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52-24-4 分子结构
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tris(aziridin-1-yl)-λ5-phosphanethione

ChemBase编号:4140
分子式:C6H12N3PS
平均质量:189.218341
单一同位素质量:189.04895503
SMILES和InChIs

SMILES:
P(=S)(N1CC1)(N1CC1)N1CC1
Canonical SMILES:
S=P(N1CC1)(N1CC1)N1CC1
InChI:
InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2
InChIKey:
FOCVUCIESVLUNU-UHFFFAOYSA-N

引用这个纪录

CBID:4140 http://www.chembase.cn/molecule-4140.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
tris(aziridin-1-yl)-λ5-phosphanethione
tris(aziridin-1-yl)-$l^{5}-phosphanethione
IUPAC传统名
thiophosphamide
ThioTEPA
别名
1,1',1''-Phosphorothioyltriaziridine
N,N′,N″-Triethylenethiophosphoramide
Thio-Tep
Thiofozil
Thiotef
Tio-tef
Tiofozil
Tris(aziridinyl)phosphine sulfide
Thio-TEPA
Thiotepa
Thioplex
Tiofosyl
Tiofosfamid
1,1’,1’’-Phosphinothioylidynetrisaziridine
Tris(1-aziridinyl)phosphine Sulfide
AI 3-24916
CBC 806495
Girostan
N,N’,N’’-Triethylenethiophosphoramide
Oncotepa
Oncothio-tepa
Oncotiotepa
Phosphorothioic Acid Triethylenetriamide
Tespamin
Tespamine
Tris(aziridinyl)phosphine-thioxide
Thio-TEPA
Triethylenethiophosphoramide
CAS号
52-24-4
EC号
200-135-7
MDL号
MFCD00145452
PubChem SID
24900346
160967572
PubChem CID
5453

理论计算性质

理论计算性质

JChem ALOGPS 2.1
质子受体 质子供体
LogD (pH = 5.5) -1.0273812  LogD (pH = 7.4) -1.0273805 
Log P -1.0273805  摩尔折射率 50.7222 cm3
极化性 20.823643 Å3 极化表面积 9.03 Å2
可自由旋转的化学键 里宾斯基五规则 true 
Log P 0.17  LOG S -1.31 
溶解度 9.27e+00 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
Benzene expand 查看数据来源
外观
solid expand 查看数据来源
White Solid expand 查看数据来源
熔点
52-54°C expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Refrigerator expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
RTECS编号
SZ2975000 expand 查看数据来源
欧盟危险性物质标志
剧毒(Highly toxic) 剧毒(Highly toxic) (T+) 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
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
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)
2 expand 查看数据来源
危险公开号
45-46-28 expand 查看数据来源
安全公开号
53-22-26-36/37/39-45 expand 查看数据来源
TSCA收录
false expand 查看数据来源
GHS危险品标识
GHS06 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H300-H350 expand 查看数据来源
GHS警示性声明
P201-P264-P301 + P310-P308 + P313 expand 查看数据来源
个人保护装置
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand 查看数据来源
RID/ADR
UN 2811 6.1/PG 2 expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
纯度
98% expand 查看数据来源
成盐信息
Free Base 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)
C6H12N3PS expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB04572 external link
Item Information
Drug Groups approved
Description N,N'N'-triethylenethiophosphoramide (ThioTEPA) is a cancer chemotherapeutic member of the alkylating agent group, now in use for over 50 years. It is a stable derivative of N,N',N''- triethylenephosphoramide (TEPA). It is mostly used to treat breast cancer, ovarian cancer and bladder cancer. It is also used as conditioning for Bone marrow transplantation. Its main toxicity is myelosuppression.
Indication ThioTEPA is used a as conditioning treatment prior to allogeneic or autologous haematopoietic progenitor cell transplantation (HPCT) in haematological diseases in adult and paediatric patients. Also, when high dose chemotherapy with HPCT support it is appropriate for the treatment of solid tumours in adult and paediatric patients.
Pharmacology The unstable nitrogen-carbon groups alkylate with DNA causing irrepairable DNA damage. They stop tumor growth by crosslinking guanine nucleobases in DNA double-helix strands, directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. These drugs act nonspecifically.
Affected Organisms
Humans and other mammals
Half Life 1.5 to 4.1 hours
Elimination Urinary excretion of 14C-labeled thiotepa and metabolites in a 34-year old patient with metastatic carcinoma of the cecum who received a dose of 0.3 mg/kg intravenously was 63%.
Clearance * 446 +/- 63 mL/min [female patients (45 to 84 years) with advanced stage ovarian cancer receiving 60 mg and 80 mg thiotepa by intravenous infusion on subsequent courses given at 4-week intervals]
References
Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68. [Pubmed]
Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1775 external link
Research Area: Cancer
Biological Activity:
Thiotepa(Thioplex) is an alkylating agent used to treat cancer.. It is an analogue of N,N’,N’’- triethylenephosphoramide (TEPA). This molecule features tetrahedral phosphorus and is structurally akin to phosphate. It is derived from aziridine and thiophosphoryl chloride. Thiotepa has been previously used in the palliation of a wide variety of neoplastic diseases. The more consistent results have been seen in: adenocarcinoma of the breast, adenocarcinoma of the ovary, superficial papillary carcinoma of the urinary bladder and for controlling intracavitary effusions secondary to diffuse or localized neoplastic diseases of various serosal cavities. [1]
Sigma Aldrich -  T6069 external link
Application
Thio-TEPA (N,N’N’-triethylenethiophosphoramide) is used as a cancer chemotherapeutic, alkylating agent. It is used to treat various kinds of cancer such as breast, ovarian and bladder cancer. It is also used as conditioning treatment prior to haematopoietic progenitor cell transplantation (HPCT)1,2.
Biochem/physiol Actions
The unstable nitrogen-carbon groups alkylate with DNA which causes irreversible DNA damage. They stop tumor growth by crosslinking guanine nucleobases in DNA double-helix strands, directly attacking DNA. The DNA strands are unable to uncoil and separate which halts cell division1.
Toronto Research Chemicals -  T776650 external link
This substance is listed as a known human carcinogen. It is useful for the treatment of cancers, especially cancers resistant to chemotherapy. Antineoplastic.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68. Pubmed
  • Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68. Pubmed
  • http://en.wikipedia.org/wiki/Thiotepa
  • Kyriakou, C., et al.: J. Clin. Oncol., 27, 3262 (2009)
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专利

专利

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