1,5-dideoxy-1,5-[[2-[4-(ethoxycarbonyl)phenoxy]ethyl]imino]-D-glucitol
1,5-dideoxy-1,5-[[2-[4-(ethoxycarbonyl)phenoxy]ethyl]imino]-D-glucitol Basic information
- Product Name:
- 1,5-dideoxy-1,5-[[2-[4-(ethoxycarbonyl)phenoxy]ethyl]imino]-D-glucitol
- Synonyms:
-
- 1,5-dideoxy-1,5-[[2-[4-(ethoxycarbonyl)phenoxy]ethyl]imino]-D-glucitol
- 4-[2-[(2R,3R,4R,5S)-3,4,5-Trihydroxy-2-(hydroxymethyl)piperidino]ethoxy]benzoic acid ethyl ester
- BAY-o-1248
- MKC-542
- Emiglitate
- Benzoic acid, 4-[2-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)-1-piperidinyl]ethoxy]-, ethyl ester
- 1,5-dideoxy-1,5-[[2-[4-(ethoxycarbonyl)phenoxy]ethyl]imino]-D-glucitol USP/EP/BP
- CAS:
- 80879-63-6
- MF:
- C17H25NO7
- MW:
- 355.38
- EINECS:
- 279-613-2
- Mol File:
- 80879-63-6.mol
1,5-dideoxy-1,5-[[2-[4-(ethoxycarbonyl)phenoxy]ethyl]imino]-D-glucitol Chemical Properties
- Boiling point:
- 580.2±50.0 °C(Predicted)
- Density
- 1.328±0.06 g/cm3(Predicted)
- storage temp.
- Store at -20°C
- solubility
- Soluble in DMSO
- form
- Solid
- pka
- 13.68±0.70(Predicted)
- color
- White to off-white
1,5-dideoxy-1,5-[[2-[4-(ethoxycarbonyl)phenoxy]ethyl]imino]-D-glucitol Usage And Synthesis
Description
Emiglitate (BAY O 1248), another deoxynojirimycin analogue is characterized by at least five-fold higher inhibitory potency than acarbose and additionally shows a long-lasting inhibitory effect. In animal studies emiglitate was still active up to 17 h after a single oral administration due to its pharmacokinetic behavior (formation of an active metabolite). Both miglitol and emiglitate differ in their pharmacokinetic behavior from acarbose, which is poorly absorbed (1 – 2 %). The deoxynojirimycin derivatives are structurally related to monosaccharides and will be absorbed in the jejunum.
Uses
Emiglitate (BAY o 1248) is a potent, selective and competitive inhibitor of α-glucoside hydrolase.
in vivo
In fasted rats, emiglitate inducec a significant, dose-dependent increase of hepatic glycogen concentrations. The increase in hepatic glycogen is due to lysosomal storage of glycogen only. Emiglitate in the amount of 5 mg/kg b.wt. does not induce significant changes either of glycogen concentrations or at the EM-level[2].
References
[1] Mosén H, et al. Nitric oxide inhibits, and carbon monoxide activates, islet acid alpha-glucoside hydrolase activitiesin parallel with glucose-stimulated insulin secretion. J Endocrinol. 2006 Sep;190(3):681-93. DOI:10.1677/joe.1.06890
[2] Lembcke B, et al. Lysosomal storage of glycogen as a sequel of alpha-glucosidase inhibition by the absorbed deoxynojirimycin derivative emiglitate (BAYo1248). A drug-induced pattern of hepatic glycogen storage mimicking Pompe's disease (glycogenosis type II). Res Exp Med (Berl). 1991;191(6):389-404. DOI:10.1007/BF02576694
1,5-dideoxy-1,5-[[2-[4-(ethoxycarbonyl)phenoxy]ethyl]imino]-D-glucitol Supplier
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1,5-dideoxy-1,5-[[2-[4-(ethoxycarbonyl)phenoxy]ethyl]imino]-D-glucitol (80879-63-6)Related Product Information
- Repaglinide
- Miglitol
- N-METHYL-1-DEOXYNOJIRIMYCIN
- 4-[2-(1-Piperidinyl)ethoxy]benzaldehyde
- 1,5-dideoxy-1,5-[[2-[4-(ethoxycarbonyl)phenoxy]ethyl]imino]-D-glucitol
- 1-Deoxynojirimycin
- N,N-BIS(2-HYDROXYETHYL)ISOPROPANOLAMINE
- DIETHANOL PROPANOLAMINE
- 4-[2-(DIMETHYLAMINO)ETHOXY]BENZALDEHYDE
- 4-(2-(DIETHYLAMINO)-ETHOXY)-BENZALDEHYDE
- 4-HYDROXY-1-PIPERIDINEETHANOL 96
- 1,5-DIDEOXY-1,5-IMINO-XYLITOL
- trans-3,4-Dihydroxypiperidine
- 4-(2-piperdinylethoxy)benzoic acid hydrochloride
- [4-[2-(DIMETHYLAMINO)ETHOXY]PHENYL]METHANOL
- 4-(2-AMINOETHOXY)BENZOIC ACID