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Cardioxane

HCID 6918223
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
1263283-43-7
標準SMILES
C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1.Cl
InChIKey
BIFMNMPSIYHKDN-FJXQXJEOSA-N
分子式
C11H17ClN4O4
平均分子量
304.73 g/mol
単同位体質量
304.0938327

概要

Dexrazoxane Hydrochloride is the hydrochloride salt of a bisdioxopiperazine with iron-chelating, chemoprotective, cardioprotective, and antineoplastic activities. After hydrolysis to an active form that is similar to ethylenediaminetetraacetic acid (EDTA), dexrazoxane chelates iron, limiting the formation of free radical-generating anthracycline-iron complexes, which may minimize anthracycline-iron complex-mediated oxidative damage to cardiac and soft tissues. This agent also inhibits the catalytic activity of topoisomerase II, which may result in tumor cell growth inhibition.

名称と識別子

優先名称
Cardioxane
IUPAC
4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione;hydrochloride
英語名
2,6-Piperazinedione, 4,4′-[(1S)-1-methyl-1,2-ethanediyl]bis-, hydrochloride (1:1)
分子式
C11H16N4O4.ClH
分子量
304.73

名称と別名

Dexrazoxane hydrochloride149003-01-0Dexrazoxane HClCardioxaneTotect1263283-43-7CardioxanSaveneADR-529 hydrochlorideICRF-187 hydrochloride(+)-Razoxane hydrochlorideRazoxane hydrochloride, (S)-
名称をさらに表示
7-DihydroxyflavanoneDexrazoxane monohydrochloride(S)-4,4'-(Propane-1,2-diyl)bis(piperazine-2,6-dione) hydrochloride
2,6-Piperazinedione, 4,4'-((1S)-1-methyl-1,2-ethanediyl)bis-, hydrochloride (1:1)5346058Q7SRazoxane (+)-form hydrochlorideDTXSID601641522,6-Piperazinedione, 4,4'-(1-methyl-1,2-ethanediyl)bis-, hydrochloride, (S)-CHEBI:50224RefChem:56381Dexrazoxane for Injection

データベース識別子

CAS
1263283-43-7、149003-01-0
PubChem CID
6918223
DTXSID
DTXSID60164152
ChEMBL
CHEMBL1200778
UNII
5346058Q7S

物性

構造計算による物性

極性表面積
98.8 Ų
水素結合供与体数
3
水素結合受容体数
6
回転可能結合数
3
重原子数
20
形式電荷
0
複雑度
404

実験および物理化学的性質

Human Drugs · 4 件

Breast Feeding; Lactation; Antineoplastic Agents; Cardioprotectants; Cardiotonic Agents; Enzyme Inhibitors; Topoisomerase II Inhibitors

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

物理化学的性質

貯蔵温度
4 °C, · 4°C, protect from light
溶解性
Soluble in DMSO

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

毒性情報

Treatment · 1 件

There is no known antidote for dexrazoxane. Instances of suspected overdose should be managed with good supportive care until resolution of myelosuppression and related conditions is complete. Management of overdose should include treatment of infections, fluid regulation, and maintenance of nutritional requirements. (L1712)

Exposure RoutesIV administration results in complete bioavailability.
Toxicity Summary · 1 件

The mechanism by which dexrazoxane exerts its cardioprotective activity is not fully understood. Dexrazoxane is a cyclic derivative of EDTA that readily penetrates cell membranes. Results of laboratory studies suggest that dexrazoxane (a prodrug) is converted intracellularly to a ring-opened bidentate chelating agent that chelates to free iron and interferes with iron-mediated free radical generation thought to be responsible, in part, for anthracycline-induced cardiomyopathy. It should be noted that dexrazoxane may also be protective through its inhibitory effect on topoisomerase II.

Signs and SymptomsIntraperitoneal, mouse LD<sub>10</sub> = 500 mg/kg. Intravenous, dog LD<sub>10</sub> = 2 gm/kg.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Dexrazoxane hydrochloride

Ambiguous-DILI-concern

4

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataIntraperitoneal, mouse LD<sub>10</sub> = 500 mg/kg. Intravenous, dog LD<sub>10</sub> = 2 gm/kg.

化学と産業

薬理情報

ATC CodeV03AF02
Metabolism/Metabolites · 1 件

Dexrazoxane is hydrolysed by the enzyme dihydropyrimidine amidohydrolase in the liver and kidney to active metabolites that are capable of binding to metal ions. Route of Elimination: Urinary excretion plays an important role in the elimination of dexrazoxane. Forty-two percent of the 500 mg/m2 dose of dexrazoxane was excreted in the urine. Half Life: 2.5 hours

FDA Pharmacological Classification · 2 件

DEXRAZOXANE FOR INJECTION

Cytoprotective Agent [EPC]

MeSH Pharmacological Classification · 3 件

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.

用途と製造

Uses · 1 件

For reducing the incidence and severity of cardiomyopathy associated with doxorubicin administration in women with metastatic breast cancer who have received a cumulative doxorubicin hydrochloride dose of 300 mg/m^2 and would benefit from continued doxorubicin therapy. Also approved for the treatment of extravasation from intravenous anthracyclines.

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安全データ

危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302