AMIPRILOSE

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 Search

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

Description
Sources: https://www.thepharmaletter.com/article/therafectin-enters-phase-iii-for-ra | https://www.ncbi.nlm.nih.gov/pubmed/19078443

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

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19078443	Primary		Phase III 656	Therafectin Approved Use Unknown

C_max

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

T_1/2

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

F_unbound

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: https://pubmed.ncbi.nlm.nih.gov/2672925	unhealthy n = 98 Health Status: unhealthy Condition: rheumatoid arthritis Sex: M+F Food Status: UNKNOWN Population Size: 98 Sources: https://pubmed.ncbi.nlm.nih.gov/2672925	Disc. AE: Visual disturbance, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Visual disturbance (2 patients) Thrombocytopenia (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/2672925

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: https://pubmed.ncbi.nlm.nih.gov/2672925	unhealthy n = 98 Health Status: unhealthy Condition: rheumatoid arthritis Sex: M+F Food Status: UNKNOWN Population Size: 98 Sources: https://pubmed.ncbi.nlm.nih.gov/2672925
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: https://pubmed.ncbi.nlm.nih.gov/2672925	unhealthy n = 98 Health Status: unhealthy Condition: rheumatoid arthritis Sex: M+F Food Status: UNKNOWN Population Size: 98 Sources: https://pubmed.ncbi.nlm.nih.gov/2672925

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY115155	https://www.001chemical.com/chem/search?q=DY115155
AK Scientific	V0471	https://aksci.com/item_detail.php?cat=V0471
Angene	AGN-PC-0SMFSL	http://www.angenechemical.com/productshow/AGN-PC-0SMFSL.html
BLD Pharm	BD53495	http://www.bldpharm.com/search/Search.html?keyword=BD53495
BOC Sciences	56824-20-5	http://www.bocsci.com/description.asp?cas=56824-20-5
BOC Sciences	60414-06-4	http://www.bocsci.com/description.asp?cas=60414-06-4
Matrix Scientific	99473	http://www.matrixscientific.com/099473.html
Molcore	MC115155	http://www.molcore.com/CatMC115155.html
Tetrahedron	TS09169	http://www.thsci.com/search.do?q=TS09169
Toronto Research Chemicals	A400305	https://www.trc-canada.com/product-detail/?CatNum=A400305
eMolecules	252313780	https://orderbb.emolecules.com/search/#?query=252313780
eMolecules	44690804	https://orderbb.emolecules.com/search/#?query=44690804

PubMed

Title	Date	PubMed
Interleukin 1 and 2 production in homosexual men: a controlled trial of therafectin (SM-1213), a possible immunomodulator.	1986	2940301
Evaluation of a modified hexose sugar, amiprilose hydrochloride, in experimental models of synovitis.	1989 Jan	2785600
Amiprilose hydrochloride for rheumatoid arthritis.	1989 Sep 15	2672925
Amiprilose hydrochloride for the treatment of rheumatoid arthritis.	2000 Feb	19078443

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.

Name

Type

Language

AMIPRILOSE

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