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Argatroban

CAS No.
141396-28-3
Chemical Name:
Argatroban
Synonyms
Argatroban Monohydrate;(2r,4r)-4-methyl-1-[n-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-l-arginyl]-2-piperidinecarboxylic acid;GN1600;AG, SAJ;CS-1966;US-DMF:035491;Argatroban API;Acova monohydrate;Argatroban (350 mg);API Cas:141396-28-3
CBNumber:
CB9738829
Molecular Formula:
C23H38N6O6S
Molecular Weight:
526.65
MDL Number:
MFCD00895735
MOL File:
141396-28-3.mol
MSDS File:
SDS
Last updated:2023-08-11 15:49:39

Argatroban Properties

Melting point 176-180°
alpha D27 +76.1° (c = 1 in 0.2N HCl)
storage temp. 2-8°C
solubility DMSO: ≥20mg/mL
form Solid
color white to off-white
Merck 14,779
CAS DataBase Reference 141396-28-3(CAS DataBase Reference)
FDA UNII IY90U61Z3S

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS02
Signal word  Warning
Hazard statements  H223+H229
WGK Germany  3
RTECS  TM6126610
HS Code  29350090
Toxicity mouse,LD50,intraperitoneal,475mg/kg (475mg/kg),LUNGS, THORAX, OR RESPIRATION: DYSPNEABLOOD: NORMOCYTIC ANEMIABEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14(Suppl,

Argatroban price More Price(35)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A0487 Argatroban monohydrate ≥98% (HPLC) 141396-28-3 5mg $84.1 2024-03-01 Buy
Sigma-Aldrich 1042408 Argatroban monohydrate United States Pharmacopeia (USP) Reference Standard 141396-28-3 350mg $1560 2024-03-01 Buy
TCI Chemical A2705 Argatroban Monohydrate >99.0%(HPLC) 141396-28-3 25mg $188 2024-03-01 Buy
Sigma-Aldrich A0487 Argatroban monohydrate ≥98% (HPLC) 141396-28-3 25mg $340 2024-03-01 Buy
TRC A769005 Argatroban monohydrate 141396-28-3 25mg $90 2021-12-16 Buy
Product number Packaging Price Buy
A0487 5mg $84.1 Buy
1042408 350mg $1560 Buy
A2705 25mg $188 Buy
A0487 25mg $340 Buy
A769005 25mg $90 Buy

Argatroban Chemical Properties,Uses,Production

Originator

Acova,SmithKline Beecham

Uses

Anticoagulant.

Uses

Argatroban monohydrate has been used as a thrombin-selective inhibitor in the thrombin assay of platelet poor plasma samples. It may be used as a standard in gradient reversed-phase liquid chromatography coupled with high-resolution multistage mass spectrometry (LC/HR-MSn) for photoproducts fragmentation analysis and as a thrombin inhibitor competitive assay with fullerene-based C60 nanoparticle (NPs).

