2-[bis(2-chloroethyl)amino]-1,3,2$l^{5}-oxazaphosphinan-2-one

• ChemBase编号: 413
• 分子式: C7H15Cl2N2O2P
• 平均质量: 261.085961
• 单一同位素质量: 260.02481972
• SMILES: ClCCN(P1(=O)OCCCN1)CCCl
• Canonical SMILES: ClCCN(P1(=O)NCCCO1)CCCl
• InChI: InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
• InChIKey: CMSMOCZEIVJLDB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-[bis(2-chloroethyl)amino]-1,3,2$l^{5}-oxazaphosphinan-2-one; 2-[bis(2-chloroethyl)amino]-1,3,2λ^5-oxazaphosphinan-2-one
• IUPAC传统名: cyclophosphamide; cyclophosphamide, (+-)-
• 商标名: ASTA; Asta B 518; CP; CPA; CTX; CY; Clafen; Claphene; Cyclophosphamid; Cyclophosphamide Monohydrate; Cyclophosphamide Sterile; Cyclophosphamidum; Cyclophosphan; Cyclophosphane; Cyclophosphoramide; Cyclostin; Cyklofosfamid; Cytophosphan; Cytoxan; Cytoxan Lyoph; Endoxan; Endoxan R; Endoxan-Asta; Endoxana; Endoxanal; Endoxane; Enduxan; Genoxal; Hexadrin; Lyophilized Cytoxan; Mitoxan; Neosar; Procytox; Rcra Waste Number U058; Semdoxan; Sendoxan; Senduxan; Zyklophosphamid; Revimmune; Lyophilizedcytoxan
• 别名: 环磷酰胺 单水合物; cyclophosphamide; Cyclophosphamide; Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester; Cyclophosphane; Cyclophosphamide monohydrate; Endoxan; Cytoxan; Neosar; Clafen(Cyclophosphamide); 2-[bis(2-chloroethyl)amino]-1,3,2$l^{5}-oxazaphosphinan-2-one

登记号

• CAS号: 50-18-0; 6055-19-2
• EC号: 200-015-4
• MDL号: MFCD00005978; MFCD00149395
• Beilstein号: 8167897
• 默克索引号: 142747
• PubChem SID: 46505441; 160963876
• PubChem CID: 2907
• CHEBI ID: 4027
• ATC码: L01AA01
• CHEMBL: 88
• Chemspider ID: 2804
• DrugBank ID: DB00531
• KEGG ID: D07760
• 美国药典/FDA物质标识码: 6UXW23996M
• 维基百科标题: Cyclophosphamide
• Medline Plus: a682080

理论计算性质

JChem

• Acid pKa: 12.076543
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 0.09654615
• LogD (pH = 7.4): 0.096539564
• Log P: 0.096547686
• 摩尔折射率: 58.4781 cm^3
• 极化性: 23.373837 Å^3
• 极化表面积: 41.57 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.76
• LOG S: -1.24
• 溶解度: 1.51e+01 g/l

分子性质

理化性质

• 溶解度: Soluble. 1-5 g/100 mL at 23 oC
• 熔点: 2°C (35.6°F); 51-53°C
• 疏水性(logP): 0.8; 0.803

安全信息

• 保存条件: -20°C
• RTECS编号: RP6157750
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: UN3464
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): II
• 危险公开号: 45-46-61-25
• 安全公开号: 53-20-36-45-60
• TSCA收录: 否
• GHS危险品标识: GHS06; GHS08
• GHS危险声明: H301-H340-H350-H360
• GHS警示性声明: P281-P301+P310-P321-P308+P313-P405-P501A

药理学性质

• 作用靶点: DNA/RNA synthesis
• 给药途径: Oral, intravenous
• 生物利用度: >75% (oral)
• 排泄: Renal
• 半衰期: 3-12 hours
• 代谢: Hepatic
• 蛋白结合率: >60%
• 法定药品分级: Rx-only
• 妊娠期药物分类: D (Australia); D (US)

产品相关信息

• 纯度: 95%; 97+%
• 成盐信息: Free Base

详细说明

DrugBank - DB00531

• Drug Groups: approved; investigational
• Description: Precursor of an alkylating nitrogen mustard antineoplastic and immunosuppressive agent that must be activated in the liver to form the active aldophosphamide. It has been used in the treatment of lymphoma and leukemia. Its side effect, alopecia, has been used for defleecing sheep. Cyclophosphamide may also cause sterility, birth defects, mutations, and cancer. [PubChem]
• Indication: For management of malignant lymphomas, multiple myeloma,leukemias, mycosis fungoides (advanced disease), neuroblastoma (disseminated disease), adenocarcinoma of the ovary, retinoblastoma and carcinoma of the breast
• Pharmacology: Cyclophosphamide is an antineoplastic in the class of alkylating agents and 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.
• Toxicity: infection, myelosuppression, and cardiac toxicity
• Affected Organisms: Humans and other mammals
• Biotransformation: hepatic
• Absorption: 90-100%
• Half Life: 3-12 hours
• Protein Binding: >60%
• Elimination: It is eliminated primarily in the form of metabolites, but from 5% to 25% of the dose is excreted in urine as unchanged drug.
• References: Brock N: The history of the oxazaphosphorine cytostatics. Cancer. 1996 Aug 1;78(3):542-7. [Pubmed] ; Brock N: Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture. Cancer Res. 1989 Jan 1;49(1):1-7. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1217

Research Area: Cancer
Biological Activity:
Cyclophosphamide is a synthetic alkylating agent chemically related to the nitrogen mustards with antineoplastic and immunosuppressive activities. In the liver, cyclophosphamide is converted to the active metabolites aldophosphamide and phosphoramide mustard, which bind to DNA, thereby inhibiting DNA replication and initiating cell death. [1]Cyclophosphamide is given as a treatment for many types of cancer, among them lymphomas, ovary, breast, and bladder; and chronic lymphocytic leukaemia. [2]This agent inhibited cell proliferation of NCI-H727 with IC50 at 9.3 nM. [3]

参考文献

• Brock N: The history of the oxazaphosphorine cytostatics. Cancer. 1996 Aug 1;78(3):542-7. Pubmed
• Brock N: Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture. Cancer Res. 1989 Jan 1;49(1):1-7. Pubmed
• http://en.wikipedia.org/wiki/Cyclophosphamide