Deoxygalactonojirimycin Hydrochloride
- Product Name
- 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
- Formula Weight
- 199.63
- MOL File
- 75172-81-5.mol
Deoxygalactonojirimycin Hydrochloride Property
- Melting point:
- 260
- storage temp.
- 2-8°C
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- White crystalline solid
- color
- White to Brown
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- D9641
- Product name
- Deoxygalactonojirimycin hydrochloride
- Packaging
- 2mg
- Price
- $163
- Updated
- 2024/03/01
- Product number
- 259544
- Product name
- Deoxygalactonojirimycin, Hydrochloride
- Purity
- Potent and selective α-galactosidase inhibitor.
- Packaging
- 5mg
- Price
- $259
- Updated
- 2022/05/15
- Product number
- 17179
- Product name
- 1-Deoxygalactonojirimycin (hydrochloride)
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $44
- Updated
- 2024/03/01
- Product number
- 17179
- Product name
- 1-Deoxygalactonojirimycin (hydrochloride)
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $140
- Updated
- 2024/03/01
- Product number
- 17179
- Product name
- 1-Deoxygalactonojirimycin (hydrochloride)
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $235
- Updated
- 2024/03/01
Deoxygalactonojirimycin Hydrochloride Chemical Properties,Usage,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
Proven to be an extremely potent and selective a-D-galactosidase inhibitor.
Uses
inhibitor of b-glucosidase
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.
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.
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
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View Lastest Price from Deoxygalactonojirimycin Hydrochloride manufacturers
- Product
- Migalastat HCl 75172-81-5
- Price
- US $0.00/G
- Min. Order
- 10G
- Purity
- 98%min
- Supply Ability
- 30kg/month
- Release date
- 2023-02-15
- Product
- Migalastat Hydrochloride 75172-81-5
- Price
- US $0.00-0.00/g
- Min. Order
- 1g
- Purity
- 98%
- Supply Ability
- 10kg
- Release date
- 2024-07-17
- Product
- DEOXYGALACTONOJIRIMYCIN, HYDROCHLORIDE 75172-81-5
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 98
- Supply Ability
- 200kg
- Release date
- 2019-09-10