N-BUTYLDEOXYNOJIRIMYCIN

Base Information

• Chemical Name: N-BUTYLDEOXYNOJIRIMYCIN
• CAS No.: 72599-27-0
• Deprecated CAS: 134282-77-2
• Molecular Formula: C10H21NO4
• Molecular Weight: 219.281
• Hs Code.: 2933399090
• European Community (EC) Number: 689-232-7
• UNII: ADN3S497AZ
• DSSTox Substance ID: DTXSID6045618
• Nikkaji Number: J258.518I
• Wikipedia: Miglustat
• Wikidata: Q425911
• NCI Thesaurus Code: C1222
• RXCUI: 402316
• Pharos Ligand ID: YYWFKNMQHWUS
• Metabolomics Workbench ID: 42779
• ChEMBL ID: CHEMBL1029
• Mol file: 72599-27-0.mol

Synonyms:3,4,5-Piperidinetriol,1-butyl-2-(hydroxymethyl)-, [2R-(2a,3b,4a,5b)]-;Miglustat;N-Butyl-1-deoxynojirimycin;N-Butyldeoxynojirimycin;N-Butylmoranoline;NB-DNJ;OGT 918;SC 48334;Zavesca;

Chemical Property of N-BUTYLDEOXYNOJIRIMYCIN

Chemical Property:

• Vapor Pressure: 7.27E-08mmHg at 25°C
• Melting Point: 126-127℃
• Boiling Point: 394.7±42.0 °C at 760 mmHg
• PKA: 13.72±0.70(Predicted)
• Flash Point: 215.4±26.5 °C
• PSA: 84.16000
• Density: 1.2±0.1 g/cm³
• LogP: -1.51640
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in water at 10mg/ml
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 219.14705815
• Heavy Atom Count: 15
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

N-Butyldeoxynojirimycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Gaucher Disease Agents
• Canonical SMILES: CCCCN1CC(C(C(C1CO)O)O)O
• Isomeric SMILES: CCCCN1C[C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O
• Recent ClinicalTrials: A Study to Evaluate the Safety, Efficacy, PK, PD and Immunogenicity of Cipaglucosidase Alfa/Miglustat in IOPD Subjects Aged 0 to <18
• Recent EU Clinical Trials: Phase 2 pharmacological experimental study to test the safety of miglustat in subjects with hereditary spastic paraplegia type 11
• Recent NIPH Clinical Trials: ATB200/AT2221phase3 double blind randomized study
• Description: Miglustat is an N-alkylated iminosugar, launched as an oral treatment for mild to moderate type 1 Gaucher’s disease in adult patients for whom enzyme replacement therapy is not a therapeutic option. It is readily synthesized from D-glucose in three steps by first converting to N-butylglucamine via reductive amination with butylamine, followed by a microbial oxidation to an aminofuranose intermediate and subsequent reductive cyclization. Type 1 Gaucher’s disease is a metabolic disorder caused by the lysosomal accumulation of certain glycosphingolipids (GSLs) as a result of deficiency in their degradation. Enlargement of the liver and spleen, low blood platelet and bone lesions are among the key symptoms of this disease. Miglustat acts by inhibiting glucosylceramide synthase, a glucosyl transferase enzyme in the biosynthesis of most GSLs, which results in the lowering of GSLs to a level that can be effectively cleared. Up to 50% reduction in liver and splenocyte GSL levels are achieved in mice by long-term administration of Miglustat (600– 1800 mg/kg/day for 118 days). Miglustat, dosed at 50 and 100 mg in Gaucher patients, exhibits dose proportionate pharmacokinetics (tmax=2.5 h, t1/2=6 to 7 h) and ＞90% oral bioavailability. Steady-state plasma levels are reached after 4–6 weeks of treatment. Miglustat is not significantly metabolized in humans and the major route of excretion is renal. In clinical trials, efficacy was demonstrated by significant reductions in liver and spleen volumes (12 and 19%, respectively) at 12 months and increase in hemoglobin and platelet count (0.91 g/dL and 13.6×109/l, respectively) at 24 months. Miglustat is generally well tolerated by patients and the most common side effects are diarrhea and weight loss.
• Uses: An alpha-glucosidase Inhibitor Treatment of glycolipid storage diseases.

Technology Process of N-BUTYLDEOXYNOJIRIMYCIN

There total 32 articles about N-BUTYLDEOXYNOJIRIMYCIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.5%

miglustat hydrochloride (210110-90-0,355012-88-3) → N-butyldeoxynojirimycin (72599-27-0,155501-85-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene;

Reference yield: 91.0%

N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol (227932-82-3) → N-butyldeoxynojirimycin (72599-27-0,155501-85-2)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; at -78 ℃; for 2.5h;

DOI:10.1055/s-1999-3430

Reference yield: 76.0%

1-bromo-butane (109-65-9) + 1,5-dideoxy-1,5-imino-D-glucitol (19130-96-2) → N-butyldeoxynojirimycin (72599-27-0,155501-85-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 - 90 ℃; for 24h;

DOI:10.1016/j.carres.2016.09.003

upstream raw materials:

D-xylo-hexos-5-ulose

N-butylamine

1-bromo-butane

1,5-dideoxy-1,5-imino-D-glucitol

Refernces

• 1、 Lahav, Dani?l,Liu, Bing,Van Den Berg, Richard J.B.H.N.,Van Den Nieuwendijk, Adrianus M. C. H.,Wennekes, Tom,Ghisaidoobe, Amar T.,Breen, Imogen,Ferraz, Maria J.,Kuo, Chi-Lin,Wu, Liang,Geurink, Paul P.,Ovaa, Huib,Van Der Marel, Gijsbert A.,Van Der Stelt, Mario,Boot, Rolf G.,Davies, Gideon J.,Aerts, Johannes M. F. G.,Overkleeft, Herman S.. "A Fluorescence Polarization Activity-Based Protein Profiling Assay in the Discovery of Potent, Selective Inhibitors for Human Nonlysosomal Glucosylceramidase". supporting information. p. 14192 - 14197. Retrieved 2017/10/17.
• 2、 Wang, Jiajia,Zhao, Yunyan,Zhao, Wei,Wang, Peng,Li, Jing. "Total synthesis of N-butyl-1-deoxynojirimycin". . p. 445 - 454. Retrieved 2017/08/23.