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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H23N5O5
Molecular Weight 437.4485
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of des-ethyl- Carafiban

SMILES

C[C@]1(NC(=O)N(CC(=O)N[C@@H](CC(O)=O)C2=CC=CC=C2)C1=O)C3=CC=C(C=C3)C(N)=N

InChI

InChIKey=BQTUWUXJPAYSPB-AOMKIAJQSA-N
InChI=1S/C22H23N5O5/c1-22(15-9-7-14(8-10-15)19(23)24)20(31)27(21(32)26-22)12-17(28)25-16(11-18(29)30)13-5-3-2-4-6-13/h2-10,16H,11-12H2,1H3,(H3,23,24)(H,25,28)(H,26,32)(H,29,30)/t16-,22-/m0/s1

HIDE SMILES / InChI
Carafiban is orally active heterocyclic peptide mimetics fibrinogen IIb/IIIa receptor antagonist with antithrombotic activity. Carafiban is a prodrug, that underwent metabolic transformation to active metabolite des-ethyl- Carafiban, that inhibited dose-dependently and reversibly human platelet aggregation. In conscious dogs, Carafiban showed a high plasma availability of the active moiety of 42±8% and a plasma half-life of 9.9 h after oral administration as measured by bioassay. Carafiban may potentially be used for chronic treatment and prophylaxis of thrombotic diseases in humans.

Originator

Sources: Bulletin des Societes Chimiques Belges (1996), 105, (10-11), 711-719.

Approval Year

PubMed

PubMed

TitleDatePubMed
Discovery of an orally active non-peptide fibrinogen receptor antagonist based on the hydantoin scaffold.
2001 Apr 12
Patents

Patents

Name Type Language
des-ethyl- Carafiban
Common Name English
Benzenepropanoic acid, β-[[[4-[4-(aminoiminomethyl)phenyl]-4-methyl-2,5-dioxo-1-imidazolidinyl]acetyl]amino]-, [S-(R*,R*)]-
Systematic Name English
(3S)-3-{2-[(4S)-4-(4-carbamimidoylphenyl)-4-methyl-2,5-dioxoimidazolidin-1-yl]acetamido}-3-phenylpropanoic acid
Systematic Name English
Code System Code Type Description
PUBCHEM
9912737
Created by admin on Sat Dec 16 19:49:54 UTC 2023 , Edited by admin on Sat Dec 16 19:49:54 UTC 2023
PRIMARY
CAS
170565-45-4
Created by admin on Sat Dec 16 19:49:54 UTC 2023 , Edited by admin on Sat Dec 16 19:49:54 UTC 2023
PRIMARY
FDA UNII
Q9GG3H64D2
Created by admin on Sat Dec 16 19:49:54 UTC 2023 , Edited by admin on Sat Dec 16 19:49:54 UTC 2023
PRIMARY