149003-01-0 Usage
Description
(S)-4,4'-(1-Methyl-1,2-ethanediyl)bis-2,6-piperazinedione hydrochloride, also known as Dexrazoxane hydrochloride, is a cytoprotective agent derived from the bisdione class of compounds. It is characterized by its ability to chelate iron within cells, which plays a crucial role in its mechanism of action. (S)-4,4'-(1-Methyl-1,2-ethanediyl)bis-2,6-piperazinedione hydrochloride has been synthesized to address specific medical needs, particularly in the context of cancer treatment and its associated side effects.
Uses
Used in Cardiovascular Protection:
(S)-4,4'-(1-Methyl-1,2-ethanediyl)bis-2,6-piperazinedione hydrochloride is used as a cardioprotective agent for reducing the risk and severity of heart damage caused by doxorubicin treatment and similar cancer chemotherapy medications. Heart damage can limit the duration of treatment with doxorubicin, but this compound allows patients to continue treatment for a longer period. It is typically administered after the patient has received several doses of doxorubicin, as its use in the initial doses may reduce the effectiveness of the chemotherapy drug.
Used in the Management of Anthracycline Extravasation:
In the context of anthracycline extravasation, (S)-4,4'-(1-Methyl-1,2-ethanediyl)bis-2,6-piperazinedione hydrochloride is used as a therapeutic agent under the trade name Savene. It works by inhibiting the enzyme topoisomerase II, which is involved in the replication and transcription of DNA. By inhibiting this enzyme, the compound helps to manage the side effects of anthracycline extravasation, a condition where the chemotherapy drug leaks out of the blood vessels and into the surrounding tissue, causing damage and potential complications.
Used in Pharmaceutical Industry:
(S)-4,4'-(1-Methyl-1,2-ethanediyl)bis-2,6-piperazinedione hydrochloride is used as an active pharmaceutical ingredient for the development of medications aimed at reducing cardiotoxicity associated with certain cancer treatments. Its unique ability to chelate iron within cells makes it a valuable compound in the development of new drugs and therapies for cancer patients, particularly those undergoing treatment with doxorubicin or other anthracyclines.
Used in Research and Development:
In the field of research and development, (S)-4,4'-(1-Methyl-1,2-ethanediyl)bis-2,6-piperazinedione hydrochloride serves as a key compound for studying the mechanisms of cardiotoxicity and the potential for developing novel therapies to mitigate these effects. Its use in this context helps to advance our understanding of the complex interactions between chemotherapy drugs, cellular processes, and the development of side effects, ultimately contributing to the development of safer and more effective cancer treatments.
Biological Activity
Dexrazoxane hydrochloride is a topoisomerase II inhibitor and intracellular ion chelator. Bridges and stabilizes an interface between two ATPase promoters to inhibit topoisomerase II activity. Cardioprotective when co-administered with doxorubicin; decreases formation of reactive oxygen species (ROS) and activates the PI3K/Akt survival pathway.
ZINECARD
ZINECARD? (dexrazoxane for injection) is a sterile, pyrogen-free lyophilizate intended for intravenous administration. It is a cardioprotective agent for use in conjunction with doxorubicin.Dexrazoxane, a potent intracellular chelating agent is a derivative of EDTA. Dexrazoxane is a whitish crystalline powder that melts at 191° to 197°C. It is sparingly soluble in water and 0.1 N HCl, slightly soluble in ethanol and methanol, and practically insoluble in nonpolar organic solvents. The pKa is 2.1. Dexrazoxane has an octanol/water partition coefficient of 0.025 and degrades rapidly above a pH of 7.0.ZINECARD is available in 250 mg and 500 mg single use only vials. ZINECARD must be reconstituted with Sterile Water for Injection, USP.Each 250 mg vial contains dexrazoxane hydrochloride equivalent to 250 mg dexrazoxane. Hydrochloric Acid, NF is added for pH adjustment.. When reconstituted as directed with 25 mL of Sterile Water for Injection, USP, each mL contains: 10 mg dexrazoxane. The pH of the resultant solution is 1.0 to 3.0.
Mechanism of action
As a derivative of EDTA, dexrazoxane chelates iron and thus reduces the number of metal ions complexed with anthracycline and, consequently, decrease the formation of superoxide radicals. The exact chelation mechanism is unknown, but it has been postulated that dexrazoxane can be converted into ring-opened form intracellularly and interfere with iron-mediated free radical generation that is in part thought to be responsible for anthryacycline induced cardiomyopathy. It was speculated that dexrazoxane could be used for further investigation to synthesize new antimalarial drugs.
Check Digit Verification of cas no
The CAS Registry Mumber 149003-01-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,9,0,0 and 3 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 149003-01:
(8*1)+(7*4)+(6*9)+(5*0)+(4*0)+(3*3)+(2*0)+(1*1)=100
100 % 10 = 0
So 149003-01-0 is a valid CAS Registry Number.
InChI:InChI=1/C11H16N4O4.ClH/c1-7(15-5-10(18)13-11(19)6-15)2-14-3-8(16)12-9(17)4-14;/h7H,2-6H2,1H3,(H,12,16,17)(H,13,18,19);1H/t7-;/m0./s1
