Cyclophosphamide 环磷酰胺

CAS 50-18-0 MFCD00005978

化学结构图

50-18-0
SMILES: O=P1(N(CCCl)CCCl)NCCCO1

化学属性

Mol. FormulaC7H15Cl2N2O2P
Mol. Weight261.11
Melting Point49.2-52.8 °C
Solubility25°C: DMSO 52mg/mL; Water 43 mg/mL; Ethanol 52 mg/mL

别名和识别编码

Chemical NameCyclophosphamide
Synonym (+,-)-2-(bis(2-Chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-Oxide Monohydrate (Bis(chloro-2-ethyl)amino)-2-tetrahydro-3,4,5,6-oxazaphosphorine-1,3,2-oxide-2 hydrate 1-(Bis(2-chloroethyl)amino)-1-oxo-2-aza-5-oxaphosphoridine; 2-(Di(2-chloroethyl)amino)-1-oxa-3-aza-2-phos 2-(Bis(2-chloroethyl)amino)-2H-1,3,2-oxazaphosphorine 2-oxide 2-H-1,3,2-Oxazaphosphorinane 2-[bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide 2H-1,3,2-Ox 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis[2-chloroethyl]tetrahydro-, 2-oxide 2H-1,3,2-Oxazaphosphorine, 2-(bis(2-chloroethyl)amino)tetrahydro-,2-oxide ASTA ASTA B518 Asta B 518 {PubChem
EC Number200-015-4
CAS Number50-18-0
Chemical Name Translation环磷酰胺
Wiswesser Line NotationT6MPOTJ BO BN2G2G
Beilstein Registry Number0011744
LabNetwork Molecule IDLN01343512
PubChem Substance ID2907
InChIInChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
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分类

  • {uni_hamburg} no charge; oxygen heterocycle; nitrogen heterocycle; other heterocycle; alicycle; 6RingOnly; 6ring; racemate; 1fragment

产品应用

  • An anti-proliferative agent that regulates Bax and Bcl-2 expression.

相关文献及参考

  • Short: III/20a Title: Nuclear Quadrupole Resonance Spectroscopy Data: Nuclei D ... Cl Author: Chihara, H.; Nakamura, N. Editor: Hellwege, K.-H.; Hellwege, A.M. Source: Landolt-Börnstein, New Series Volume: III/20a Year: 1988 Keyword: NQR ISBN: 3-540-18161-X ISBN: 978-3-540-18161-3 Internet Resource: DOI:10.1007/b31153 RefComment: IX,677 pages. Hardcover Abstract: Nuclear Quadrupole Resonance Spectroscopy has become a standard method for structural research in molecular and solid state physics as well as for different branches of chemistry. The volumes cover data for more than 8,000 substances in the solid state. Data for free molecules have been published in volumes II/14 and II/15 of the New Series. The tables are arranged according to the atomic number of the elements.
  • Short: IV/8A Title: Enthalpies of Fusion and Transition of Organic Compounds Author: Zhang, Z.-Y.; Frenkel, M.; March, K.N.; Wilhoit, R.C. Editor: Marsh, K.N. Source: Landolt-Börnstein, New Series Volume: IV/8A Year: 1995 Keyword: organic compounds; enthaly of fusion; melting point; phase transition ISBN: 3-540-58854-X ISBN: 978-3-540-58854-2 Internet Resource: DOI:10.1007/b55145 RefComment: VIII, 588 pages.
  • Short: EINECS Title: EINECS (European Inventory of Existing Commercial Chemical Substances) Source: Official Journal of the European Communities Volume: C 146 A (15.06.1990) Page: 1 Year: 1990 Internet Resource: http://ecb.jrc.ec.europa.eu/esis/index.php?PGM=ein Publish_Date: 1990/06/15

安全信息

Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
UN Number UN 1851 1851
Hazard Class6.1(b)
Packing GroupIII
Storage condition 储存温度-20°C 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1352 mg/kg/1Y-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Skin and Appendages - tumors
   Reproductive - Tumorigenic effects - ovarian tumors
REFERENCE :
   ARZNAD Arzneimittel-Forschung. Drug Research.  (Editio Cantor Verlag,
   Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.)  V.1-    1951-
   Volume(issue)/page/year: 20,1461,1970

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 676 mg/kg/1Y-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Brain and Coverings - tumors
   Kidney, Ureter, Bladder - Kidney tumors
REFERENCE :
   ARZNAD Arzneimittel-Forschung. Drug Research.  (Editio Can

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOS

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 857 mg/kg/3Y-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Blood - tumors
REFERENCE :
   JCPAAK Journal of Clinical Pathology.  (British Medical Journal, Box 560B,
   Kennebunkport, M

