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Argatroban

Product Name
Argatroban
CAS No.
141396-28-3
Chemical Name
Argatroban
Synonyms
GN1600;AG, SAJ;CS-1966;Argatroban API;Acova monohydrate;Argatroban (350 mg);Argatroban 1-hydrate;Argatroban (hydrate);Agatroban monohydrate;Argipidine monohydrate
CBNumber
CB9738829
Molecular Formula
C23H38N6O6S
Formula Weight
526.65
MOL File
141396-28-3.mol
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Argatroban Property

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

WGK Germany 
3
RTECS 
TM6126610
HS Code 
29350090
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A0487
Product name
Argatroban monohydrate
Purity
≥98% (HPLC)
Packaging
5mg
Price
$70.4
Updated
2021/03/22
Sigma-Aldrich
Product number
1042408
Product name
Argatroban monohydrate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
350mg
Price
$1300
Updated
2020/08/18
TCI Chemical
Product number
A2705
Product name
Argatroban Monohydrate
Purity
>99.0%(HPLC)
Packaging
25mg
Price
$228
Updated
2021/03/22
Sigma-Aldrich
Product number
A0487
Product name
Argatroban monohydrate
Purity
≥98% (HPLC)
Packaging
25mg
Price
$285
Updated
2021/03/22
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Argatroban Chemical Properties,Usage,Production

Originator

Acova,SmithKline Beecham

Uses

Anticoagulant.

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

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

Raw materials

Preparation Products

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Argatroban Suppliers

Lianyungang Gabriel Bio-chem Technology Co., Ltd.
Tel
+86 (518) 8548-7361
Fax
+86 (518) 8561-1105
Email
lyggabriel@163.com
Country
China
ProdList
20
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64
Beijing Faith-zone Pharmaceutical Technology Co.,Ltd
Tel
010-87246390
Fax
010-87246290
Email
2848440175@qq.com;2848440175@qq.com
Country
China
ProdList
108
Advantage
55
Kaifute(Tianjin)Chemical Co., Ltd.
Tel
022-58659859
Fax
022-5865 9859
Email
sales@kftchem.com
Country
China
ProdList
299
Advantage
55
Chemvon Biotechnology Co., Ltd
Tel
021-50790412
Fax
+86-21-50790419
Email
info@chemvon.com
Country
China
ProdList
374
Advantage
57
Chembest Research Laboratories Limited
Tel
021-20908456-
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
5948
Advantage
61
JinYan Chemicals(ShangHai) Co.,Ltd.
Tel
13817811078,021-50426030
Fax
86-021-50426522,50426273
Email
sales@jingyan-chemical.com
Country
China
ProdList
10006
Advantage
60
Jia Xing Isenchem Co.,Ltd
Tel
0573-85285100-
Fax
0573-85285100
Email
isenchem@163.com
Country
China
ProdList
9647
Advantage
66
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9844
Advantage
79
TIPR Pharmaceutical Responsible Co., Ltd.
Tel
022-23009155 23006946
Fax
022-27454635
Email
api@cnpha.com
Country
China
ProdList
28
Advantage
68
BOC Sciences
Tel
Email
info@bocsci.com
Country
United States
ProdList
9984
Advantage
65
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View Lastest Price from Argatroban manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Argatroban Monohydrate 141396-28-3
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-26
career henan chemical co
Product
Argatroban 141396-28-3
Price
US $7.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100KG
Release date
2018-12-18

141396-28-3, ArgatrobanRelated Search:


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