Sibrafiban

Chemical compound

Sibrafiban
Identifiers

IUPAC name [Z]-(S)-[[1-[2-[[4-(amino-hydroxyiminomethyl)-benzoyl]amino]-1-oxopropyl]-4-piperidinyl]oxyl]-acetic ethyl ester
CAS Number	170094-62-9^Y
PubChem CID	5491394
ChemSpider	4590509
UNII	YUE443B0NF
KEGG	D05834
ChEMBL	ChEMBL435176
CompTox Dashboard (EPA)	DTXSID90938247
Chemical and physical data
Formula	C₂₀H₂₈N₄O₆
Molar mass	420.466 g·mol⁻¹
3D model (JSmol)	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).^[1] 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 with acute coronary syndrome. The development of sibrafiban was terminated.

References

^ Dooley M, Goa KL (February 1999). "Sibrafiban". Drugs. 57 (2): 225–30, discussion 231–2. doi:10.2165/00003495-199957020-00012. PMID 10188763. S2CID 263996772.

Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)

Antiplatelet drugs

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