Dexrazoxane (S)-4,4’-(丙烷-1,2-二基)双(哌嗪-2,6-二酮)

CAS 24584-09-6 MFCD00866449

化学结构图

24584-09-6
SMILES: C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1

化学属性

Mol. FormulaC11H16N4O4
Mol. Weight268.27
Melting Point193.0 to 197.0 deg-C
Appearance white solid powder
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical NameDexrazoxane
Synonym (+)-(S)-4,4'-Propylenedi-2,6-piperazinedione (S)-(+)-1,2-Bis(3,5-dioxopiperazin-1-yl)propane Cardioxane ICRF-187 NSC169780 Zinecard 2,6-Piperazinedione, 4,4'-(1-methyl-1,2-ethanediyl)bis-, (+)- ADR 529 ADR529; ADR-529; ADR 529; ICRF-187; ICRF187; ICRF 187; NSC169780; NSC-169780; NSC 169780; Cardioxan; Cardioxane; US brand names: Totect; Zinecard. Foreign brand names: Cardioxane Savene. Dexrazoxane ICRF-187
MDL NumberMFCD00866449
Wiswesser Line NotationT6VMV ENTJ EY1&U1- ET6VMV ENTJ
Beilstein Registry Number5759131
CAS Number24584-09-6
Chemical Name Translation(S)-4,4’-(丙烷-1,2-二基)双(哌嗪-2,6-二酮)
Reaxys-RN6658412
Merck Number8123
PubChem Substance ID160871504
FormulaC11H16N4O4
IUPAC Name(S)-4,4'-(propane-1,2-diyl)bis(piperazine-2,6-dione)
InChIKeyBMKDZUISNHGIBY-ZETCQYMHSA-N
InChIInChI=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
Canonical SMILESC[C@H](N(C1)CC(NC1=O)=O)CN(C2)CC(NC2=O)=O
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分类

  • {SNA} Apoptosis and Cell Cycle, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, D-DIF, DNA Repair Regulators, DNA metabolism, Diversification Ready Pharma-Developed Compounds, Johnson & Johnson, 生物活性小分子, 细胞信号转导和神经科学, 细胞生物学
  • {SNA} Apoptosis and Cell Cycle, Approved Therapeutics/Drug Candidates, Cell Biology, Cell Signaling and Neuroscience, DNA Repair Regulators, DNA metabolism, Johnson & Johnson

产品应用

  • Dexrazoxane is 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. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

安全信息

Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
GHS Symbol
Precautionary statements
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P302+P352+P332+P313+P362+P364
  • P305+P351+P338+P337+P313
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
WGK Germany3
Signal word Warning
Hazard Codes Xi
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
RTECSTL6390000 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 383 mg/kg
TOXIC EFFECTS :
   Gastrointestinal - nausea or vomiting
   Liver - liver function tests impaired
   Blood - leukopenia
REFERENCE :
   CCTRDH Cancer Clinical Trials.  (New York, NY)  V.1-4, 1978-81.
   Volume(issue)/page/year: 4,143,1981

TYPE OF TEST            : LD10 - Lethal Dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CCPHDZ Cancer Chemotherapy and Pharmacology.  (Springer-Verlag New York,
   Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094)  V.1-    1978-
   Volume(issue)/page/year: 38,203,1996

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Mammal - dog
DOSE/DURATION           : 2 gm/kg
TOXIC EFFECTS :
   Behavioral - food intake (animal)
   Gastrointestinal - hypermotility, diarrhea
   Gastrointestinal - nausea or vomiting
REFERENCE :
   CTRRDO Cancer Treatment Reports.  (Washington, DC)  V.60-71, 1976-87.  For
   publisher information,  see JNCIEQ.  Volume(issue)/page/year: 64,1211,1980

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 20 mg/L
REFERENCE :
   INNDDK Investigational New Drugs. The Journal of New Anticancer Agents.
   Kluwer Academic Pub., POB 358, Accord Stn., Hingham, MA 02018)  V.1- 1983- 
   Volume(issue)/page/year: 1,283,1983

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 20 mg/L
REFERENCE :
   INNDDK Investigational New Drugs. The Journal of New Anticancer Agents.
   Kluwer Academic Pub., POB 358, Accord Stn., Hingham, MA 02018)  V.1- 1983- 
   Volume(issue)/page/year: 1,283,1983

Storage condition Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

系列性分类

  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Apoptosis and Cell Cycle - Cell Signaling and Neuroscience
  5. DNA metabolism - Apoptosis and Cell Cycle
  6. DNA Repair Regulators - DNA metabolism
  1. Functional Group 官能团索引
  2. carboxylic acid imide, N-unsubstituted
  1. Medical Research Areas
  2. DNA Damage
  3. Topoisomerase

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