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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17NO4S2
Molecular Weight 387.473
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAROPARCIL

SMILES

O[C@@H]1CS[C@@H](SC2=CC=C(C=C2)C(=O)C3=CC=C(C=C3)C#N)[C@H](O)[C@H]1O

InChI

InChIKey=IMAFEPKOGMHYNH-LULLPPNCSA-N
InChI=1S/C19H17NO4S2/c20-9-11-1-3-12(4-2-11)16(22)13-5-7-14(8-6-13)26-19-18(24)17(23)15(21)10-25-19/h1-8,15,17-19,21,23-24H,10H2/t15-,17+,18-,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H17NO4S2
Molecular Weight 387.473
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Naroparcil [LF 90055], the lead compound in a series of orally-active antithrombotics, is an analogue of LF 1351, a compound shown to have antithrombotic action. Antithrombotic activity of naroparcil is dependent on modification in the plasma GAG profile which inactivates thrombin via heparin cofactor II (HCII).

Approval Year

PubMed

PubMed

TitleDatePubMed
The venous antithrombotic profile of naroparcil in the rabbit.
1994 Dec
Reduction of intimal hyperplasia by naroparcil, a 4-methylumbelliferyl beta-D-xyloside analogue, after arterial injury in the hypercholesterolemic rabbit.
1995 Nov
Further studies on the mechanism for the antithrombotic effects of naroparcil, an orally active thiozyloside compound.
1999 Jun
Patents

Patents

Sample Use Guides

The venous antithrombotic profile of naroparcil or (4-[4-cyanobenzoyl]-phenyl)-1.5-dithio-beta-D-xylopyranoside was investigated in the rabbit following single i.v. and oral administration. Naroparcil attenuated thrombus development in a Wessler stasis model of venous thrombosis (jugular vein) employing bovine factor Xa as a thrombogenic stimulus giving ED50 values of 21.9 mg/kg and 36.0 mg/kg after respectively i.v. and oral administration. Venous antithrombotic activity was maximal 2-3 h after i.v. administration and 4-8 h after oral administration. Four hours after the oral administration of maximal antithrombotic (Wessler model, factor Xa) doses (100 and 400 mg/kg), naroparcil had no significant effect on bleeding time. In platelet poor plasma obtained from animals treated 4 h previously with various doses. A sensitized thrombin time (to about 35 s) was modestly but significantly increased following oral administration of the compound at 400 mg/kg.
Route of Administration: Other
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:55:49 GMT 2023
Edited
by admin
on Fri Dec 15 15:55:49 GMT 2023
Record UNII
238M5105OY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAROPARCIL
INN  
INN  
Official Name English
naroparcil [INN]
Common Name English
P-(P-((5-THIO-.BETA.-D-XYLOPYRANOSYL)THIO)BENZOYL)BENZONITRILE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29750
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C66219
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
PUBCHEM
3047782
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
CAS
120819-70-7
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
SMS_ID
100000080322
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
FDA UNII
238M5105OY
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106685
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
MESH
C092014
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
EVMPD
SUB09166MIG
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
INN
6577
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY