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55-98-1 分子结构
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4-(methanesulfonyloxy)butyl methanesulfonate

ChemBase编号:881
分子式:C6H14O6S2
平均质量:246.30176
单一同位素质量:246.02318017
SMILES和InChIs

SMILES:
S(=O)(=O)(OCCCCOS(=O)(=O)C)C
Canonical SMILES:
CS(=O)(=O)OCCCCOS(=O)(=O)C
InChI:
InChI=1S/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3
InChIKey:
COVZYZSDYWQREU-UHFFFAOYSA-N

引用这个纪录

CBID:881 http://www.chembase.cn/molecule-881.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-(methanesulfonyloxy)butyl methanesulfonate
IUPAC传统名
busulfan
商标名
Busulfex
Citosulfan
Leucosulfan
Mablin
Mielevcin
Mielosan
Mielucin
Milecitan
Mileran
Misulban
Mitosan
Mitostan
Myeleukon
Myeloleukon
Myelosan
Mylecytan
Myleran
Myleran Tablets
别名
1,4-丁二醇二甲烷磺酸盐
白消安
白消安
1,4-双(甲基磺酰氧)丁烷
1,4-Butanediol-dimethanesulfonate Esters
CB-2041
GT-41
Misulban
Busulfan
4-(methanesulfonyloxy)butyl methanesulfonate
1,4-Butanediol dimethanesulfonate
1,4-Butanediol dimethanesulfonate
Butanedioldimethanesulfonate
Busulphan
Busulphane
Buzulfan
Sulfabutin
Sulphabutin
Tetramethylene Dimethane Sulfonate
Tetramethylenester Kyseliny Methansulfonove
busulfan
Busulfan
Myleran
Busulfex
CAS号
55-98-1
EC号
200-250-2
MDL号
MFCD00007562
Beilstein号
1791786
PubChem SID
160964344
46506234
24891664
PubChem CID
2478

