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A0487

Sigma-Aldrich

Argatroban monohydrate

≥98% (HPLC)

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Synonym(s):
(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, Argipidine, MQPA
Empirical Formula (Hill Notation):
C23H36N6O5S · H2O
CAS Number:
141396-28-3
Molecular Weight:
526.65
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: ≥20 mg/mL

originator

Baxter

storage temp.

2-8°C

InChI

1S/C23H36N6O5S.H2O/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);1H2/t14-,15?,17?,18-;/m1./s1

InChI key

AIEZTKLTLCMZIA-LINCPPCXSA-N

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General description

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

Application

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).

Biochem/physiol Actions

Argatroban has a high affinity and binds to arginine in thrombin active site resulting in steric hindrance for substrate binding. Argatroban is effective in preventing thrombus formation and favors thrombolysis than unfractionated heparin. It is recommended for acute ischemic stroke treatment.
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.

Features and Benefits

This compound was developed by Baxter. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Arnat Balabiyev et al.
Biomaterials, 277, 121087-121087 (2021-09-04)
Implantation of biomaterials and medical devices in the body triggers the foreign body reaction (FBR) which is characterized by macrophage fusion at the implant surface leading to the formation of foreign body giant cells and the development of the fibrous
Effects of argatroban and heparin on thrombus formation and tissue plasminogen activator-induced thrombolysis in a microvascular thrombosis model
Yamada K, et al.
Thrombosis Research, 109(1), 55-64 (2003)
Photodegradation of aqueous argatroban investigated by LC/MSn: Photoproducts, transformation processes and potential implications
Secretan PH, et al.
Journal of Pharmaceutical and Biomedical Analysis, 131(29387), 223-232 (2016)
Solution-Mediated Phase Transformation of Argatroban: Ternary Phase Diagram, Rate-Determining Step, and Transformation Kinetics
Wang Y, et al.
Industrial & Engineering Chemistry Research, 56(15), 4539-4548 (2017)
Jeremy B Chang et al.
Scientific reports, 6, 29387-29387 (2016-07-22)
A central challenge in designing and administering effective anticoagulants is achieving the proper therapeutic window and dosage for each patient. The Hill coefficient, nH, which measures the steepness of a dose-response relationship, may be a useful gauge of this therapeutic
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