Manufacturing Process

To a stirred solution of 28.3 g of NG-nitro-N2-(tert-butoxycarbonyl)-L-arginine in 450 ml of dry tetrahydrofuran were added in turn 9.0 g of triethylamine and 12.2 g of isobutyl chloroformate while keeping the temperature at -20°C. After 10 minutes, to this was added 15.2 g of ethyl 4-methyl-2- piperidinecarboxylate and the mixture was stirred for 10 minutes at -20°C. At the end of this period, the reaction mixture was warmed to room temperature. The solvent was evaporated and the residue taken up in 400 ml of ethyl acetate, and washed successively with 200 ml of water, 100 ml of 5% sodium bicarbonate solution, 100 ml of 10% citric acid solution and 200 ml of water. The ethyl acetate solution was dried over anhydrous sodium sulfate. The solution was evaporated to give 31.5 g (75 %) of ethyl 1-[NG-nitro-N2- (tert-butoxycarbonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylate in the form of a syrup.
To a stirred solution of 30 g of ethyl 1-[NG-nitro-N2-(tert-butoxycarbonyl)-Larginyl]- 4-methyl-2-piperidinecarboxylate in 50 ml of ethyl acetate was added 80 ml of 10% dry HCl-ethyl acetate at 0°C. After 3 hours, to this solution was added 200 ml of dry ethyl ether to precipitate a viscous oily product. This was filtered and washed with dry ethyl ether to give ethyl 1-[NG-nitro-L-arginyl]-4- methyl-2-piperidinecarboxylate hydrochloride as an amorphous solid.
To a stirred solution of ethyl 1-(NG-nitro-L-arginyl)-4-methyl-2- piperidinecarboxylate hydrochloride in 200 ml of chloroform were added in turn 18.5 g of triethylamine, and 14.7 g of 3-methyl-8-quinolinesulfonyl chloride at 5°C, and stirring was continued for 3 hours at room temperature. At the end of this period, the solution was washed twice with 50 ml of water. The chloroform solution was dried over anhydrous sodium sulfate. Upon evaporation of the solvent, the residue was chromatographed on 50 g of silica gel packed in chloroform, washed with chloroform and eluted with 3% methanol-chloroform. The fraction eluted from 3% methanol-chloroform was evaporated to give 32.1 g (91%) of ethyl 1-[NG-nitro-N2-(3-methyl-8- quinolinesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylate in the form of an amorphous solid.
A solution of 30 g the above product in 100 ml of ethanol and 100 ml of 1 N sodium hydroxide solution was stirred for 24 hrs at room temperature. At the end of this period, the solution was neutralized with 1 N hydrochloric acid and then concentrated to 70 ml. The solution was adjusted to pH=11 with 1 N sodium hydroxide solution, washed three times with 100 ml of ethyl acetate, acidified with 1 N hydrochloric acid and then extracted three times with 100 ml of chloroform. The combined chloroform solution was dried over anhydrous sodium sulfate and evaporated to give 28.0 g (97%) of 1-[NG-nitro-N2-(3- methyl-8-quinolinesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid as an amorphous solid. IR (KBr): 3,300, 1,720, 1,630 cm-1.
To a solution of 3.00 g of 1-[NG-nitro-N2-(3-methyl-8-quinolinesulfonyl)-Larginyl]- 4-methyl-2-piperidinecarboxylic acid in 50 ml of ethanol was added 0.5 g of palladium black and then the mixture was shaken under 10 kg/cm2 H2 pressure at 100°C for 8 hrs. At the end of this period, the ethanol solution was filtered to remove the catalyst and evaporated to give 2.50 g (90%) of 1- [N2-(3-methyl-1,2,3,4-tetrahydro-8-quinolinesulfonyl)-L-arginyl]-4-methyl-2- piperidinecarboxylic acid as an amorphous solid. IR (KBr): 3,400, 1,620, 1,460, 1,380 cm-1.

brand name

Novastan (Mitsubishi Chemical Corporation, Japan).

Therapeutic Function

Anticoagulant

General Description

Argatroban anticoagulant is synthesized from L-arginine and photodegrades under light exposure.

Biochem/physiol Actions

Argatroban is a potent, seletive, univalent direct inhibitor of thrombin. It directly inhibits thrombin by binding only to its active site (thus univalent) as compared to Bivalent DTIs (hirudin and analogs) which bind both to the active site and exosite 1.

