CARAFIBAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H27N5O5
Molecular Weight	465.5017
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)C[C@H](NC(=O)CN1C(=O)N[C@](C)(C1=O)C2=CC=C(C=C2)C(N)=N)C3=CC=CC=C3

InChI

InChIKey=SSGOEPXWNBXKPQ-UUOWRZLLSA-N

InChI=1S/C24H27N5O5/c1-3-34-20(31)13-18(15-7-5-4-6-8-15)27-19(30)14-29-22(32)24(2,28-23(29)33)17-11-9-16(10-12-17)21(25)26/h4-12,18H,3,13-14H2,1-2H3,(H3,25,26)(H,27,30)(H,28,33)/t18-,24-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11312916 | Bulletin des Societes Chimiques Belges (1996), 105, (10-11), 711-719.

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

Approval Year

PubMed

Title	Date	PubMed
Discovery of an orally active non-peptide fibrinogen receptor antagonist based on the hydantoin scaffold.	2001 Apr 12	11312916

Patents

Name

Type

Language

CARAFIBAN

Official Name

English

ETHYL (S)-.BETA.-(2-((S)-4-(P-AMIDINOPHENYL)-4-METHYL-2,5-DIOXO-1-IMIDAZOLIDINYL)ACETAMIDO)HYDROCINNAMATE

Common Name

English

carafiban [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29750