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74863-84-6

(2R,4R)-4-Methyl-1-[Nalpha-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-L-arginyl]-2-piperidinecarboxylic acid

CAS: 74863-84-6;141396-28-3;121785-71-5

Molecular Formula: C23H36N6O5S

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74863-84-6 - Names and Identifiers

Name (2R,4R)-4-Methyl-1-[Nalpha-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-L-arginyl]-2-piperidinecarboxylic acid
Synonyms 21R-
GN1600
Argatroban
Agaquban 21R
21R-Argatroban
Argatroban Monohydrate
(2r,4r)-4-methyl-1-[n-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-l-arginyl]-2-piperidinecarboxylic acid
(2R,4R)-4-Methyl-1-[Nalpha-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-L-arginyl]-2-piperidinecarboxylic acid
(2R,4R)-1-[N2-3-(methyl-1,2,3,4-tetrahydro-8-quinolinesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid monohydrate
(2R,4R)-1-[(2S)-5-guanidino-2-[[(3R)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonylamino]pentanoyl]-4-methyl-pipecolinic acid
(2R,4R)-1-{N~5~-(diaminomethylidene)-N~2~-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonyl]ornithyl}-4-methylpiperidine-2-carboxylic acid
(2R,4R)-1-{N~5~-(diaminomethylidene)-N~2~-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonyl]-L-ornithyl}-4-methylpiperidine-2-carboxylic acid
(2R,4R)-1-[N~5~-(diaminomethylidene)-N~2~-{[(3R)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonyl}-L-ornithyl]-4-methylpiperidine-2-carboxylic acid
(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
(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
(2R,4R)-1-[(2S)-5-[(AMinoiMinoMethyl)aMino]-1-oxo-2-[[[(3R)-1,2,3,4-tetrahydro-3-Methyl-8-quinolinyl]sulfonyl]aMino]pentyl]-4-Methyl-2-piperidinecarboxylic Acid
(2R,4R)-1-[(2S)-5-[bis(azanyl)methylideneamino]-2-[[(3R)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonylamino]pentanoyl]-4-methyl-piperidine-2-carboxylic acid
2-Piperidinecarboxylicacid,1-[(2S)-5-[(aminoiminomethyl)amino]-1-oxo-2-[[[(3R)-1,2,3,4-tetrahydro-3-methyl-8-quinolinyl]sulfonyl]amino]pentyl]-4-methyl-,(2R,4R)-
2-Piperidinecarboxylic acid, 1-(5-((aminoiminomethyl)amino)-1-oxo-2-(((1,2,3,4-tetrahydro-3-methyl-8-quinolinyl)sulfonyl)amino)pentyl)-4-methyl-, (2R-(1(S*(R*)),2alpha,4beta))-
CAS 74863-84-6
141396-28-3
121785-71-5
InChI InChI=1/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-/m0/s1

74863-84-6 - Physico-chemical Properties

Molecular FormulaC23H36N6O5S
Molar Mass508.63
Density1.47±0.1 g/cm3(Predicted)
Melting Point-41.5 ℃
Boling Point777.2±70.0 °C(Predicted)
AppearanceWhite to white-like powder
pKa10.44±0.40(Predicted)
Storage Condition2-8℃
Refractive Index1.674
MDLMFCD00895735

74863-84-6 - Nature

Open Data Verified Data

crystallized from ethanol, melting point 18 8-191 °c.

Last Update：2024-01-02 23:10:35

74863-84-6 - Preparation Method

Open Data Verified Data

Nitro-N-tert-butoxycarbonyl arginine and 4-methyl -2-pyridine carboxylic acid ethyl ester reaction, the obtained compound, and then 3-methyl -8-quinoline sulfonyl chloride acylation, the compound is obtained by hydrolysis to free carboxylic acid, followed by catalytic hydrogenation on palladium carbon to obtain argatroban.

Last Update：2025-06-10 22:55:16

74863-84-6 - Application

Open Data Verified Data

developed by Japan first pharmaceutical company and Japan Mitsubishi Corporation, launched in 1990. Antithrombotic drugs. Argatroban is a thrombin inhibitor with strong selective inhibition of thrombin. Inhibition of platelet aggregation caused by thrombin, the inhibition of fibrin is weak, there is a role in the promotion of fibrinolysis. For chronic arterial occlusive disease.

Last Update：2025-08-19 16:24:40

74863-84-6 - Reference Information

anticoagulant Argatroban is a synthetic anticoagulant and a reversible competitive thrombin inhibitor. It has a strong selective inhibitory effect on thrombin and inhibits platelet aggregation caused by thrombin. The inhibitory effect on fibrinase is weak. In vitro, thrombi generated by various thrombotic models is inhibited. In the experimental model, it has been proved that this drug is significantly better than heparin in preventing coronary artery thrombosis, and can competitively inhibit thrombin-induced platelet activation and aggregation. Unlike heparin, argatroban does not cause thrombocytopenia and does not further prolong the bleeding time after aspirin is added. Preliminary studies have confirmed that the combination of this drug and aspirin is an effective combination to prevent coronary artery thrombosis. Agatroban is effective for unstable angina pectoris.
The anticoagulant effect of this product does not require the cooperation of antithrombin III. It can be distributed quickly in tissues, mainly in liver, kidney and digestive tract. PBP is 35% ~ 60%. Metabolites are mainly compounds with aromatic rings and hydroxyl groups, which are excreted about 50% from urine and feces 24h after administration, and most of them are excreted 48h after administration.
clinical application argatroban is the first antithrombotic drug developed and synthesized by Mitsubishi (Mitsubishi) Institute of Chemistry in Japan. It was first applied in the clinical treatment of peripheral arterial occlusive disease, and then began to be used in the treatment of acute cerebral thrombosis, as well as in the adjuvant treatment of thrombolysis in myocardial infarction, and for anticoagulation in patients with antithrombin (AT) deficiency during hemodialysis. As the world's first selective antithrombin agent, Argatroban was launched in Japan in February 1990. The clinical application so far has verified its therapeutic effect on hemodialysis in patients with acute cerebral thrombosis, chronic arterial occlusive disease and antithrombin III(ATIII) deficiency. In addition, as a drug for the prevention and treatment of heparin-induced thromboembolism, the U.S. Food and Drug Administration (FDA) approved in 2000 the injectable antithrombotic small molecule drug argatroban (argatroban,Novastan) of SmithKline Beecham and Texas Bitechnology for the treatment and prevention of thrombosis and heparin-induced immune disease-thrombocytopenia (HIT), and for the treatment of patients requiring percutaneous coronary intervention (PCI).
The results of the multi-center phase II clinical trial announced at the 28th International Stroke Conference of the American Stroke Society on March 5, 2003 showed that argatroban has significant efficacy and high safety in the treatment of acute ischemic stroke. As a treatment for acute cerebral thrombosis and chronic arterial occlusive disease, Argatroban was launched in South Korea in 2001.
in December 2002, Mitsubishi pharmaceutical company officially listed the selective antithrombin argatroban (Argatroban,Novastan) for the treatment of chronic arterial occlusive disease in China.
Last Update：2024-04-09 21:21:28
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