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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H27NO6.ClH
Molecular Weight 341.828
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMIPRILOSE HYDROCHLORIDE

SMILES

Cl.CN(C)CCCO[C@H]1[C@H](O[C@@H]2OC(C)(C)O[C@H]12)[C@H](O)CO

InChI

InChIKey=RJNRORZRFGUAKL-ADMBVFOFSA-N
InChI=1S/C14H27NO6.ClH/c1-14(2)20-12-11(18-7-5-6-15(3)4)10(9(17)8-16)19-13(12)21-14;/h9-13,16-17H,5-8H2,1-4H3;1H/t9-,10-,11+,12-,13-;/m1./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C14H27NO6
Molecular Weight 305.3673
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Amiprilose hydrochloride (brand name Therafectin), a novel synthetic carbohydrate with anti-inflammatory properties, which was developed for the treatment of rheumatoid arthritis. In September 1993, FDA informed that this drug could not be approved because there was not adequate data demonstrating the drug’s effectiveness.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Therafectin

Cmax

ValueDoseCo-administeredAnalytePopulation
6806 mg/mL
100 mg single, intravenous
AMIPRILOSE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
361 ng × min/L
100 mg single, intravenous
AMIPRILOSE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
244 min
100 mg single, intravenous
AMIPRILOSE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
95%
100 mg single, intravenous
AMIPRILOSE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
amiprilose HCl, 6 g/d, or placebo for 12 weeks
Route of Administration: Oral
In Vitro Use Guide
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 effect was reversible upon removing amiprilose by cell washing and adding fresh media. Pretreating cells with amiprilose before serum stimulation did not affect subsequent growth. Inhibition of proliferation occurred when amiprilose was added up to 48 hours after serum stimulation.
Substance Class Chemical
Record UNII
546994B3VA
Record Status Validated (UNII)
Record Version