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) -0.7590282  LogD (pH = 7.4) -0.7590282 
Log P -0.7590282  摩尔折射率 49.5686 cm3
极化性 21.777626 Å3 极化表面积 86.74 Å2
可自由旋转的化学键 里宾斯基五规则 true 
Log P -0.9  LOG S -1.68 
溶解度 5.16e+00 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
6.9E+004 mg/L expand 查看数据来源
Acetonitrile expand 查看数据来源
DMSO expand 查看数据来源
Methanol expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
114 - 117°C expand 查看数据来源
114-116°C expand 查看数据来源
114-117 °C(lit.) expand 查看数据来源
114-118 expand 查看数据来源
115-117 °C expand 查看数据来源
疏水性(logP)
-0.3 expand 查看数据来源
-0.592 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Hygroscopic, Refrigerator, Under Inert Atmosphere expand 查看数据来源
Room Temperature (15-30°C) expand 查看数据来源
RTECS编号
EK1750000 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
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)
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
45-26/27/28 expand 查看数据来源
R:45 expand 查看数据来源
安全公开号
53-36/37/39-45 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-H310-H330-H350 expand 查看数据来源
GHS警示性声明
P201-P260-P280-P284-P301 + P310-P302 + P350 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
相关基因信息
human ... CYP1A2(1544) expand 查看数据来源
纯度
≥99.0% (CH) expand 查看数据来源
95% expand 查看数据来源
级别
analytical standard, for drug analysis expand 查看数据来源
purum 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
下载链接 expand 查看数据来源
线性分子式
CH3SO2O(CH2)4OSO2CH3 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02154906 external link
(1,4-Butanediol dimethanesulfonate)
DrugBank -  DB01008 external link
Item Information
Drug Groups approved; investigational
Description An alkylating agent having a selective immunosuppressive effect on bone marrow. It has been used in the palliative treatment of chronic myeloid leukemia (myeloid leukemia, chronic), but although symptomatic relief is provided, no permanent remission is brought about. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), busulfan is listed as a known carcinogen. [PubChem]
Indication For use in combination with cyclophosphamide as a conditioning regimen prior to allogeneic hematopoietic progenitor cell transplantation for chronic myelogenous leukemia (FDA has designated busulfan as an orphan drug for this use). Also used as a component of pretransplant conditioning regimens in patients undergoing bone marrow transplantation for acute myeloid leukemia and nonmalignant diseases.
Pharmacology Busulfan 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 leads to a miscoding of DNA. Alkylating agents are cell cycle-nonspecific and work by three different mechanisms, all of which achieve the same end result - disruption of DNA function and cell death.
Toxicity Signs of overdose include allergic reaction, unusual bleeding or bruising, sudden weakness or unusual fatigue, persistent cough, congestion, or shortness of breath; flank, stomach or joint pain; pronounced nausea, vomiting, diarrhea, dizziness, confusion, or darkening of the skin, chills, fever, collapse, and loss of consciousness.
Affected Organisms
Humans and other mammals
Biotransformation Mainly Hepatic. Busulfan is predominantly metabolized by conjugation with glutathione, both spontaneously and by glutathione S-transferase (GST) catalysis.
Absorption Completely absorbed from the gastrointestinal tract.
Half Life 2.5 hours
Protein Binding 32.4%
Elimination Following administration of 14C- labeled busulfan to humans, approximately 30% of the radioactivity was excreted into the urine over 48 hours; negligible amounts were recovered in feces.
Clearance * 2.52 ml/min/kg [Following an infusion of dose of 0.8 mg/kg every six hours, for a total of 16 doses over four days]
References
Lesurtel M, Graf R, Aleil B, Walther DJ, Tian Y, Jochum W, Gachet C, Bader M, Clavien PA: Platelet-derived serotonin mediates liver regeneration. Science. 2006 Apr 7;312(5770):104-7. [Pubmed]
Valdez BC, Andersson BS: Interstrand crosslink inducing agents in pretransplant conditioning therapy for hematologic malignancies. Environ Mol Mutagen. 2010 Jul;51(6):659-68. [Pubmed]
Hall AG, Tilby MJ: Mechanisms of action of, and modes of resistance to, alkylating agents used in the treatment of haematological malignancies. Blood Rev. 1992 Sep;6(3):163-73. [Pubmed]
Ciurea SO, Andersson BS: Busulfan in hematopoietic stem cell transplantation. Biol Blood Marrow Transplant. 2009 May;15(5):523-36. Epub 2009 Feb 12. [Pubmed]
McCune JS, Holmberg LA: Busulfan in hematopoietic stem cell transplant setting. Expert Opin Drug Metab Toxicol. 2009 Aug;5(8):957-69. [Pubmed]
Krivoy N, Hoffer E, Lurie Y, Bentur Y, Rowe JM: Busulfan use in hematopoietic stem cell transplantation: pharmacology, dose adjustment, safety and efficacy in adults and children. Curr Drug Saf. 2008 Jan;3(1):60-6. [Pubmed]
Nath CE, Shaw PJ: Busulphan in blood and marrow transplantation: dose, route, frequency and role of therapeutic drug monitoring. Curr Clin Pharmacol. 2007 Jan;2(1):75-91. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1692 external link
Research Area: Cardiovascular Disease
Biological Activity:
Busulfan(Myleran, Busulfex) is a cell cycle non-specific alkylating antineoplastic agent, in the class of alkyl sulfonates. Its chemical designation is 1,4-butanediol dimethanesulfonate. Its main uses are in bone marrow transplantation, especially in chronic myelogenous leukemia (CML), where it is used as a conditioning drug. Busulfan can control tumor burden but cannot prevent transformation or correct cytogenic abnormalities. Though not as common, it may also be used for chronic lymphocytic leukemia (CLL). [1]
Sigma Aldrich -  B2635 external link
包装
10, 25 g in poly bottle
Toronto Research Chemicals -  B689900 external link
Alkylating agent with antileukemic activity. Antineoplastic.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Lesurtel M, Graf R, Aleil B, Walther DJ, Tian Y, Jochum W, Gachet C, Bader M, Clavien PA: Platelet-derived serotonin mediates liver regeneration. Science. 2006 Apr 7;312(5770):104-7. Pubmed
  • Valdez BC, Andersson BS: Interstrand crosslink inducing agents in pretransplant conditioning therapy for hematologic malignancies. Environ Mol Mutagen. 2010 Jul;51(6):659-68. Pubmed
  • Hall AG, Tilby MJ: Mechanisms of action of, and modes of resistance to, alkylating agents used in the treatment of haematological malignancies. Blood Rev. 1992 Sep;6(3):163-73. Pubmed
  • Ciurea SO, Andersson BS: Busulfan in hematopoietic stem cell transplantation. Biol Blood Marrow Transplant. 2009 May;15(5):523-36. Epub 2009 Feb 12. Pubmed
  • McCune JS, Holmberg LA: Busulfan in hematopoietic stem cell transplant setting. Expert Opin Drug Metab Toxicol. 2009 Aug;5(8):957-69. Pubmed
  • Krivoy N, Hoffer E, Lurie Y, Bentur Y, Rowe JM: Busulfan use in hematopoietic stem cell transplantation: pharmacology, dose adjustment, safety and efficacy in adults and children. Curr Drug Saf. 2008 Jan;3(1):60-6. Pubmed
  • Nath CE, Shaw PJ: Busulphan in blood and marrow transplantation: dose, route, frequency and role of therapeutic drug monitoring. Curr Clin Pharmacol. 2007 Jan;2(1):75-91. Pubmed
  • http://en.wikipedia.org/wiki/Busulfan
  • Ehrsson, H., et al.: Clin. Pharmacol. Ther., 34, 86 (1983)
  • Bishop, J.B., et al.: Mutat. Res., 168,15 (1983)
  • Tariq, M., et al.: Anal. Profiles Drug Subs., 16, 53 (1983)
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专利

专利

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