Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H27NO6 |
Molecular Weight | 305.3673 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(O[C@]2([H])OC(C)(C)O[C@]2([H])[C@H]1OCCCN(C)C)[C@H](O)CO
InChI
InChIKey=YXBQLONCIPUQKO-UJPOAAIJSA-N
InChI=1S/C14H27NO6/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/t9-,10-,11+,12-,13-/m1/s1
Molecular Formula | C14H27NO6 |
Molecular Weight | 305.3673 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6806 mg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175698/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
AMIPRILOSE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
361 ng × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175698/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
AMIPRILOSE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
244 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175698/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
AMIPRILOSE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
95% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175698/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
AMIPRILOSE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
6 g 1 times / day multiple, oral (unknown) Studied dose Dose: 6 g, 1 times / day Route: oral Route: multiple Dose: 6 g, 1 times / day Sources: |
unhealthy n = 98 Health Status: unhealthy Condition: rheumatoid arthritis Sex: M+F Food Status: UNKNOWN Population Size: 98 Sources: |
Disc. AE: Visual disturbance, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Visual disturbance (2 patients) Sources: Thrombocytopenia (1 pt) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Thrombocytopenia | 1 pt Disc. AE |
6 g 1 times / day multiple, oral (unknown) Studied dose Dose: 6 g, 1 times / day Route: oral Route: multiple Dose: 6 g, 1 times / day Sources: |
unhealthy n = 98 Health Status: unhealthy Condition: rheumatoid arthritis Sex: M+F Food Status: UNKNOWN Population Size: 98 Sources: |
Visual disturbance | 2 patients Disc. AE |
6 g 1 times / day multiple, oral (unknown) Studied dose Dose: 6 g, 1 times / day Route: oral Route: multiple Dose: 6 g, 1 times / day Sources: |
unhealthy n = 98 Health Status: unhealthy Condition: rheumatoid arthritis Sex: M+F Food Status: UNKNOWN Population Size: 98 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Interleukin 1 and 2 production in homosexual men: a controlled trial of therafectin (SM-1213), a possible immunomodulator. | 1986 |
|
Evaluation of a modified hexose sugar, amiprilose hydrochloride, in experimental models of synovitis. | 1989 Jan |
|
Amiprilose hydrochloride for rheumatoid arthritis. | 1989 Sep 15 |
|
Amiprilose hydrochloride for the treatment of rheumatoid arthritis. | 2000 Feb |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2672925
amiprilose HCl, 6 g/d, or placebo for 12 weeks
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7695482
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
Created
by
admin
on
Edited
Fri Dec 15 16:09:59 GMT 2023
by
admin
on
Fri Dec 15 16:09:59 GMT 2023
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Record UNII |
S0FG5X68QT
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C257
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5958
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C76690
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56824-20-5
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CHEMBL1316321
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m1750
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C018424
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100000087232
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