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24584-09-6 分子结构
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4-[(2S)-1-(3,5-dioxopiperazin-1-yl)propan-2-yl]piperazine-2,6-dione

ChemBase编号:264
分子式:C11H16N4O4
平均质量:268.26914
单一同位素质量:268.11715501
SMILES和InChIs

SMILES:
O=C1NC(=O)CN([C@H](CN2CC(=O)NC(=O)C2)C)C1
Canonical SMILES:
O=C1NC(=O)CN(C1)C[C@@H](N1CC(=O)NC(=O)C1)C
InChI:
InChI=1S/C11H16N4O4/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)/t7-/m0/s1
InChIKey:
BMKDZUISNHGIBY-ZETCQYMHSA-N

引用这个纪录

CBID:264 http://www.chembase.cn/molecule-264.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
4-[(2S)-1-(3,5-dioxopiperazin-1-yl)propan-2-yl]piperazine-2,6-dione
4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione
IUPAC传统名
4-[(2S)-1-(3,5-dioxopiperazin-1-yl)propan-2-yl]piperazine-2,6-dione
dexrazoxane
商标名
Cardioxane
Dyzoxane
Eucardion
Razoxane
Razoxin
Tepirone
Troxozone
Zinecard
别名
Dexrazoxano [INN-Spanish]
Dexrazoxanum [INN-Latin]
Dextrorazoxane
Desrazoxane
Razoxana [INN-Spanish]
Razoxanum [INN-Latin]
Icrf-187
Dexrazoxane
(+)-(S)-4,4′-Propylenedi-2,6-piperazinedione
(S)-(+)-1,2-Bis(3,5-dioxopiperazin-1-yl)propane
Cardioxane
NSC169780
Zinecard
Dexrazoxane
(S)-4,4'-(Propane-1,2-diyl)bis(piperazine-2,6-dione)
CAS号
24584-09-6
MDL号
MFCD00866449
PubChem SID
46505982
160963727
PubChem CID
71384

