Cyclophosphamide monohydrate 环磷酰胺
CAS 6055-19-2 MFCD00149395
化学结构图
SMILES: O.O=P1(N(CCCl)CCCl)NCCCO1
化学属性
| Mol. Formula | C7H15Cl2N2O2P·H2O |
|---|---|
| Mol. Weight | 279 |
| Melting Point | 49-51 |
| TSCA | No |
| Density | 1.422 |
| Solubility | Soluble in water (30 mg/ml), ethanol (slightly soluble), benzene (slightly soluble), ethylene glycol (slightly soluble), carbon tetrachloride (slightly soluble), dioxane (slightly soluble), ether (sparingly soluble), acetone (sparingly soluble), alcohol, |
| Boiling Point | 110°C |
| Flash Point | 113°(235°F) |
| Appearance | 白色结晶或结晶性粉末。熔点41-45℃。水中溶解度40g/L，微溶于醇、苯、乙二醇、四氯化碳、二氧六圜，几乎不溶于乙醚及丙酮。失去结晶水即液化，水溶液不稳定。无臭、味微苦。 |
| Stability | 对热、光线、空气敏感 |
别名和识别编码
| Chemical Name | Cyclophosphamide monohydrate |
|---|---|
| CAS Number | 6055-19-2 |
| Synonym | (+,-)-2-(bis(2-Chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-Oxide Monohydrate (bis(chloro-2-ethyl)amino)-2-tetrahydro-3 1-(bis(2-chloroethyl)amino)-1-oxo-2-aza-5-oxaphosphoridine 2-(bis(2-chloroethyl)amino)-1-oxa-3-aza-2-phosphocyclohexane2-oxidemonohydr 2-(di(2-chloroethyl 2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide, Cytoxan 2H-1,3,2-Oxazaphospho B 518 B-518 B518 Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester CYTOXAN Cyclophosphamide Cyclophosphamide Anhydrous Cyclophosphamide Monohydrate Cyclophosphamide, (R)-Isomer Cyclophosphamide, (S)-Isomer Cyclophosphane Cyclophosphane monohydrate Cytophosphan Cytophosphane Cytoxan Endoxan Mitoxan N,N-双( |
| PubChem Substance ID | 22420 |
| EC Number | 200-015-4 |
| Beilstein Registry Number | 8167897 |
| MDL Number | MFCD00149395 |
| Reaxys-RN | 8167897 |
| Merck Number | 2747 |
| Chemical Name Translation | 环磷酰胺 |
| LabNetwork Molecule ID | LN00222334 |
| InChI | InChI=1S/C7H15Cl2N2O2P.H2O/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14;/h1-7H2,(H,10,12);1H2 |
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分类
- {SNA} Analytical Standards, EP Standards, EP Standards C
- {SA} ALDH1A, Apoptosis Reagents, Apoptosis and Cell Cycle, Bioactive Small Molecules, Breast Cancer Stem Cell Markers, CI-CY, Cancer Research, Cancer Stem Cells, Cell Biology, Cell Signaling and Neuroscience, DNA Intercalators and Crosslinkers, DNA metabolism, Other Apoptosis Related Reagents
- {SNA} Analytical Standards, Chromatography, EP Standards, EP Standards C - D, Pharmaceutical Standards, Pharmacopeia Standards, 分析/色谱
- {SNA} DNA Modification / Repair, 抗肿瘤药物, 癌症研究,
- {SNA} ALDH1A,
产品应用
- An immunosuppressive, cytotoxic apoptosis inducer.
