Sibrafiban

Sibrafiban
Identifiers

IUPAC name [Z]-(S)-[[1-[2-[[4-(amino-hydroxyiminomethyl)-benzoyl]amino]-1-oxopropyl]-4-piperidinyl]oxyl]-acetic ethyl ester
PubChem (CID)	5491394
ChemSpider	4590509
UNII	YUE443B0NF^Y
KEGG	D05834
ChEMBL	CHEMBL435176
Chemical and physical data
Formula	C₂₀H₂₈N₄O₆
Molar mass	420.46 g/mol
3D model (Jmol)	Interactive image
SMILES CCOC(=O)COC1CCN(CC1)C(=O)[C@H](C)NC(=O)c2ccc(cc2)C(=N)NO
InChI InChI=1S/C20H28N4O6/c1-3-29-17(25)12-30-16-8-10-24(11-9-16)20(27)13(2)22-19(26)15-6-4-14(5-7-15)18(21)23-28/h4-7,13,16,28H,3,8-12H2,1-2H3,(H2,21,23)(H,22,26)/t13-/m0/s1 Key:WBNUCLPUOSXSNJ-ZDUSSCGKSA-N

Sibrafiban (Ro 48-3657, proposed brand name Xubix) is the double prodrug of Ro-44-3888, which is a platelet aggregation inhibitor. It was being developed for secondary prevention of arterial thrombosis following unstable angina pectoris and acute myocardial infarction (MI). On August 6, 1999, Hoffmann-La Roche announced that the preliminary results from Phase III clinical trials had not shown that sibrafiban was better than aspirin in preventing recurrent ischemic events in patients suffering from acute coronary syndrome. The development of sibrafiban was terminated.

Glycoprotein IIb/IIIa inhibitors	Abciximab Eptifibatide Orbofiban Roxifiban Sibrafiban^§ Tirofiban

ADP receptor/P2Y₁₂ inhibitors	Thienopyridines Clopidogrel Prasugrel Ticlopidine Nucleotide/nucleoside analogs Cangrelor Elinogrel Ticagrelor

Prostaglandin analogue (PGI2)	Beraprost Iloprost Prostacyclin Treprostinil

COX inhibitors	Acetylsalicylic acid/Aspirin^# Aloxiprin Carbasalate calcium Indobufen Triflusal

Thromboxane inhibitors	Thromboxane synthase inhibitors Dipyridamole (+ aspirin) Picotamide Terbogrel Receptor antagonists Terbogrel Terutroban^§

Phosphodiesterase inhibitors	Cilostazol Dipyridamole Triflusal

Other	Cloricromen Ditazole Vorapaxar

Anticoagulants

Vitamin K antagonists
(inhibit II, VII, IX, X)

Factor Xa inhibitors
(with some II inhibition)

Heparin group/ glycosaminoglycans/ (bind antithrombin)	Low molecular weight heparin Bemiparin Certoparin Dalteparin Enoxaparin Nadroparin Parnaparin Reviparin Tinzaparin^‡ Oligosaccharides Fondaparinux Idraparinux^§ Heparinoids Danaparoid Dermatan sulfate Sulodexide

Direct Xa inhibitors ("xabans")	Apixaban Betrixaban^† Darexaban^§ Edoxaban Otamixaban^§ Rivaroxaban

Direct thrombin (IIa) inhibitors

Other

Thrombolytic drugs/
fibrinolytics

Non-medicinal

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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Sibrafiban

See also