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Details

Stereochemistry ACHIRAL
Molecular Formula C12H11Cl2N3O
Molecular Weight 284.141
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RAFIGRELIDE

SMILES

CC1(C)N2CC3=C(NC2=NC1=O)C=CC(Cl)=C3Cl

InChI

InChIKey=IGMDPBNGNRHCRW-UHFFFAOYSA-N
InChI=1S/C12H11Cl2N3O/c1-12(2)10(18)16-11-15-8-4-3-7(13)9(14)6(8)5-17(11)12/h3-4H,5H2,1-2H3,(H,15,16,18)

HIDE SMILES / InChI

Molecular Formula C12H11Cl2N3O
Molecular Weight 284.141
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Rafigrelide is an imidazoquinazoline derivative patented by pharmaceutical company Shire LLC as platelet-lowering agent for the treatment of myeloproliferative diseases. Rafigrelide is a chemical analog of anagrelide, which is used to reduce platelet counts in myeloproliferative disorders. Compared with anagrelide, Rafigrelide has reduced potency against phosphodiesterase III, which may help to reduce potential side effects. The concentration of Rafigrelide that produces 50% of the maximum inhibition (IC50) of PDE III is 164 nM, making it an approximately 200-fold less potent inhibitor of phosphodiesterase III than 3-hydroxy anagrelide. In the clinical trial, Rafigrelide showed antithrombotic properties during a two-week treatment period in healthy male volunteers. The reductions in thrombus formation were seen in surrogate models of both high and low shear rates suggesting drug efficacy in different arterial conditions.

Approval Year

PubMed

PubMed

TitleDatePubMed
Antithrombotic properties of rafigrelide: a phase 1, open-label, non-randomised, single-sequence, crossover study.
2014 Jul 3
Patents

Sample Use Guides

4 mg/day for 14 days
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:01:24 UTC 2023
Edited
by admin
on Sat Dec 16 18:01:24 UTC 2023
Record UNII
V8Q1Z0GK92
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RAFIGRELIDE
INN   WHO-DD  
INN  
Official Name English
Rafigrelide [WHO-DD]
Common Name English
3,3-DIMETHYLANAGRELIDE
Common Name English
rafigrelide [INN]
Common Name English
6,7-DICHLORO-3,3-DIMETHYL-5,10-DIHYDROIMIDAZO(2,1-B)QUINAZOLIN-2(3H)-ONE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1327
Created by admin on Sat Dec 16 18:01:24 UTC 2023 , Edited by admin on Sat Dec 16 18:01:24 UTC 2023
Code System Code Type Description
FDA UNII
V8Q1Z0GK92
Created by admin on Sat Dec 16 18:01:24 UTC 2023 , Edited by admin on Sat Dec 16 18:01:24 UTC 2023
PRIMARY
PUBCHEM
135564921
Created by admin on Sat Dec 16 18:01:24 UTC 2023 , Edited by admin on Sat Dec 16 18:01:24 UTC 2023
PRIMARY
NCI_THESAURUS
C152145
Created by admin on Sat Dec 16 18:01:24 UTC 2023 , Edited by admin on Sat Dec 16 18:01:24 UTC 2023
PRIMARY
CAS
1029711-88-3
Created by admin on Sat Dec 16 18:01:24 UTC 2023 , Edited by admin on Sat Dec 16 18:01:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID30145594
Created by admin on Sat Dec 16 18:01:24 UTC 2023 , Edited by admin on Sat Dec 16 18:01:24 UTC 2023
PRIMARY
SMS_ID
300000036844
Created by admin on Sat Dec 16 18:01:24 UTC 2023 , Edited by admin on Sat Dec 16 18:01:24 UTC 2023
PRIMARY
INN
9494
Created by admin on Sat Dec 16 18:01:24 UTC 2023 , Edited by admin on Sat Dec 16 18:01:24 UTC 2023
PRIMARY
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OFF-TARGET->INHIBITOR
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ACTIVE MOIETY