相关文献及参考
- Merck: 14,2747
- Wheeler, A.G., et al.: Toxicol. Appl. Pharmacol., 4, 324 (1962),
- Guerriero, J.L., et al., DNA Alkylating Therapy Induces Tumor Regression Through An HMGB1-Mediated Activation Of Innate Immunity. J. Immunol. 186 , 3517-26, (2011) 摘要
- Colvin, O.M., et al.: Curr. Pharmaceut. Design, 5, 555 (1999),
- Tammam, J., et al., Down-regulation Of The Notch Pathway Mediated By A Gamma-secretase Inhibitor Induces Anti-tumour Effects In Mouse Models Of T-cell Leukaemia. Br. J. Pharmacol. 158 , 1183-95, (2009) 摘要
- Fraiser, L.H., et al.: Drugs, 42, 781 (1991),
- Inagawa, H., et al., Mechanisms by which chemotherapeutic agents augment the antitumor effects of tumor necrosis factor: involvement of the pattern shift of cytokines from Th2 to Th1 in tumor lesions. Anticancer Res. 18 , 3957-3964, (1998)
- Short: III/10a
- Gibson, L.F., et al., Regulation of BAX and BCL-2 expression in breast cancer cells by chemotherapy. Breast Cancer Res. Treat. 55 , 107-117, (1999)
- Ren, S., et al., Inhibition of human aldehyde dehydrogenase 1 by the 4-hydroxycyclophosphamide degradation product acrolein. Drug Metab. Dispos. 27 , 133-137, (1999) 摘要
- Merck 14 ,2747
安全信息
GHS Symbol
- H301 Toxic if swallowed 吞食有毒
- H302 Harmful if swallowed 吞食有害
- H318 Causes serious eye damage 严重伤害眼睛
- H340 May cause genetic defects 可能导致遗传性缺陷
- H350 May cause cancer 可能致癌
- H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
- H372 Causes damage to organs through prolonged or repeated exposure 长期或频繁接触会损伤器官
- H413 Maycauselonglastingharmfuleffectstoaquaticlife 可能对水生生物造成长期持续有害影响。
- P201 Obtain special instructions before use. 使用前获取专门指示。
- P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
- P203
- P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P263 Avoid contact during pregnancy/while nursing. 怀孕/哺乳期间避免接触。
- P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
- P264+P265
- P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
- P273 Avoid release to the environment. 避免释放到环境中。
- P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
- P281 Use personal protective equipment as required. 使用所需的个人防护装备。
- P301+P310
- P301+P310+P330
- P301+P312
- P301+P316
- P301+P317
- P302+P350
- P302+P352+P332+P313+P362+P364
- P305+P351+P338
- P305+P354+P338
- P307+P311
- P308+
- P308+P313
- P308+P316
- P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
- P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医，如果你觉得不舒服
- P317
- P318
- P319
- P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
- P330 Rinse mouth. 漱口
- P332+P313
- P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
- P405 Store locked up. 上锁保管。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
- S20 When using do not eat or drink 使用时，不得进食，饮水；
- S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
- S36 Wear suitable protective clothing 穿戴适当的防护服；
- S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护；
- S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
- S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
- S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
- R25 Toxic if swallowed 吞咽有毒
- R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
- R45 May cause cancer 可能致癌
- R46 May cause inheritable genetic damage 可能引起遗传基因损害
- R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSE
{hazarTYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 40 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : DMWOAX Deutsche Medizinische Wochenschrift. (Stuttgart, Fed. Rep. Ger.) V.1-104, 1875-1979. Volume(issue)/page/year: 83,453,1958
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 130 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : DMWOAX Deutsche Medizinische Wochenschrift. (Stuttgart, Fed. Rep. Ger.) V.1-104, 1875-1979. Volume(issue)/page/year: 83,453,1958
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 94 mg/kg TOXIC EFFECTS : Behavioral - ataxia Kidney, Ureter, Bladder - urine volume increased Blood - hemorrhage REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 4,324,1962
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 400 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : DMWOAX Deutsche Medizinische Wochenschrift. (Stuttgart, Fed. Rep. Ger.) V.1-104, 1875-1979. Volume(issue)/page/year: 83,453,1958
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF E
TYPE OF TEST : Sister chromatid exchange ROUTE OF EXPOSURE : Intraperitoneal TEST SYSTEM : Rodent - mouse DOSE/DURATION : 50 umol/kg REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 222,271,1989
TYPE OF TEST : Micronucleus test ROUTE OF EXPOSURE : Oral TEST SYSTEM : Rodent - mouse DOSE/DURATION : 15 mg/kg REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 234,169,1990
TYPE OF TEST : Micronucleus test ROUTE OF EXPOSURE : Multiple routes TEST SYSTEM : Non-mammalian species DOSE/DURATION : 5 ppm REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 292,83,1993
TYPE OF TEST : Sperm Morphology ROUTE OF EXPOSURE : Intraperitoneal TEST SYSTEM : Rodent - mouse DOSE/DURATION : 100 mg/kg/5D (Continuous) REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 69,149,1980
TYPE OF TEST : Micronucleus test ROUTE OF EXPOSURE : Multiple routes TEST SYSTEM : Non-mammalian species DOSE/DURATION : 500 ppb REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 292,83,1993
TYPE OF TEST : Unscheduled DNA synthesis ROUTE OF EXPOSURE : Intraperitoneal TEST SYSTEM : Rodent - rat DOSE/DURATION : 200 mg/kg REFERENCE : MUREAV Mutation Research.
