21416-88-6

Basic information

• Product Name: HEPARIN, SODIUM, LOW MOLECULAR WEIGHT
• Synonyms: 2,6-Piperazinedione, 4,4'-(1,2-dimethyl-1,2-ethanediyl)bis-, (R*,S*)-;2,6-Piperazinedione, 4,4'-(1,2-dimethyl-1,2-ethanediyl)bis-, rel-;2,6-Piperazinedione, 4,4'-(1,2-dimethylethylene)di-, meso-;Brn 3981691;meso-2,3-Bis(3,5-dioxopiperazin-1-yl)butane;meso-2,3-Bis(3,5-dioxopiperazine-1-yl)butane
• CAS NO: 21416-88-6
• Molecular Formula: C12H18N4O4
• Molecular Weight: 282.29572
• Mol File: 21416-88-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 526.7°Cat760mmHg
• Flash Point: 272.4°C
• Appearance: /
• Density: 1.308
• Vapor Pressure: 3.48E-11mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: −20°C
• Solubility: DMSO: soluble4mg/mL
• CAS DataBase Reference: HEPARIN, SODIUM, LOW MOLECULAR WEIGHT(CAS DataBase Reference)
• NIST Chemistry Reference: HEPARIN, SODIUM, LOW MOLECULAR WEIGHT(21416-88-6)
• EPA Substance Registry System: HEPARIN, SODIUM, LOW MOLECULAR WEIGHT(21416-88-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: TL6380200
• Hazardous Substances Data: 21416-88-6(Hazardous Substances Data)

Usage

Description

HEPARIN, SODIUM, LOW MOLECULAR WEIGHT is a type of heparin that has been chemically modified to have a lower molecular weight compared to standard heparin. This modification enhances its bioavailability, reduces the risk of side effects, and allows for more precise dosing. It is a highly sulfated glycosaminoglycan that is known for its potent anticoagulant properties, making it a valuable compound in the medical field.

Uses

Used in Pharmaceutical Industry:
HEPARIN, SODIUM, LOW MOLECULAR WEIGHT is used as an anticoagulant for the prevention and treatment of blood clots. Its application is particularly relevant in conditions such as deep vein thrombosis, pulmonary embolism, and during surgical procedures where there is a high risk of clot formation. The low molecular weight of this heparin allows for better control over its anticoagulant effects and reduces the risk of bleeding complications.
Used in Research Applications:
In the field of research, HEPARIN, SODIUM, LOW MOLECULAR WEIGHT is used as a tool to study the role of heparin in various biological processes. It is employed in experiments involving cell culture, molecular biology, and biochemistry to investigate the interactions between heparin and different proteins, enzymes, and other biomolecules. This helps researchers understand the underlying mechanisms of heparin's anticoagulant action and explore its potential therapeutic applications in other areas.
Used in Drug Delivery Systems:
HEPARIN, SODIUM, LOW MOLECULAR WEIGHT is also used in the development of drug delivery systems, particularly for the targeted delivery of therapeutic agents. Its ability to interact with various proteins and cells can be exploited to enhance the specificity and efficiency of drug delivery, potentially improving the treatment of various diseases, including cancer and inflammatory conditions.

Biochem/physiol Actions

ICRF-193 induces a G2 checkpoint that is associated with an ATR-dependent inhibition of polo-like kinase 1 (plk1) activity and a decrease in cyclin B1 phosphorylation. Induces apoptosis in several cell lines including K562 and Molt-4 cells., ICRF-193 is a topoisomerase II inhibitor, more potent against topoisomerase II-β than topoisomerase II-α, and may in addition cause DNA strand breaks.

InChI:InChI=1/C12H18N4O4/c1-7(15-3-9(17)13-10(18)4-15)8(2)16-5-11(19)14-12(20)6-16/h7-8H,3-6H2,1-2H3,(H,13,17,18)(H,14,19,20)/t7-,8+

Downstream Products

• 107903-92-4 2,3-bis(4-morpholinomethyl-3,5-dioxopiperazin-1-yl)butane 

Relevant articles and documents

Inhibition of topoisomerase II by ICRF-193, the meso isomer of 2,3-bis(2,6-dioxopiperazin-4-yl)butane: Critical dependence on 2,3-butanediyl linker absolute configuration

The bis(2,6-dioxopiperazine)s are a structurally and mechanistically unique class of topoisomerase II inhibitors that do not bind DNA and that do not stabilize topoisomerase II-DNA strand passing intermediates ("cleavable complexes"). The most effective topoisomerase II inhibitor in the bis(2,6-dioxopiperazine) series is ICRF-193 (meso or S*, R* isomer), with a meso 2,3-butanediyl linker connecting the dioxopiperazine rings. The two enantiomeric diastereomers, (R,R) and (S,S), of ICRF-193 possessing the two optically active 2,3-butanediyl linkers have been prepared from their respective optically pure 2,4-diaminobutanes via 2,3-diaminobutane-N,N,N′,N′-tetraacetic acid, esterification, and imide formation. Both in vivo and in vitro assays for catalytic inhibition of topoisomerase II were employed to show that the (S,S)-and (R,R)-isomers are almost inactive as topoisomerase II inhibitors. The data indicate that the meso stereochemistry of the alkanediyl linker is crucial for activity and provides additional evidence that the cytotoxicity of the bis(2,6-dioxopiperazine)s is due to their ability to inhibit topoisomerase II. Copyright

Pharmaceutical compositions

Compounds of formula II: wherein n is 0, 1 or 2, R1, R2, R3 and R4 are each separately selected from hydrogen, unsubstituted acyclic aliphatic hydrocarbon groups having a maximum of six carbon atoms and C1 6 alkyl groups substituted by a hydroxy group or a C1 6 alkoxy group, or one of R1 and R2 and one of R3 and R4 is hydrogen and the others are a trimethylene, tetramethylene or pentamethylene bridging group, and R5 as hydrogen or an unsubstituted acyclic aliphatic hydrocarbon group having a maximum of six carbon atoms, but with the provisos that (a) when n is 0 the combinations R1 = R2 = R3 = R4 = R5 = H and R1 = R2 = R3 = R5 = H, R4 = methyl are excluded, and (b) when n is 0, R1, R3 and R5 are each hydrogen, and each of R2 and R4 is other than hydrogen the compound is in other than the mesoor erythroconfiguration, or a salt thereof formed with a physiologically acceptable inorganic or organic acid, are of use in therapy, particularly as cardioprotective agents.