Argatroban

Argatroban is an anticoagulant that is a small molecule direct thrombin inhibitor. In 2000, argatroban was licensed by the Food and Drug Administration (FDA) for prophylaxis or treatment of thrombosis in patients with heparin-induced thrombocytopenia (HIT). In 2002, it was approved for use during percutaneous coronary interventions in patients who have HIT or are at risk for developing it. In 2012, it was approved by the MHRA in the UK for anticoagulation in patients with heparin-induced thrombocytopenia Type II (HIT) who require parenteral antithrombotic therapy.

Argatroban
Clinical data
AHFS/Drugs.comMonograph
License data
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
  • US: ℞-only
Pharmacokinetic data
Bioavailability100% (intravenous)
Protein binding54%
Metabolismhepatic
Elimination half-life39 and 51 minutes
Identifiers
  • (2R,4R)-1-[(2S)-5-(diaminomethylideneamino)-2-
    [[(3R)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]
    sulfonylamino]pentanoyl]-4-methyl-piperidine-2-
    carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.166.378
Chemical and physical data
FormulaC23H36N6O5S
Molar mass508.64 g·mol−1
3D model (JSmol)
SMILES
  • O=C(O)[C@@H]3N(C(=O)C(NS(=O)(=O)c1cccc2c1NCC(C2)C)CCC/N=C(\N)N)CC[C@@H](C)C3
  • 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 N
  • Key:KXNPVXPOPUZYGB-IOVMHBDKSA-N N
 NY (what is this?)  (verify)

Argatroban is given intravenously and drug plasma concentrations reach steady state in 1–3 hours. Argatroban is metabolized in the liver and has a half-life of about 50 minutes. It is monitored by PTT. Because of its hepatic metabolism, it may be used in patients with renal dysfunction. (This is in contrast to lepirudin, a direct thrombin inhibitor that is primarily renally cleared).

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