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Deoxygalactonojirimycin Hydrochloride

CAS No.
75172-81-5
Chemical Name:
Deoxygalactonojirimycin Hydrochloride
Synonyms
DGJ;Amigal;GR181413A;GR-181413A;GR 181413A;5-Dideoxy-1;Migalastat HCl;Unii-cly7m0xd20;GALACTOSTATIN HCL;DGJ, HYDROCHLORIDE
CBNumber:
CB5252941
Molecular Formula:
C6H13NO4.ClH
Molecular Weight:
199.63
MDL Number:
MFCD00269962
MOL File:
75172-81-5.mol
Last updated:2024-07-17 18:13:28

Deoxygalactonojirimycin Hydrochloride Properties

Melting point 260
storage temp. 2-8°C
solubility Methanol (Slightly), Water (Slightly)
form White crystalline solid
color White to Brown
FDA UNII CLY7M0XD20

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P280-P301+P312-P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
Hazard Note  Irritant
HS Code  29333990
NFPA 704
0
2 0

Deoxygalactonojirimycin Hydrochloride price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D9641 Deoxygalactonojirimycin hydrochloride 75172-81-5 2mg $163 2024-03-01 Buy
Sigma-Aldrich 259544 Deoxygalactonojirimycin, Hydrochloride Potent and selective α-galactosidase inhibitor. 75172-81-5 5mg $259 2022-05-15 Buy
Cayman Chemical 17179 1-Deoxygalactonojirimycin (hydrochloride) ≥98% 75172-81-5 1mg $44 2024-03-01 Buy
Cayman Chemical 17179 1-Deoxygalactonojirimycin (hydrochloride) ≥98% 75172-81-5 5mg $140 2024-03-01 Buy
Cayman Chemical 17179 1-Deoxygalactonojirimycin (hydrochloride) ≥98% 75172-81-5 10mg $235 2024-03-01 Buy
Product number Packaging Price Buy
D9641 2mg $163 Buy
259544 5mg $259 Buy
17179 1mg $44 Buy
17179 5mg $140 Buy
17179 10mg $235 Buy

Deoxygalactonojirimycin Hydrochloride Chemical Properties,Uses,Production

Description

Migalastat, which is marketed by Amicus Therapeutics, received approval in the EU for the treatment of Fabry disease in adults and adolescents aged 16 or older. Fabry disease is caused by mutations of the enzyme α-galactosidase A (α-GAL A) that cause protein misfolding and prevents efficient metabolism of the glycosphingolipid globotriaosylceramide (GL3). Accumulation of GL3 in lysosomes, blood vessels, and various tissues ultimately leads to significant heart, kidney, and dermatological problems. Migalastat functions as a molecular chaperone to α- GAL A, engaging the enzyme and enabling it to adopt the proper conformation allowing for efficient breakdown of GL3. Because the standard of care prior to 2016 for treating Fabry disease was enzyme replacement therapy (ERT), migalastat’s approval in the EU represents an important advance for patients suffering from this disorder.

Chemical Properties

White Crystalline Solid

Uses

Deoxygalactonojirimycin hydrochloride has been used as an α-galactosidase A inhibitor to assess the enzymatic activity of α-galactosidase A. It has also been used as an α-galactosidase A inhibitor to study its effects on the mRNA levels in human embryonic kidney (HEK) cells and hippocampal neurons.

Uses

Proven to be an extremely potent and selective a-D-galactosidase inhibitor.

Uses

inhibitor of b-glucosidase

brand name

Treatment of Fabry disease.

Biochem/physiol Actions

Deoxygalactonojirimycin hydrochloride is an inhibitor of α-galactosidase A. Deoxygalactonojirimycin exhibits therapeutic effects against Fabry disease.

Synthesis

Several unique synthetic approaches to migalastat, which is also known as D-1-deoxygalactonojirimycin (DGJ), have been reported in the literature. Although the most likely commercial-scale preparation of this drug proceeds through a microbial fermentation process disclosed in a 2015 patent, a kilogram-scale synthesis of the drug outlined has been described in a 2008 patent application filed by Amicus. This route closely resembles a procedure disclosed in 1999 by Uriel and Santoyo-Gonzalez that presented handling and safety concerns. Commercial D-galactose (143) was treated with five equivalents of pivaloyl imidazole (144), followed by triflation, treatment with Hunig?ˉs base, and exposure to sodium nitrite to furnish the tetrapivaloyl altofuranose triflate 145 after recrystallization from heptane. Next, stereospecific azide displacement of the triflate successfully delivered azidofuranose 146 in 65-70% yield. This reaction generated over 3 kg of the desired alkyl azide after recrystallization from ethanol and water. Lastly, palladium-catalyzed hydrogenolysis in the presence of sodium methoxide, a methanolic acidification step, and then a subsequent acidification step using HCl in THF furnished migalastat hydrochloride (XV) in 70-75% yield over the three-step sequence from 146. Synthesis_75172-81-5

target

α-galactosidase

IC 50

40 nm

References

[1] asano n, ishii s, kizu h, et al. in vitro inhibition and intracellular enhancement of lysosomal α‐galactosidase a activity in fabry lymphoblasts by 1‐deoxygalactonojirimycin and its derivatives[j]. febs journal, 2000, 267(13): 4179-4186.
[2] ishii s, chang h, yoshioka h, et al. preclinical efficacy and safety of 1-deoxygalactonojirimycin in mice for fabry disease[j]. journal of pharmacology and experimental therapeutics, 2009, 328(3): 723-731.

