Argatroban

Title: Argatroban
CAS Registry Number: 74863-84-6
CAS Name: (2R,4R)-1-[(2S)-5-[(Aminoiminomethyl)amino]-1-oxo-2-[[(1,2,3,4-tetrahydro-3-methyl-8-quinolinyl)sulfonyl]amino]pentyl]-4-methyl-2-piperidinecarboxylic acid
Additional Names: (2R,4R)-4-methyl-1-[N2-(3-methyl-1,2,3,4-tetrahydro-8-quinolinesulfonyl)-L-arginyl]-2-piperidinecarboxylic acid; (2R,4R)-4-methyl-1-[(S)-N2-[[(R,S)-1,2,3,4-tetrahydro-3-methyl-8-quinolinyl]sulfonyl]arginyl]pipecolic acid; argipidine; MQPA
Molecular Formula: C23H36N6O5S
Molecular Weight: 508.63
Percent Composition: C 54.31%, H 7.13%, N 16.52%, O 15.73%, S 6.30%
Literature References: Synthetic thrombin inhibitor. Prepn of argatroban and stereoisomers: R. Kikumoto et al., EP 8746; S. Okamoto et al., US 4258192 (1980, 1981 both to Mitsubishi Chem. Ind.); S. Okamoto et al., Biochem. Biophys. Res. Commun. 101, 440 (1981). Comparison with heparin, q.v., of antithrombotic effect in animals: T. Kumada, Y. Abiko, Thromb. Res. 24, 285 (1981). Stereoselective inhibition of thrombin: R. Kikumoto et al., Biochemistry 23, 85 (1984). Clinical evaluation in hemodialysis: K. Ota et al., Proc. Eur. Dial. Transplant. Assoc. 20, 144 (1983); in disseminated intravascular coagulation: K. Kumon et al., Crit. Care Med. 12, 1039 (1984).
Properties: Crystals from ethanol, mp 188-191°.
Melting point: mp 188-191°
Derivative Type: Monohydrate
CAS Registry Number: 141396-28-3
Manufacturers' Codes: DK-7419; MCI-9038; MD-805; OM-805
Trademarks: Novastan (Tokyo Tanabe); Slonnon (Daiichi)
Properties: Crystals from aq ethanol, mp 176-180°. [a]D27 +76.1° (c = 1 in 0.2N HCl).
Melting point: mp 176-180°
Optical Rotation: [a]D27 +76.1° (c = 1 in 0.2N HCl)
Therap-Cat: Antithrombotic.
Keywords: Antithrombotic.
Arginine Glutamate Aricine Aristolochic Acid Armepavine Arogenic Acid

Argatroban
Argatroban.svg
Systematic (IUPAC) name
(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
Clinical data
Trade names Argatroban
AHFS/Drugs.com monograph
Legal status  ?
Routes intravenous
Pharmacokinetic data
Bioavailability 100% (intravenous)
Protein binding 54%
Metabolism hepatic
Half-life 39 and 51 minutes
Identifiers
CAS number 74863-84-6 YesY
ATC code B01AE03
PubChem CID 440542
DrugBank DB00278
ChemSpider 389444 YesY
UNII OCY3U280Y3 YesY
KEGG C04931 YesY
ChEMBL CHEMBL1166 N
Chemical data
Formula C23H36N6O5S 
Mol. mass 508.635 g/mol
 N (what is this?)  (verify)

Argatroban is an anticoagulant that is a small molecule direct thrombin inhibitor.[1] 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.[2]

Argatroban is given intravenously and drug plasma concentrations reach steady state in 1-3 hours.[3] 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).