argatroban   Click here for help

GtoPdb Ligand ID: 6385

Synonyms: DK-7419 | GN-1600 | Gn1600 | MCI-9038 | MD-805
Approved drug
argatroban is an approved drug (FDA (2000))
Compound class: Synthetic organic
Comment: Prescription is by the INN argatroban as there are no brand names. The INN-assigned compound consists of two epimers, and the version we show here matches the structure and stereochemistry in the INN document but does not specify the epimer. One of the epimers is listed on PubChem as CID 152951.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 5
Rotatable bonds 10
Topological polar surface area 188.59
Molecular weight 508.25
XLogP -0.35
No. Lipinski's rules broken 1
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Canonical SMILES NC(=NCCCC(C(=O)N1CCC(CC1C(=O)O)C)NS(=O)(=O)c1cccc2c1NCC(C2)C)N
Isomeric SMILES NC(=NCCC[C@@H](C(=O)N1CC[C@H](C[C@@H]1C(=O)O)C)NS(=O)(=O)c1cccc2c1NCC(C2)C)N
InChI InChI=1S/C23H36N6O5S/c1-14-8-10-29(18(12-14)22(31)32)21(30)17(6-4-9-26-23(24)25)28-35(33,34)19-7-3-5-16-11-15(2)13-27-20(16)19/h3,5,7,14-15,17-18,27-28H,4,6,8-13H2,1-2H3,(H,31,32)(H4,24,25,26)/t14-,15?,17+,18-/m1/s1
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Summary of Clinical Use Click here for help
Argatroban is a thrombin inhibitor for prophylaxis or treatment of thrombosis in patients with, or at risk of, heparin-induced thrombocytopenia (HIT)
Mechanism Of Action and Pharmacodynamic Effects Click here for help
As a thrombin inhibitor, treatment with argatroban disrupts the coagulation cascade and inhibits the formation of blood clots.