U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of AMIPRILOSE

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

HIDE SMILES / InChI

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Therafectin

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6806 mg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
361 ng × min/L
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

T1/2

ValueDoseCo-administeredAnalytePopulation
244 min
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

Funbound

ValueDoseCo-administeredAnalytePopulation
95%
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

Doses

DosePopulationAdverse 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)
Thrombocytopenia (1 pt)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
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

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
Created
by admin
on Fri Dec 15 16:09:59 GMT 2023
Edited
by admin
on Fri Dec 15 16:09:59 GMT 2023
Record UNII
S0FG5X68QT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMIPRILOSE
INN   MI  
INN  
Official Name English
SM-1213
Code English
3-O-(3-(DIMETHYLAMINO)PROPYL)-1,2-O-ISOPROPYLIDENE-.ALPHA.-D-GLUCOFURANOSE
Common Name English
amiprilose [INN]
Common Name English
AMIPRILOSE [MI]
Common Name English
.ALPHA.-D-GLUCOFURANOSE, 3-O-(3-(DIMETHYLAMINO)PROPYL)-1,2-O-(1-METHYLETHYLIDENE)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
Code System Code Type Description
INN
5958
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
PRIMARY
NCI_THESAURUS
C76690
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
PRIMARY
CAS
56824-20-5
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
PRIMARY
FDA UNII
S0FG5X68QT
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL1316321
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
PRIMARY
PUBCHEM
121928
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
PRIMARY
EVMPD
SUB05455MIG
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID9048483
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
PRIMARY
MERCK INDEX
m1750
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
PRIMARY Merck Index
MESH
C018424
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
PRIMARY
SMS_ID
100000087232
Created by admin on Fri Dec 15 16:09:59 GMT 2023 , Edited by admin on Fri Dec 15 16:09:59 GMT 2023
PRIMARY
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