Enzyme inhibitor

This anticoagulant (FW = 508.64 g/mol; CAS 74863-84-6), also named (2R,4R) -4-methyl-1-N2-[ (3-methyl-1,2,3,4-tetrahydro-8-quinolilyl) sulfon- yl]-L-arginyl-2-piperidine carboxylic acid, Novastan?, and MD-805, is a direct thrombin inhibitor (1-11) that is an effective treatment for heparin- induced thrombocytopenia (HIT), an immunoglobulin-mediated adverse drug reaction characterized by platelet activation, thrombocytopenia, and a high risk of thrombotic complications among patients who are receiving or have recently received heparin. HIT is an autoimmune-like disorder, with the target antigen a multimolecular complex of the “self” protein, Platelet Factor-4, and heparin. Continued use of heparin is ill-advised and dangerous. Argatroban is also indicated for the treatment of heparin- induced thrombocytopenia and thrombosis syndrome (HITTS), an immune- mediated response to the administration of heparin that results in life- threatening thrombosis. Argatroban is one of four FDA-approved parenteral direct thrombin inhibitors, the others being lepirudin, desirudin, and bivalirudin. Argatroban is metabolized in the liver (t1/2 = ~50 min). Other DTI’s include recombinant hirudins, bivalirudin, and ximelagatran, either alone or in combination with melagatran. Argatroban is a significantly weaker inhibitor of trypsin, K = 4.3 μM, plasmin (K = ii 800 μM), coagulation factor Xa, and plasma kallikrein (Ki = 2 mM). Commercial sources often supply a mixture of 21 (R) and 21 (S) Diastereoisomers. The latter is more potent.

Argatroban Preparation Products And Raw materials

Global( 281)Suppliers
Supplier Tel Email Country ProdList Advantage
Henan Bao Enluo International TradeCo.,LTD
+86-17331933971 +86-17331933971 deasea125996@gmail.com China 2504 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497 sales01@cooperate-pharm.com CHINA 1811 55
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+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
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+86-21-33585366 - 03@ sales03@shyrchem.com CHINA 738 60
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BOC Sciences
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+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58
Shanghai Yingrui Biopharma Co.,Ltd
21-33585366 export01@shyrchem.com CHINA 1320 58

View Lastest Price from Argatroban manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Argatroban pictures 2023-08-12 Argatroban
141396-28-3
US $80.00 / kg 1kg 99% 1000tons Henan Bao Enluo International TradeCo.,LTD
Argatroban pictures 2023-06-26 Argatroban
141396-28-3
US $200.00 / kg 1kg 99% 1000kg/Months Hebei Mingeng Biotechnology Co., Ltd
Argatroban pictures 2023-04-20 Argatroban
141396-28-3
US $50.00 / kg 1kg 99% 50 tons Hebei Duling International Trade Co. LTD
  • Argatroban pictures
  • Argatroban
    141396-28-3
  • US $80.00 / kg
  • 99%
  • Henan Bao Enluo International TradeCo.,LTD
  • Argatroban pictures
  • Argatroban
    141396-28-3
  • US $200.00 / kg
  • 99%
  • Hebei Mingeng Biotechnology Co., Ltd
  • Argatroban pictures
  • Argatroban
    141396-28-3
  • US $50.00 / kg
  • 99%
  • Hebei Duling International Trade Co. LTD
Argatroban (hydrate) Argatroban (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 Argatroban (350 mg) (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 hydrate (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 GN1600 (2R,4R)-1-[N2-3-(methyl-1,2,3,4-tetrahydro-8-quinolinesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid monohydrate Argatroban API (2R,4R)-4-Methyl-1-[Nalpha-[(3-Methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-L-arginyl]-2-piperidinecarboxylic acid Argatroban 1-hydrate AG, SAJ Agatroban monohydrate CS-1966 Acova monohydrate Argipidine monohydrate ARGIPIDINE MONOHYDRATE; ACOVA MONOHYDRATE (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 Argatroban Monohydrate> Argatroban hydrate (MD805 (2R,4R)-4-Methyl-1-[Nalpha-[(3-methyl-1,2,3,4-tetrahydro-8-q... US-DMF:035491 (2R,4R)-1-[(2S)-5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid Argatroban (1042408) (2r,4r)-4-methyl-1-[n-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-l-arginyl]-2-piperidinecarboxylic acid Argatroban Monohydrate Benzenesulfonicacid,8-(acetylamino)-,hydrazide (2R,4R)-1-((2S)-5-Guanidino-2-(3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonamido)pentanoyl)-4-methylpiperidine-2-carboxylic acid hydrate API Cas:141396-28-3 (2R,4R)-1-((2S)-5-Guanidino-2-(3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonamido)pentanoyl)-4-methylpiperidine-2-carboxylic acid hydrate? (Argatroban Impurity) 141396-28-3 C23H36N6O5SH2O