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE : 321 mg/kg SEX/DURATION : male 9 week(s) pre-mating TOXIC EFFECTS : Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 229,129,1990
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE : 88 mg/kg SEX/DURATION : male 9 week(s) pre-mating TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 229,129,1990
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE : 27500 ug/kg SEX/DURATION
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE : 40 mg/kg SEX/DURATION : female 14 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - blood and lymphatic systems (including spleen and marrow) Reproductive - Specific Developmental Abnormalities - hepatobiliary system REFERENCE : EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 18,1,1991
{ha其他信息
- 微溶于水，微溶于醇、苯、乙二醇、四氯化碳、二氧六圜，几乎不溶于乙醚及丙酮,失去结晶水即液化，水溶液不稳定,无臭、味微苦。
- MOL 文件:6055-19-2.mol
- 用途一:抗肿瘤药。用于恶性淋巴瘤效果好，对急性淋巴白血病也具一定疗效，其他对慢性淋巴细胞白血病、乳癌、卵巢癌、睾丸癌、多发性骨髓瘤、神经母细胞瘤、头颈部癌和结肠癌等也有效。本品尚有免疫抑制作用。用于肾病缩合症和类风湿性关节炎等。该品毒性，对老鼠口服LD50为35094mg/kg。
- MSDS 信息:N,N-Bis(beta-chloroethyl)-N',O-propylenephosphoric acid ester amide monohydrate(6055-19-2).msds
- 环磷酰胺价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 K2987501 环磷酰胺，一水 （+4℃） 1g 941元 2011/04/16 C2236 环磷酰胺单水合物 Cyclophosphamide Monohydrate 25G 3550元 2011/04/16 C2236 环磷酰胺单水合物 Cyclophosphamide Monohydrate 5G 1050元
- 上游原料:二乙醇胺
- Cyclophosphamide monohydrate is an alkylating, cytotoxic agent experimentally shown to crosslink DNA, causing strand breakage and inducing mutations. It is also believed to possess immunosuppressive properties. Cyclophosphamide Monohydrate inhibits ALDH1 (aldehyde dehydrogenase 1) through its degradation product acrolein, as well as induces apoptosis in the rat thymus via the Fas/Fas ligand pathway.
- Acros Organics:环磷酰胺单水合物 Cyclophosphamide monohydrate, 97%(6055-19-2)
- 方法一:由二乙醇胺经氯化、缩合、环合而得。
- Sigma Aldrich:6055-19-2(sigmaaldrich)
- Alfa Aesar:环磷酰胺 Cyclophosphamide monohydrate, 97+%(6055-19-2)
- F:10
- 用途二:环磷酰胺是一种细胞毒性物，广泛地用于癌症化疗。它交联DNA，引起DNA链断裂，从而诱发突变。它的临床活性和醛脱氢酶（aldehyde dehydrogenase 1，ALDH1)活性的减少密切相关。
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