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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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C E Brinckerhoff
Agents and actions, 30(3-4), 322-328 (1990-06-01)
Amiprilose hydrochloride, a modified hexose sugar effectively decreases proliferation of human skin and synovial fibroblasts and of rabbit synovial fibroblasts. It also decreases production of the inflammatory mediator prostaglandin E2 (PGE2) by these cells. Cell proliferation, measured by incorporation of
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
G Spencer-Green
Postgraduate medicine, 93(7), 129-140 (1993-05-15)
Nonsteroidal anti-inflammatory drugs comprise an important class of medications that reduce the signs and symptoms of osteoarthritis and rheumatoid arthritis. They bring relief to millions of people but do not eliminate underlying disease. Disease-modifying antirheumatic drugs also bring relief, but
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
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