferase
- Molecular Weight
- 78340.03 Da
References
- Kind
- Protein
- Organism
- Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- beta-glucosidase activity
- Gene Name
- bglA
- Uniprot ID
- Q08638
- Uniprot Name
- Beta-glucosidase A
- Molecular Weight
- 51548.055 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Involved in glycoprotein quality control targeting of misfolded glycoproteins for degradation. It primarily trims a single alpha-1,2-linked mannose residue from Man(9)GlcNAc(2) to produce Man(8)GlcNAc(2), but at high enzyme concentrations, as found in the ER quality control compartment (ERQC), it further trims the carbohydrates to Man(5-6)GlcNAc(2)
- Specific Function
- calcium ion binding
- Gene Name
- MAN1B1
- Uniprot ID
- Q9UKM7
- Uniprot Name
- Endoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase
- Molecular Weight
- 79579.18 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Penicillium citrinum
- Pharmacological action
- Unknown
- General Function
- Involved in the maturation of Asn-linked oligosaccharides. Progressively trim alpha-1,2-linked mannose residues from Man(9)GlcNAc(2) to produce Man(5)GlcNAc(2).
- Specific Function
- calcium ion binding
- Gene Name
- MSDC
- Uniprot ID
- P31723
- Uniprot Name
- Mannosyl-oligosaccharide alpha-1,2-mannosidase
- Molecular Weight
- 56569.37 Da
- Kind
- Protein
- Organism
- Arthrobacter sp. (strain NRRL B3728)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- magnesium ion binding
- Gene Name
- xylA
- Uniprot ID
- P12070
- Uniprot Name
- Xylose isomerase
- Molecular Weight
- 43291.15 Da
References
- Collyer CA, Blow DM: Observations of reaction intermediates and the mechanism of aldose-ketose interconversion by D-xylose isomerase. Proc Natl Acad Sci U S A. 1990 Feb;87(4):1362-6. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:23