927881-99-0
Chemical Structure
Rivipansel
Synonym(s): GMI-1070
- CAS No.: 927881-99-0
- Formula:C58H74N6O31S3
- Molecular Weight:1447.42
IUPAC Name: (S)-2-(((2R,3R,4S,5S,6R)-3-(benzoyloxy)-2-(((1R,2R,3S,5R)-3-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-5-((2-(2-(2-(2-oxo-2-((3,6,8-trisulfonaphthalen-1-yl)amino)ethoxy)ethoxy)acetamido)ethyl)carbamoyl)-2-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)cyclohexyl)oxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-3-cyclohexylpropanoic acid
InChIKey: VXBNTHRZPJLRSS-PTCSXESPSA-N
SMILES: O=C([C@H]1C[C@H]([C@@H]([C@H](C1)NC(C2=CC(NC(N2)=O)=O)=O)O[C@H]3[C@H]([C@@H]([C@@H]([C@@H](O3)C)O)O)O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O[C@H](C(O)=O)CC5CCCCC5)OC(C6=CC=CC=C6)=O)NCCNC(COCCOCC(NC7=CC(S(=O)(O)=O)=CC8=C7C(S(=O)(O)=O)=CC(S(=O)(O)=O)=C8)=O)=O
Biological Activity: Rivipansel is a small-molecule glycomimetic pan-selectin antagonist with inhibitory activity against E-selectin and P-selectin. Rivipansel binds tightly to the lectin domain of E-selectin, and selectively blocks the recognition of CD62L by E-selectin without affecting the binding of PSGL-1 to E-selectin. Rivipansel functionally inhibits the adhesion of hematopoietic cells to endothelial cells, and is applicable to research related to sickle cell disease[1][2].
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Rivipansel | Rivipansel is a small-molecule glycomimetic pan-selectin antagonist with inhibitory activity against E-selectin and P-selectin. Rivipansel binds tightly to the lectin domain of E-selectin, and selectively blocks the recognition of CD62L by E-selectin without affecting the binding of PSGL-1 to E-selectin. Rivipansel functionally inhibits the adhesion of hematopoietic cells to endothelial cells, and is applicable to research related to sickle cell disease. | |||||||||||||||||||||
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References
- [1]. Reema Jasuja, et al. Rivipansel: A Small Pan-Selectin Antagonist Improves Cerebral Perfusion and Inhibits Leukocyte Adhesion and in Murine Sickle Cell Disease Model. Blood (2016) 128 (22): 270.
- [2]. Scott I Simon, et al. Rivipansel (GMI-1070) Inhibits E-Selectin Recognition of Sialyl LewisX Expressed on CD62L (L-selectin) and Blocks Integrin Activation and Arrest of Human Neutrophils. Blood (2016) 128 (22): 2509.
