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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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Garrett, E.R., et al.
Journal of Pharmacological Sciences, 71, 387-387 (1982)
R I Kieval et al.
The Journal of rheumatology, 16(1), 67-74 (1989-01-01)
Amiprilose HC1 (SM-1213), a nontoxic modified hexose sugar, was evaluated in in vivo and in vitro models of synovitis. In 8 sequential trials, 90 Louvain (LOU) rats and 91 Sprague-Dawley (SD) rats were immunized with chick type II collagen and
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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