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 1800 mg/kg/6Y-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Kidney, Ureter, Bladder - tumors
REFERENCE :
   JOURAA Journal of Urology.  (Williams & Wilkins Co., 428 E. Preston St.,
   Baltimore, MD  21202) V.1-    1917-  Volume(issue)/page/year: 126,544,1981

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXP

RTECSRP5950000 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 110 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   FATOAO Farmakologiya i Toksikologiya (Moscow).  For English translation, see
   PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2-   
   1939-  Volume(issue)/page/year: 41,90,1978

TYPE OF TEST            : LD10 - Lethal Dose
ROUTE OF EXPOSURE       : Parenteral
SPECIES OBSERVED        : Rodent - hamster
DOSE/DURATION           : 110 mg/kg
TOXIC EFFECTS :
   Tumorigenic - active as anti-cancer agent
REFERENCE :
   JSONAU Journal of Surgical Oncology.  (Alan R. Liss, Inc., 41 E. 11th St.,
   New York, NY 10003) V.1-    1969-  Volume(issue)/page/year: 15,355,1980

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 148 mg/kg
TOXIC EFFECTS :
   Blood - normocytic anemia
   Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 16,431,1982

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 137 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   RPTOAN Russian Pharmacology and Toxicology (English Translation).
   Translation of FATOAO.  (Euromed Pub., 33, Woodlands Rd., Surbiton, Surrey,
   UK)  V.30-    1967-  Volume(issue)/page/year: 36,240,1973

TYPE OF TEST            : LD50 - Lethal dose, 50 percent

TYPE OF TEST            : Unscheduled DNA synthesis
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 2 ug
REFERENCE :
   ECEBDI Experimental Cell Biology.  (S. Karger Pub., Inc., 79 Fifth Ave., New
   York, NY 10003) V.44-    1976-  Volume(issue)/page/year: 50,271,1982

TYPE OF TEST            : Phage inhibition capacity
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 100 ug/plate
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut

{h

TYPE OF TEST            : Sex chromosome loss and nondisjunction
ROUTE OF EXPOSURE       : Parenteral
TEST SYSTEM             : Insect - Drosophila melanogaster
DOSE/DURATION           : 19200 umol/L
REFERENCE :
   EVSRBT Environmental Science Research.  (Plenum Pub. Corp., 233 Spring St.,
   New York, NY 10013) V.1-    1972-  Volume(issue)/page/year: 24,175,1981

TYPE OF TEST            : Specific locus test
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Insect - Drosophila melanogaster
DOSE/DURATION           : 100 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 252,305,1991

TYPE OF TEST            : DNA damage
ROUTE OF EXPOSURE       : Intravenous
TEST SYSTEM             : Human
DOSE/DURATION           : 750 mg/kg
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   49,3452,1989

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Mold - Aspergillus nidulans
DOSE/DURATION           : 20 mg/plate
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 80,265,198

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE                    : 168 ug/kg
SEX/DURATION            : female 20 week(s) pr

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE                    : 980 mg/kg
SEX/DURATION            : female 2 week(s) pre-mating  - 33 week(s) after
                          conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - Central Nervous System
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
   Reproductive - Specific Developmental Abnormalities - gastrointestinal
   system
REFERENCE :
   TCMUD8 Teratogenesis, Carcinogenesis, and Mutagenesis.  (Alan R. Liss, Inc.,
   41 E. 11th St., New York, NY 10003)  V.1-    1980- Volume(issue)/page/year:
   13,139,1993

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE                    : 107 mg/kg
SEX/DURATION            : male 21 week(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - spermatogenesis (incl. genetic material,
   sperm morphology, motility, and count)
REFERENCE :
   LANCAO Lancet.  (7 Adam St., London WC2N 6AD, UK)  V.1-    1823-
   Volume(issue)/page/year: 2,156,1975

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Multiple routes
SPECIES OBSERVED        : Human - woman
DOSE                    : 382 mg/kg
SEX/DURATION            : female 1-39 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   JAMAAP JAMA, Journal of the American Me

Hazard statements
  • 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
Precautionary statements
  • 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。
  • 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。
  • 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。
  • 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。
  • 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+P312
  • P305+P351+P338
  • P307+P311
  • P308+P313
  • 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
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P330 Rinse mouth. 漱口
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....

