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305-03-3 分子结构
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4-{4-[bis(2-chloroethyl)amino]phenyl}butanoic acid

ChemBase编号:176
分子式:C14H19Cl2NO2
平均质量:304.21216
单一同位素质量:303.07928421
SMILES和InChIs

SMILES:
ClCCN(c1ccc(CCCC(=O)O)cc1)CCCl
Canonical SMILES:
ClCCN(c1ccc(cc1)CCCC(=O)O)CCCl
InChI:
InChI=1S/C14H19Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h4-7H,1-3,8-11H2,(H,18,19)
InChIKey:
JCKYGMPEJWAADB-UHFFFAOYSA-N

引用这个纪录

CBID:176 http://www.chembase.cn/molecule-176.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-{4-[bis(2-chloroethyl)amino]phenyl}butanoic acid
IUPAC传统名
chlorambucil
商标名
Ambochlorin
Amboclorin
Ecloril
Elcoril
Leukeran
Leukeran Tablets
Leukersan
Leukoran
Linfolizin
Linfolysin
Pepstatin
别名
4-(4-[Bis(2-chloroethyl)amino]phenyl)butyric acid
Chlorambucil
4-(p-[bis-(2-Chloroethyl)-amino]-phenyl)-butyric acid
4-[Bis(2-chloroethyl)amino]benzenebutyric acid
Chloraminophen
Chloraminophene
Phenylbutyric Acid Nitrogen Mustard
Chlorobutine
Chlorobutin
Chloroambucil
Chlorbutine
Chlorbutin
Chlocambucil
Chlorambucil
CAS号
305-03-3
EC号
206-162-0
MDL号
MFCD00021783
Beilstein号
999011
PubChem SID
24278287
24853850
46506842
160963639
PubChem CID
2708
CHEBI ID
28830
ATC码
L01AA02
CHEMBL
515
Chemspider ID
2607
DrugBank ID
DB00291
KEGG ID
D00266
美国药典/FDA物质标识码
18D0SL7309
维基百科标题
Chlorambucil
Medline Plus
a682899

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 4.4555492  质子受体
质子供体 LogD (pH = 5.5) 2.8512278 
LogD (pH = 7.4) 1.0883248  Log P 3.937155 
摩尔折射率 79.6828 cm3 极化性 30.39351 Å3
极化表面积 40.54 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 3.81  LOG S -3.59 
溶解度 7.73e-02 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
1.24E+004 mg/L expand 查看数据来源
熔点
64-66°C expand 查看数据来源
65-70 °C expand 查看数据来源
蒸汽压
5.7 x 10-8 mm Hg at 25 °C expand 查看数据来源
疏水性(logP)
3.9 expand 查看数据来源
保存条件
2-8°C expand 查看数据来源
RTECS编号
ES7525000 expand 查看数据来源
欧盟危险性物质标志
有毒(Toxic) 有毒(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
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
III expand 查看数据来源
澳大利亚Hazchem
2X expand 查看数据来源
危险公开号
45-25-36/37/38 expand 查看数据来源
R:25-45 expand 查看数据来源
安全公开号
53-26-45 expand 查看数据来源
S:28-36/37/39-45-53 expand 查看数据来源
欧盟危险货物分类
T2 expand 查看数据来源
欧盟危险识别号(EUHIN)
6.1B expand 查看数据来源
美国ERG指导号
154 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
H301-H315-H319-H335-H350 expand 查看数据来源
GHS警示性声明
P201-P261-P301 + P310-P305 + P351 + P338-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 3 expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
给药途径
Oral expand 查看数据来源
排泄
N/A expand 查看数据来源
半衰期
1.5 hours expand 查看数据来源
代谢
Hepatic expand 查看数据来源
法定药品分级
Rx-only expand 查看数据来源
妊娠期药物分类
D (US) expand 查看数据来源
相关基因信息
human ... CYP2D6(1565) expand 查看数据来源
纯度
≥98.0% (T) expand 查看数据来源
级别
purum 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)
C14H19Cl2NO2 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals -  02101346 external link
Alkylating antitumor agent.
Can be covalently coupled to monoclonal anticarcinombryonic antigen.
DrugBank -  DB00291 external link
Item Information
Drug Groups approved
Description A nitrogen mustard alkylating agent used as antineoplastic agent for the treatment of various malignant and nonmalignant diseases. Although it is less toxic than most other nitrogen mustards, it has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (Merck Index, 11th ed)
Indication For treatment of chronic lymphatic (lymphocytic) leukemia, childhood minimal-change nephrotic syndrome, and malignant lymphomas including lymphosarcoma, giant follicular lymphoma, Hodgkin's disease, non-Hodgkin's lymphomas, and Waldenstr?m’s Macroglobulinemia.
Pharmacology Chlorambucil is an antineoplastic in the class of alkylating agents that is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases 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. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Alkylating agents are cell cycle-nonspecific. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death.
Affected Organisms
Humans and other mammals
Half Life 1.5 hours
Protein Binding 99%
Elimination Chlorambucil is extensively metabolized in the liver primarily to phenylacetic acid mustard. The pharmacokinetic data suggests that oral chlorambucil undergoes rapid gastrointestinal absorption and plasma clearance and that it is almost completely metabolized, having extremely low urinary excretion.
References
Rai KR, Peterson BL, Appelbaum FR, Kolitz J, Elias L, Shepherd L, Hines J, Threatte GA, Larson RA, Cheson BD, Schiffer CA: Fludarabine compared with chlorambucil as primary therapy for chronic lymphocytic leukemia. N Engl J Med. 2000 Dec 14;343(24):1750-7. [Pubmed]
Yang K, Tan J, Wu T: Alkylating agents for Waldenstrom's macroglobulinaemia. Cochrane Database Syst Rev. 2009 Jan 21;(1):CD006719. [Pubmed]
Foon KA, Hallek MJ: Changing paradigms in the treatment of chronic lymphocytic leukemia. Leukemia. 2010 Mar;24(3):500-11. Epub 2009 Dec 24. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich -  C0253 external link
Biochem/physiol Actions
Chlorambucil is an anti-cancer drug that alkylates DNA and induces apoptosis. Death of chronic lymphocytic leukemia cells occurs via a p53-dependent mechanism.
Sigma Aldrich -  23125 external link
Other Notes
Alkylating antitumor agent, can be covalently coupled to monoclonal anticarcinoembryonic antigen1

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Bernier, L.G., et al., Protides Biol. Fluids , 31 : 787 (1983).
  • Rai KR, Peterson BL, Appelbaum FR, Kolitz J, Elias L, Shepherd L, Hines J, Threatte GA, Larson RA, Cheson BD, Schiffer CA: Fludarabine compared with chlorambucil as primary therapy for chronic lymphocytic leukemia. N Engl J Med. 2000 Dec 14;343(24):1750-7. Pubmed
  • Yang K, Tan J, Wu T: Alkylating agents for Waldenstrom's macroglobulinaemia. Cochrane Database Syst Rev. 2009 Jan 21;(1):CD006719. Pubmed
  • Foon KA, Hallek MJ: Changing paradigms in the treatment of chronic lymphocytic leukemia. Leukemia. 2010 Mar;24(3):500-11. Epub 2009 Dec 24. Pubmed
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