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ristocetin

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Also known as ristomycin

Ristocetin is a glycopeptide antibiotic, obtained from Amycolatopsis lurida, previously used to treat staphylococcal infections. It is no longer used clinically because it caused thrombocytopenia and platelet agglutination. It is now used solely to assay those functions in vitro in the diagnosis of conditions such as von Willebrand disease (vWD) and Bernard–Soulier syndrome. Platelet agglutination caused by ristocetin can occur only in the presence of von Willebrand factor multimers, so if ristocetin is added to blood lacking the factor (or its receptor—see below), the platelets will not clump

Research

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Wikidata facts

Mass
2066.6615888
Show 5 more facts
canonical SMILES
CC1C(C(CC(O1)OC2C3C(=O)NC(C4=CC(=CC(=C4C5=C(C=CC(=C5)C(C(=O)N3)NC(=O)C6C7=CC(=C(C(=C7)OC8=CC=C2C=C8)OC9C(C(C(C(O9)COC1C(C(C(C(O1)C)O)O)O)O)O)OC1C(C(C(C(O1)CO)O)O)OC1C(C(C(CO1)O)O)O)OC1=CC=C(C=C1)C(C1C(=O)NC(C2=CC(=C(C(=C2)O)C)OC2=C(C=CC(=C2)C(C(=O)N1)N)O)C(=O)N6)O)O)OC1C(C(C(C(O1)CO)O)O)O)O)C(=O)O)N)O
chemical formula
C₉₄H₁₀₈N₈O₄₄
isomeric SMILES
COC(=O)[C@H]1NC(=O)[C@H]2NC(=O)[C@H](NC(=O)[C@@H]3NC(=O)[C@H]4NC(=O)[C@H](NC(=O)[C@H](N)c5ccc(O)c(c5)Oc5cc4cc(O)c5C)[C@H](O)c4ccc(cc4)Oc4cc3cc(c4O[C@@H]3O[C@H](COC4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@@H](CO)[C@H](O)[C@@H](O)[C@H]3O[C@@H]3OC[C@@H](O)[C@@H](O)[C@@H]3O)Oc3ccc(cc3)[C@H]2O[C@@H]2C[C@@H](N)[C@@H](O)[C@H](C)O2)c2ccc(O)c(c2)-c2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)cc(O)cc21
subject has role
antibiotic
found in taxon
Nocardia
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Encyclopedic overview

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Ristocetin is a glycopeptide antibiotic, obtained from Amycolatopsis lurida, previously used to treat staphylococcal infections. It is no longer used clinically because it caused thrombocytopenia and platelet agglutination. It is now used solely to assay those functions in vitro in the diagnosis of conditions such as von Willebrand disease (vWD) and Bernard–Soulier syndrome. Platelet agglutination caused by ristocetin can occur only in the presence of von Willebrand factor multimers, so if ristocetin is added to blood lacking the factor (or its receptor—see below), the platelets will not clump.

Through an unknown mechanism, the antibiotic ristocetin causes von Willebrand factor to bind the platelet receptor glycoprotein Ib (GpIb), so when ristocetin is added to normal blood, it causes agglutination.

Excerpted from Wikipedia’s “ristocetin” article, available under the CC BY-SA 4.0 licence.