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A4687

Sigma-Aldrich

Amiprilose hydrochloride

Synonym(s):

1,2-O-Isopropylidene-3-O-[3′-(N,N-dimethylamino)propyl]-α-D-glucofuranose hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C14H27NO6 · HCl
CAS Number:
56824-20-5
Molecular Weight:
341.83
MDL number:
MFCD00133070
UNSPSC Code:
12352200
PubChem Substance ID:
24278217

storage temp.

2-8°C

SMILES string

Cl[H].[H][C@@]1(O[C@@H]2OC(C)(C)O[C@@H]2[C@H]1OCCCN(C)C)[C@H](O)CO

Biochem/physiol Actions

A synthetic carbohydrate shown to be a immunomodulator and anti-viral agent. Used as therapeutic agent in inflammatory arthritis. Regulatory effects on cytokines have been demonstrated in vitro. In vivo treatment of mice results in modulation of eicosanoid synthesis in part through the regulation of PLA2 activity.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
052H4053

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M R Young
Prostaglandins, 40(1), 35-49 (1990-07-01)
The modified hexose sugar, amiprilose HCl [1,2-O-isopropylinine-3-O-3'-(N',N'-dimethylamino-n-propyl)-D-g lucufuranose hydrochloride], has previously been shown to have antiinflammatory activities. The present study assessed whether eicosanoid biosynthesis is regulated by amiprilose HCl and whether the regulation is influenced at the early stage of
C O Siegel et al.
Artery, 21(2), 114-123 (1994-01-01)
The effect of amiprilose hydrochloride, a synthetic monosaccharide, on smooth muscle cell proliferation was studied in vitro. Using porcine aortic smooth muscle cell cultures, amiprilose significantly inhibited cell proliferation in a dose-dependent fashion at concentrations of 0.5-1.0 mg/ml. This antiproliferative
D M Chang
Immunopharmacology and immunotoxicology, 17(3), 437-450 (1995-08-01)
Investigative attempts to identify novel therapy for inflammatory connective tissue diseases continue to evolve. Amiprilose hydrochloride (amiprilose HCl) is a synthetic carbohydrate shown to have anti-inflammatory effects in animal models of inflammatory arthritis and in a multicenter clinical trial. Interleukin-1
P A Merkel et al.
Rheumatic diseases clinics of North America, 21(3), 779-796 (1995-08-01)
Agents ranging from simple analgesics to antiinflammatory drugs to powerful immunomodulators have been used for the treatment of rheumatoid arthritis with varying success. Despite the availability of agents that are believed to be "second line" or "disease modifying," many patients
E R Garrett et al.
Journal of pharmaceutical sciences, 72(9), 1045-1057 (1983-09-01)
The pharmacokinetics of 1,2-O-isopropylidene-3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucofuranose hydrochloride (1) was studied in dogs at intravenous and oral doses of 1-50 mg/kg. There was no significant difference between the electron-capture GLC of the heptafluorobutyric derivative of I and the radiochemical assay of chloroform extracts
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