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20537-88-6 分子结构
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({2-[(3-aminopropyl)amino]ethyl}sulfanyl)phosphonic acid

ChemBase编号:1014
分子式:C5H15N2O3PS
平均质量:214.222961
单一同位素质量:214.05409998
SMILES和InChIs

SMILES:
S(P(=O)(O)O)CCNCCCN
Canonical SMILES:
NCCCNCCSP(=O)(O)O
InChI:
InChI=1S/C5H15N2O3PS/c6-2-1-3-7-4-5-12-11(8,9)10/h7H,1-6H2,(H2,8,9,10)
InChIKey:
JKOQGQFVAUAYPM-UHFFFAOYSA-N

引用这个纪录

CBID:1014 http://www.chembase.cn/molecule-1014.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
({2-[(3-aminopropyl)amino]ethyl}sulfanyl)phosphonic acid
IUPAC传统名
amifostine
商标名
Ethyol
别名
Aminopropylaminoethyl Thiophosphate
WR-1065
Apaetp
SAPEP
Amifostine Ethiofos
Ethiofos
Gammaphos
amifostine
Amifostine
2-(3-Aminopropyl)aminoethyl phosphorothioate
WR2721
Amifostine
2-[(3-Aminopropyl)-amino]ethanethiol Dihydrogen Phosphate
Phosphorothioic Acid S-[2-[(3-Aminopropyl)amino]ethyl]ester
CSC-296961
Ethyol
CAS号
20537-88-6
MDL号
MFCD00233058
PubChem SID
46505305
160964477
24278231
PubChem CID
2141

数据来源

数据来源

所有数据来源 商品来源 非商品来源

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 2.0575242  质子受体
质子供体 LogD (pH = 5.5) -4.9497204 
LogD (pH = 7.4) -3.7830431  Log P -3.7403424 
摩尔折射率 51.2831 cm3 极化性 20.384901 Å3
极化表面积 95.58 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -1.44  LOG S -1.06 
溶解度 1.87e+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
1000 mg/mL expand 查看数据来源
Water expand 查看数据来源
外观
powder expand 查看数据来源
White Solid expand 查看数据来源
熔点
144-148°C expand 查看数据来源
疏水性(logP)
-1.9 expand 查看数据来源
保存条件
Refrigerator expand 查看数据来源
RTECS编号
TE6491000 expand 查看数据来源
欧盟危险性物质标志
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
22 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
H302 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
纯度
≥97% (TLC) expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
Empirical Formula (Hill Notation)
C5H15N2O3PS expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB01143 external link
Item Information
Drug Groups approved; investigational
Description A phosphorothioate proposed as a radiation-protective agent. It causes splenic vasodilation and may block autonomic ganglia. [PubChem]
Indication For reduction in the cumulative renal toxicity in patients with ovarian cancer (using cisplatin) and moderate to severe xerostomia in patients undergoing post-operative radiation treatment for head and neck cancer.
Pharmacology Amifostine is an organic thiophosphate cytoprotective agent indicated to reduce the cumulative renal toxicity associated with repeated administration of cisplatin in patients with advanced ovarian cancer or non-small cell lung cancer and also to reduce the incidence of moderate to severe xerostomia in patients undergoing post-operative radiation treatment for head and neck cancer. Amifostine is a prodrug that is dephosphorylated by alkaline phosphatase in tissues to a pharmacologically active free thiol metabolite, believed to be responsible for the reduction of the cumulative renal toxicity of cisplatin and for the reduction of the toxic effects of radiation on normal oral tissues. Healthy cells are preferentially protected because amifostine and metabolites are present in healthy cells at 100-fold greater concentrations than in tumour cells.
Toxicity Rat LD50: 826 mg/kg
Affected Organisms
Humans and other mammals
Biotransformation Amifostine is rapidly dephosphorylated by alkaline phosphatase in tissues primarily to the active free thiol metabolite and, subsequently, to a less active disulfide metabolite.
Half Life 8 minutes
Elimination After a 10-second bolus dose of 150 mg/m2 of ETHYOL, renal excretion of the parent drug and its two metabolites was low during the hour following drug administration, averaging 0.69%, 2.64% and 2.22% of the administered dose for the parent, thiol and disulfide, respectively.
References
Santini V, Giles FJ: The potential of amifostine: from cytoprotectant to therapeutic agent. Haematologica. 1999 Nov;84(11):1035-42. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich -  A5922 external link
Application
Amifostine may provide renal protection during PRRT using somatostatin analogs by mitigating radiation damage and reducing the absorbed kidney radiation dose. Amifostine remediates the degenerative effects of radiation on the mineralization capacity of the murine mandible.
Biochem/physiol Actions
Radioprotective agent. Selectively protects normal tissues from the damaging effects of anti-neoplastic radiation therapy. Selectivity is due to preferential uptake by normal tissues and subsequent metabolic activation to 2-(3-aminopropyl)aminoethanethiol.
Toronto Research Chemicals -  A576810 external link
It is a thiophosphate derivative of cysteamine; provides normal cells with selective protection against the toxic effects of cancer chemotherapy and radiation treatment.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Santini V, Giles FJ: The potential of amifostine: from cytoprotectant to therapeutic agent. Haematologica. 1999 Nov;84(11):1035-42. Pubmed
  • Brown, D.Q., et al. Pharmacol. Ther., 39, 159 (1988)
  • Capizzi, R.L., et al.: Cancer, 72, 3495 (1988)
  • Treskes, M., et al.: Cancer Chemother. Pharmacol., 33, 93 (1988)
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专利

专利

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