(2R,4R)-1-[5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid

Base Information

• Chemical Name: (2R,4R)-1-[5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid
• CAS No.: 74863-84-6
• Molecular Formula: C23H36N6O5S
• Molecular Weight: 508.642
• Hs Code.: 2935009090
• European Community (EC) Number: 638-764-8
• Mol file: 74863-84-6.mol

Synonyms:(2R,4R)-1-[5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid;NCGC00164592-01;SCHEMBL4374;AKOS015961851;AKOS026749807;AC-8324;AM84380;C04931;(2R,4R)-4-Methyl-1[Nalpha-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-L-arginyl]-2-piperadinecarboxylic acid

Chemical Property of (2R,4R)-1-[5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid

Chemical Property:

• Appearance/Colour: white to off-white crystalline solid
• Melting Point: 188-189 °C
• Refractive Index: 1.674
• Boiling Point: 801.3 °C at 760 mmHg
• PKA: 10.44±0.40(Predicted)
• Flash Point: 438.4 °C
• PSA: 186.09000
• Density: 1.47 g/cm³
• LogP: 3.65110
• Storage Temp.: Store at +4°C
• Solubility.: Soluble in DMSO (up to 50 mg/ml).
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 508.24678944
• Heavy Atom Count: 35
• Complexity: 887

Purity/Quality:

99% ^*data from raw suppliers

Argatroban ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCN(C(C1)C(=O)O)C(=O)C(CCCN=C(N)N)NS(=O)(=O)C2=CC=CC3=C2NCC(C3)C
• Isomeric SMILES: C[C@@H]1CCN([C@H](C1)C(=O)O)C(=O)C(CCCN=C(N)N)NS(=O)(=O)C2=CC=CC3=C2NCC(C3)C
• Description: Argatroban is a new synthetic antithrombotic agent useful in maintenance anticoagulation them ischemic stroke and disseminated intravascular coagulation. In patients on hemodialysis, argatroban is su enor to heparin, generating a more stable antithrombin effect. Other potential uses include progressing ischemic stroke and disseminated intravascular coagulation. Argatroban is a reversible inhibitor of thrombin (IC50s = 0.01 and 0.09 μM for the free and clot-bound forms, respectively). It is selective for thrombin over factor Xa, trypsin, plasmin, and tissue plasminogen activator (Kis = 0.0045, 53, 0.19, 25.7, and 87.7 μM, respectively). It inhibits thrombin-induced platelet aggregation in washed isolated guinea pig platelets with an IC50 value of 0.077 μM. Argatroban (3.2 mg/kg, s.c.) decreases thrombus formation in a guinea pig model of iron chloride-induced arterial thrombosis. Formulations containing argatroban have been used in the prevention or treatment of thrombosis in patients with heparin-induced thrombocytopenia.
• Uses: anticoagulant;direct thrombine inhibitor (2S,4S)-1-(2R)-Argatroban is an isomeric impurity of Argatroban (74863-84-6 #CAS), which is a synthetic thrombin inhibitor. Antithrombotic.
• Therapeutic Function: Anticoagulant
• Clinical Use: Argatroban has been approved for the prophylaxis and treatment of thrombosis in patients with HIT (79). Argatroban is a peptidomimetic that binds selectively to the catalytic site of thrombin as a univalent competitive DTI. Argatroban is available as a mixture of 21-R and 21-S diastereomers (64:36), with the S-isomer approximately twice as potent as the R-isomer. The drug is a reversible inhibitor of both free thrombin as well as clot-bound thrombin.
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: increased risk of haemorrhage with IV diclofenac and ketorolac - avoid. Antiplatelets and anticoagulants: increased risk of bleeding complications. Heparin: avoid concomitant administration. Urokinase: may increase the risk of bleeding. Thrombolytics: may increase risk of bleeding complications; enhance effect of argatroban.

Technology Process of (2R,4R)-1-[5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid

There total 17 articles about (2R,4R)-1-[5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

→ argatroban (74863-84-6)

Guidance literature:

Reference yield: 93.0%

(2R,4R)-1-[NG-nitro-N2-(3-methyl-8-quinolinesulphonyl)-L-arginyl]-4-methyl-2-piperidine carboxylic acid (74874-10-5) → argatroban (74863-84-6)

Guidance literature:

With hydrogen; 5%-palladium/activated carbon; In methanol; acetic acid; at 85 ℃; for 8h; under 6375.64 Torr; Product distribution / selectivity;

Reference yield: 90.0%

C30H37N7O7S (367952-84-9) → argatroban (74863-84-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; acetic acid; at 20 ℃; for 20h; under 760 Torr;

DOI:10.1016/S0960-894X(01)00351-1

upstream raw materials:

C₃₀H₃₇N₇O₇S

4-methylpiperidin

4-methylpiperidine-1-carboxylic acid tert-butyl ester

8-(chlorosulphonyl)-3-methylquinoline

Refernces

• 1、 -. "METHOD FOR PREPARING ARGATROBAN MONOHYDRATE". Page/Page column 20-21. . Retrieved 2009/11/29.
• 2、 -. "METHOD FOR INHIBITING THROMBOSIS". . . Retrieved 2008/06/13.