Deoxygalactonojirimycin Hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

Deoxygalactonojirimycin Hydrochloride Suppliers

Global( 92)Suppliers
Supplier Tel Email Country ProdList Advantage
NewCan Biotech Limited
+86-0571-86912261 +8613735419629 sales@newcanbio.com China 9980 58
career henan chemical co
+86-0371-86658258 +8613203830695 sales@coreychem.com China 29888 58
Jinan Carbotang Biotech Co.,Ltd.
+8615866703830 figo.gao@foxmail.com China 7621 58
BOC Sciences
+1-631-485-4226 inquiry@bocsci.com United States 19553 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 19892 58
Shanxi Xuanran Import and Export Trade Co., Ltd.
+8617735180244 mike_yan@xuanranglobal.com CHINA 4022 58
Finetech Industry Limited
+86-27-87465837 +8618971612321 info@finetechnology-ind.com China 9640 58
Wuhan Fortuna Chemical Co., Ltd
+86-027-59207850 info@fortunachem.com China 5987 58
InvivoChem
+1-708-310-1919 +1-13798911105 sales@invivochem.cn United States 6393 58
LEAPCHEM CO., LTD.
+86-852-30606658 market18@leapchem.com China 43348 58

View Lastest Price from Deoxygalactonojirimycin Hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Migalastat HCl pictures 2024-09-18 Migalastat HCl
75172-81-5
US $0.00 / G 10G 98%min 30kg/month WUHAN FORTUNA CHEMICAL CO., LTD
Migalastat Hydrochloride pictures 2024-07-17 Migalastat Hydrochloride
75172-81-5
US $0.00-0.00 / g 1g 98% 10kg NewCan Biotech Limited
DEOXYGALACTONOJIRIMYCIN, HYDROCHLORIDE pictures 2019-09-11 DEOXYGALACTONOJIRIMYCIN, HYDROCHLORIDE
75172-81-5
US $1.00 / KG 1KG 98 200kg Career Henan Chemical Co
  • Migalastat HCl pictures
  • Migalastat HCl
    75172-81-5
  • US $0.00 / G
  • 98%min
  • WUHAN FORTUNA CHEMICAL CO., LTD
1,5-DIDEOXY-1,5-IMINO-D-GALACTITOL, HYDROCHLORIDE 1-DEOXYGALACTONOJIRIMYCIN HCL DEOXYGALACTONOJIRIMYCIN HCL DEOXYGALACTONOJIRIMYCIN, HYDROCHLORIDE DGJ DGJ, HYDROCHLORIDE GALACTOSTATIN HCL 3,4,5-Piperidinetriol, 2-(hydroxymethyl)-, hydrochloride, (2R,3S,4R,5S)- 1,5-dideoxy-1,5-imino-d-galactitol Galactostatin hydrochloride Amigal Migalastat hydrochloride Unii-cly7m0xd20 1-Deoxygalactonojirimycin Hydrochloride (2R,3S,4R,5S)-2-(Hydroxymethyl)piperidine-3,4,5-triol hydrochloride Galactostatin hydrochloride, Deoxygalactonojirimycin hydrochloride (2R,3S,4R,5S)-2-HydroxyMethyl-3,4,5-piperidinetriol Hydrochloride 1-Deoxygalactostatin Hydrochloride Migalastat HCl GR181413A GR-181413A Deoxygalactonojirimycin, Hydrochloride - CAS 75172-81-5 - Calbiochem 1-Deoxygalactonojirimycin, hydrochloride, Min. 98% GR 181413A AT1001; AT 1001; AT-1001; GR181413A; GR 181413A; GR-181413A; 1;5-DIDEOXY-1;5-IMINO-D-GALACTITOL; 1-DEOXYGALACTONOJIRIMYCIN; 1-DEOXYGALACTOSTATIN; AMIGAL; MIGALASTAT 5-imino-D-galactitol 5-Dideoxy-1 3,4,5-Piperidinetriol, 2-(hydroxymethyl)-, hydrochloride (1:1), (2R,3S,4R,5S)- 75172-81-5 C6H13NO4ClH Enzymes, Inhibitors, and Substrates Enzyme Inhibitors Enzyme Inhibitors by Enzyme D to K Galactosidase, alpha- BioChemical Biochemicals and Reagents 13C & 2H Sugars Carbohydrates & Derivatives Glycosidase Inhibitors Inhibitors