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Argatroban

Product Name
Argatroban
CAS No.
74863-84-6
Chemical Name
Argatroban
Synonyms
Argatraban;(2R,4R)-4-Methyl-1-[N-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-L-arginyl]-2-piperidinecarboxylic acid;MQP;MQPA;ARG025;MD-805;OM 805;DK-7419;Slonnon;MCI-9038
CBNumber
CB7738830
Molecular Formula
C23H36N6O5S
Formula Weight
508.64
MOL File
74863-84-6.mol
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Argatroban Property

Melting point:
188-1890C
Boiling point:
777.2±70.0 °C(Predicted)
Density 
1.47±0.1 g/cm3(Predicted)
storage temp. 
Keep in dark place,Sealed in dry,2-8°C
solubility 
Soluble in DMSO (up to 50 mg/ml).
pka
10.44±0.40(Predicted)
form 
White to off-white powder.
color 
White
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
InChI
InChI=1S/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-/m1/s1
InChIKey
KXNPVXPOPUZYGB-IOVMHBDKSA-N
SMILES
N1(C(=O)[C@@H](NS(C2C3=C(C=CC=2)CC(C)CN3)(=O)=O)CCCNC(N)=N)CC[C@@H](C)C[C@@H]1C(O)=O
CAS DataBase Reference
74863-84-6(CAS DataBase Reference)
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Safety

Hazardous Substances Data
74863-84-6(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H311Toxic in contact with skin

H331Toxic if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P310Immediately call a POISON CENTER or doctor/physician.

P330Rinse mouth.

P361Remove/Take off immediately all contaminated clothing.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
19639
Product name
Argatroban
Purity
≥95%
Packaging
5mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
19639
Product name
Argatroban
Purity
≥95%
Packaging
10mg
Price
$62
Updated
2024/03/01
Cayman Chemical
Product number
19639
Product name
Argatroban
Purity
≥95%
Packaging
25mg
Price
$142
Updated
2024/03/01
Cayman Chemical
Product number
19639
Product name
Argatroban
Packaging
50mg
Price
$266
Updated
2024/03/01
Tocris
Product number
1637
Product name
Argatroban
Purity
≥99%(HPLC)
Packaging
50
Price
$770
Updated
2021/12/16
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Argatroban Chemical Properties,Usage,Production

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.

Description

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.

Chemical Properties

White to Off-White Crystalline Solid

Originator

Mitsubishi Kasei; Daiichi (Japan)

Uses

anticoagulant;direct thrombine inhibitor

Uses

(2S,4S)-1-(2R)-Argatroban is an isomeric impurity of Argatroban (74863-84-6 #CAS), which is a synthetic thrombin inhibitor. Antithrombotic.

Definition

ChEBI: (2R,4R)-1-[(2S)-5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]-1-oxopentyl]-4-methyl-2-piperidinecarboxylic acid is a peptide.

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);Slonnon.

Therapeutic Function

Anticoagulant

Pharmacokinetics

Argatroban is administered subcutaneously because of the low lipophilicity of the drug. The drug is bound to plasma protein and is metabolized via CYP3A4/5 to the aromatized metabolite and the two hydroxylated metabolites. The M-1 metabolite retains 20 to 30% of the antithrombotic activity. Coadministration of argatroban with inhibitors of CYP3A4 does not appear to produce clinically significant effects. Argatroban is eliminated via biliary secretion into the feces.

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.

Metabolism

The metabolism of argatroban has not yet been fully characterised. The metabolites identified (M-1, M-2, and M-3) are formed by hydroxylation and aromatisation of the 3-methyltetrahydroquinoline ring in the liver. The main metabolite (M1) exerts 40-fold weaker antithrombin effect than argatroban. Metabolites M-1, M-2 and M-3 were detected in the urine, and M-1 was detected in plasma and faeces.
Argatroban is excreted mainly in the faeces, presumably through biliary secretion. Following intravenous infusion of [14C]-argatroban 21.8±5.8% of the dose was excreted in urine and 65.4±7.1% in the faeces.

