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
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
coagulation factor II, thrombin Primary target of this compound Hs Inhibitor Inhibition 7.7 pKi - 1-2
pKi 7.7 (Ki 1.9x10-8 M) [1-2]