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 11.198792  质子受体
质子供体 LogD (pH = 5.5) -2.6580358 
LogD (pH = 7.4) -2.6527913  Log P -2.652655 
摩尔折射率 64.2532 cm3 极化性 25.298058 Å3
极化表面积 98.82 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -1.05  LOG S -1.41 
溶解度 1.04e+01 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
DMSO: >20 mg/mL expand 查看数据来源
Sparingly soluble expand 查看数据来源
外观
white to off-white powder expand 查看数据来源
疏水性(logP)
-2.6 expand 查看数据来源
欧盟危险性物质标志
刺激性(Irritant) 刺激性(Irritant) (Xi) expand 查看数据来源
联合国危险货物编号
2811 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
联合国危险货物等级
6.1 expand 查看数据来源
联合国危险货物包装类别(PG)
3 expand 查看数据来源
危险公开号
36/37/38 expand 查看数据来源
安全公开号
26-36 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H315-H319-H335 expand 查看数据来源
GHS警示性声明
P261-P305 + P351 + P338 expand 查看数据来源
RID/ADR
UN 2811 6.1/PG 3 expand 查看数据来源
保存温度
room temp expand 查看数据来源
纯度
≥95% (HPLC) expand 查看数据来源
95+% expand 查看数据来源
97% expand 查看数据来源
Empirical Formula (Hill Notation)
C11H16N4O4 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Sigma Aldrich Sigma Aldrich
DrugBank -  DB00380 external link
Item Information
Drug Groups approved
Description An antimitotic agent with immunosuppressive properties. Dexrazoxane, the (+)-enantiomorph of razoxane, provides cardioprotection against anthracycline toxicity. It appears to inhibit formation of a toxic iron-anthracycline complex. [PubChem]
The Food and Drug Administration has designated dexrazoxane as an orphan drug for use in the prevention or reduction in the incidence and severity of anthracycline-induced cardiomyopathy.
Indication 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.
Pharmacology Dexrazoxane is a cardioprotective agent for use in conjunction with doxorubicin indicated for reducing the incidence and severity of cardiomyopathy associated with doxorubicin administration in women with metastatic breast cancer who have received a cumulative doxorubicin dose. Patients receiving anthracycline-derivative antineoplastic agents may experience three types of cardiotoxicity: acute transient type; chronic, subacute type (related to cumulative dose and has a more indolent onset later on); and a late-onset type that manifests years after therapy, mainly in patients that have been exposed to the drug as a child. Although the exact mechanism of anthracycline-induced cardiotoxicity is not known, it has shown to exert a variety of actions that may result in the development of cardiotoxicity. In animals, anthracyclines cause a selective inhibition of cardiac muscle gene expression for α-actin, troponin, myosin light-chain 2, and the M isoform of creatine kinase. This may lead to myofibrillar loss associated with anthracycline-induced cardiotoxicity. Anthracyclines may also cause myocyte damage via calcium overload, altered myocardial adrenergic function, release of vasoactive amines, and proinflammatory cytokines. Furthermore, it has been suggested that the main cause of anthracycline-induced cardiotoxicity is associated with free-radical damage to DNA. The drugs intercalate DNA, chelate metal ions to produce drug-metal complexes, and generate superoxide radicals via oxidation-reduction reactions. Anthracyclines also contain a quinone structure that can undergo reduction via NADPH-dependent reactions to produce a semiquinone free radical that initiates a cascade of superoxide and hydroxide radical generation. Chelation of metal ions, particularly iron, by anthracyclines results in an anthracycline-metal complex that catalyzes the generation of reactive oxygen free radicals. This complex is a powerful oxidant that can initiate lipid peroxidation in the absence of oxygen free radicals. The toxicity induced by antrhacyclines may be exacerbated in cardiac cells, as these cells do not possess sufficient amounts of certain enzymes (e.g., superoxide dismutase, catalase, glutathione peroxidase) involved in detoxifying free radicals and protecting the cells from subsequent damage.
Toxicity Intraperitoneal, mouse LD10 = 500 mg/kg. Intravenous, dog LD10 = 2 gm/kg.
Affected Organisms
Humans and other mammals
Biotransformation Dexrazoxane is hydrolysed by the enzyme dihydropyrimidine amidohydrolase in the liver and kidney to active metabolites that are capable of binding to metal ions.
Absorption IV administration results in complete bioavailability.
Half Life 2.5 hours
Protein Binding Very low (< 2%)
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.
Distribution * 9 to 22.6 L/m^2
Clearance * 7.88 L/h/m2 [dose of 50 mg/m2 Doxorubicin and 500 mg/m2 Dexrazoxane]
* 6.25 L/h/m2 [dose of 60 mg/m2 Doxorubicin and 600 mg/m2 Dexrazoxane]
References
Hasinoff BB, Herman EH: Dexrazoxane: how it works in cardiac and tumor cells. Is it a prodrug or is it a drug? Cardiovasc Toxicol. 2007;7(2):140-4. [Pubmed]
Hasinoff BB: The use of dexrazoxane for the prevention of anthracycline extravasation injury. Expert Opin Investig Drugs. 2008 Feb;17(2):217-23. [Pubmed]
Kik K, Szmigiero L: [Dexrazoxane (ICRF-187)--a cardioprotectant and modulator of action of some anticancer drugs] Postepy Hig Med Dosw (Online). 2006;60:584-90. [Pubmed]
Weiss G, Loyevsky M, Gordeuk VR: Dexrazoxane (ICRF-187). Gen Pharmacol. 1999 Jan;32(1):155-8. [Pubmed]
Langer SW: Dexrazoxane for anthracycline extravasation. Expert Rev Anticancer Ther. 2007 Aug;7(8):1081-8. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich -  D1446 external link
Biochem/physiol Actions
Dexrazoxane is a cardioprotective compound against anthracyclines. It functions by inhibiting topoisomerase II without inducing DNA strand breaks. Dexrazoxane is a + enantiomer of razoxane.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Hasinoff BB, Herman EH: Dexrazoxane: how it works in cardiac and tumor cells. Is it a prodrug or is it a drug? Cardiovasc Toxicol. 2007;7(2):140-4. Pubmed
  • Hasinoff BB: The use of dexrazoxane for the prevention of anthracycline extravasation injury. Expert Opin Investig Drugs. 2008 Feb;17(2):217-23. Pubmed
  • Kik K, Szmigiero L: [Dexrazoxane (ICRF-187)--a cardioprotectant and modulator of action of some anticancer drugs] Postepy Hig Med Dosw (Online). 2006;60:584-90. Pubmed
  • Langer SW: Dexrazoxane for anthracycline extravasation. Expert Rev Anticancer Ther. 2007 Aug;7(8):1081-8. Pubmed
  • Weiss G, Loyevsky M, Gordeuk VR: Dexrazoxane (ICRF-187). Gen Pharmacol. 1999 Jan;32(1):155-8. Pubmed
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