storage

Store at +4°C

References

1) Kikumoto?et al. (1984),?Selective inhibition of thrombin by (2R,4R)-4-methyl-1-[N2-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-l-arginyl)]-2-piperidinecarboxylic acid; Biochemistry,?23?85 2) Jang?et al. (1990),?Prevention of platelet-rich arterial thrombosis by selective thrombin inhibition; Circulation,?81?219 3) Sugawara?et al. (2009),?Thrombin inhibition by argatroban ameliorates early brain injury and improves neurological outcomes after experimental subarachnoid hemorrhage in rats; Stroke,?40?1530 4) Schulze?et al. (2008),?The thrombin inhibitor Argatroban reduces breast cancer malignancy and metastasis via osteopontin-dependent and osteopontin-independent mechanisms; Breast Cancer Res. Treat.,?112?243

Argatroban Preparation Products And Raw materials

Raw materials

4-METHYL-PYRIDINE-2-CARBOXYLIC ACID 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester 3-Methyl-8-quinolinesulphonyl chloride L(+)-Arginine

Preparation Products

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Argatroban Suppliers

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View Lastest Price from Argatroban manufacturers

BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Argatroban 74863-84-6
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-11-12
Dideu Industries Group Limited
Product
Argatroban 74863-84-6
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons min
Release date
2021-08-04
Zhuozhou Wenxi import and Export Co., Ltd
Product
Argatroban 74863-84-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10

74863-84-6, ArgatrobanRelated Search:

6-Hydroxy-2(1H)-3,4-dihydroquinolinone Methyl acrylate Basic Violet 1 Haloperidol METSULFURON METHYL Methyl salicylate Isoquinoline Kresoxim-methyl Quinclorac Methylparaben 5,6,7,8-TETRAHYDROISOQUINOLINE DROPERIDOL Tribenuron methyl Ethoxyquin Methanol Methyl Argatroban,Argatroban Monohydrate Argatroban Anhydrous

  • Argatroban (Mixture of Diastereomers)
  • Argatroban（mixture of isomers）
  • Argipidine
  • MQP
  • (2R,4R)-4-Methyl-1-[N-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-L-arginyl]-2-piperidinecarboxylic acid
  • ARG025
  • MQPA
  • Argatroban
  • (2R，4R)-1-[5-[(Aminoiminomethyl)amino]-1-oxo-2-[[(1，2，3，4-tetrahydro-3-methyl-8-quinolinyl)sulfonyl]amino]pentyl]-4-methyl-2-piperidinecarboxylic acid
  • (2R)-1-[Nα-(3-Methyl-1,2,3,4-tetrahydroquinoline-8-ylsulfonyl)-L-arginyl]-4α-methylpiperidine-2β-carboxylic acid
  • (2R,4R)-1-[(2S)-5-Guanidino-2-(1,2,3,4-tetrahydro-3-methylquinolin-8-ylsulfonylamino)valeryl]-4-methylpiperidine-2-carboxylic acid
  • MD-805
  • DK-7419
  • MCI-9038
  • MD-805：OM-805：Novastan：Slonnon
  • (2R,4R)-1-((2S)-5-Guanidino-2-(3-Methyl-1,2,3,4-tetrahydroquinoline-8-sulfonaMido)pentanoyl)-4-Methylpiperidine-2-carboxylic acid
  • Novastan
  • OM 805
  • Slonnon
  • 2-Piperidinecarboxylicacid,1-[(2S)-5-[(aMinoiMinoMethyl)aMino]-1-oxo-2-[[(1,2,3,4-tetrahydro-3-Methyl-8-quinolinyl)sulfonyl]aMino]pentyl]-4-Methyl-,(2R,4R)-
  • Argatraban
  • (2R,4R)-1-[(2S)-5-[(Aminoiminomethyl)amino]-1-oxo-2-[[(1,2,3,4-tetrahydro-3-methyl-8-quinolinyl)sulfonyl]amino]pentyl]-
  • Argatroban
  • Ar atroban
  • (2R,4R)-1-((S)-5-Guanidino-2-(3-methyl-1,2,3,4-tetrahydroquinoline-8-sulfonamido)pentanoyl)-4-methylpiperidine-2-carboxylic acid
  • (2S,4S)-1-(2R)-Argatroban
  • (2R,4R)-1-(2S)-Argatroban
  • Argatroban USP/EP/BP
  • Argatroban (10mM in DMSO)
  • Argatroban (MD805
  • TIANFU-CHEM CAS:74863-84-6 Argatroban
  • Agatroban
  • Argatroban (MCI-9038)
  • Agaqu Class
  • 74863-84-6
  • C23H36N6O5S
  • Amines
  • Chiral Reagents
  • Heterocycles
  • Sulfur & Selenium Compounds
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • 74863-84-6