其他信息

  • 烷化剂类抗肿瘤药:环磷酰胺 是一种最常用的烷化剂类抗肿瘤药，常温下为白色结晶或结晶性粉末（失去结晶水即液化），在室温中稳定。 溶于水，但溶解度不大。水溶液不稳定，故应在溶解后短期内使用。易溶于乙醇。1958年由Arnold和Bourseaux首次合 成，这种化合物及其衍生物的合成是基于之前的抗癌药物结构和作用而研制出来的。主要用于肿瘤免疫，进入人体内后 ，在肝微粒体酶催化下分解释出烷化作用很强的氯乙基磷酰胺(或称磷酰胺氮芥)，而对肿瘤细胞产生细胞毒作
  • 用法用量:环磷酰胺片：50mg 注射用环磷酰胺：（1）100mg（2）200mg 1.成人常用量口服每日按体重2~3mg/kg.静脉注射每次4mg/kg，每日或隔日一次。或每次600~1200mg，每7~10日一次。 2.小儿常用量口服每日按体重2~6mg/kg，静脉注射每次2—6mg/kg，每日或隔日一次。或每次10~15mg/kg，每周一次，以氯化钠注射液20ml稀释后缓慢注射。 （1）抗肿瘤：口服，一次50mg，一日3次；静注，一次每平方米400-600mg，每周一次，总量8g左右为一疗程。也可肌注，剂量同静注。动脉内注射，每次100-500mg，鞘内注射，每次50-100mg。 （2）免疫抑制：一日50-150mg，两次粉服，连服4-6周。静注，每次100-200mg，每日或隔日1次，连用4-6周。
  • Cyclophosphamide has been reported to be an anti-proliferative agent that regulates Bax and Bcl-2 expression. This compound also inhibits aldehyde dehydrogenase 1 through its degradation product acrolein.
  • 用途一:广谱抗肿瘤药，用于治疗白血病及其他肿瘤
  • MSDS 信息:Cyclophosphamide(50-18-0).msds
  • 适应症:适用于治疗恶性淋巴瘤、多发性骨髓瘤、淋巴细胞白血病、宫颈癌、前列腺癌、结肠癌、支气管癌、实体瘤如神经母细 胞瘤、卵巢癌、乳癌、各种肉瘤及肺癌等。也可用于类风湿关节炎、儿童肾病综合征以及自身免疫疾病的治疗。
  • Sigma Aldrich:50-18-0(sigmaaldrich)
  • 作用机制:环磷酰胺(简称CTX)为细胞周期非特异性细胞毒药物，但对G2期(DNA合成后期)作用更为强烈，主要的免疫抑制机制为： ①使T及B淋巴细胞绝对数目减少，早期对B淋巴细胞更明显。 ②明显抑制淋巴细胞对特异性抗原刺激后的母细胞转化。对有丝分裂素刺激后的抑制不如对特异性抗原。 ③抑制对新抗原的抗体反应及皮肤迟缓变态反应。 ④降低升高的免疫球蛋白水平，长期使用（几年）后有可能出现低丙球蛋白血症。 ⑤试管内选择性抑制B淋巴细胞功能，减少某些B淋巴细胞自发产生免疫球蛋白，和抑制一般的有丝分裂原受刺激后的免 疫球蛋白产生。 环磷酰胺在代谢前并无细胞毒作用，其活化必须依赖肝细胞微粒体酶系统中的细胞色素P450氧化形成4-羟基环磷酰胺， 开环后再变成活性很强的磷酰胺氮芥，从而发挥细胞毒作用。
  • MOL 文件:50-18-0.mol
  • 副作用:环磷酰胺治疗狼疮性肾炎目前已被临床上普遍接受，但是作为医生和病人，在治疗的过程中，要了解其有何副作用，从而尽量避免和减少它的发生，环磷酰胺主要副作用如下： 1，首次使用环磷酰胺治疗时，可能会产生较严重的胃肠道反应，如恶心、呕吐、食欲不振等，此时可用甲氧氯普胺(胃复安)、多潘立酮(吗丁啉)等胃动力药。 2，能抑制免疫细胞，又能抑制骨髓的造血功能，要定期化验血常规，看看有无影响。 3，国外报道，环磷酰胺应用后会引起出血性膀胱炎，而在国内，这类情况发生率较低，可以在治疗期间多饮水，冲淡该药在膀胱中的浓度。 4，能抑制卵巢功能，破坏卵巢中的卵泡，影响生育。所以在有要求生育的年轻病人中使用要慎重，如必须使用，则次数不能太多，以免生殖功能丧失。 5，在长期的应用中发现，环磷酰胺能抑制人体的免疫功能，同样也降低了人体防癌的能力，个别病人可产生继发性肿瘤，但是在国内还没有这方面的报道。一般认为该药诱发肿瘤的风险与剂量、疗程有关，采用低剂量、间歇疗法可降低肿瘤的发生率，一般使用不超过2年。

系列性分类

  1. Functional Group 官能团索引
  2. phosphoric acid amide

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