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시클로포스파미드 구조식 이미지
카스 번호:
CY;ASTA;B 518;Clafen;Neosar;CB 4564;Endoxan;Enduxan;Genoxal;Mitoxan
포뮬러 무게:
MOL 파일:

시클로포스파미드 속성

물리적 상태
Soluble. 1-5 g/100 mL at 23 ºC
Stable, but light sensitive. Incompatible with oxidizing agents.
CAS 데이터베이스
50-18-0(CAS DataBase Reference)
2H-1,3,2-Oxazaphosphorin- 2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide(50-18-0)


안전지침서 22-24/25
유엔번호(UN No.) UN 1851
위험 등급 6.1(b)
포장분류 III
유해 물질 데이터 50-18-0(Hazardous Substances Data)

시클로포스파미드 MSDS


시클로포스파미드 C화학적 특성, 용도, 생산

화학적 성질

Endoxan is a white crystalline powder (monohydrate). It may be used or shipped in solution. Darkens on exposure to light. Odorless


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




ChEBI: A phosphorodiamide that is 1,3,2-oxazaphosphinan-2-amine 2-oxide substituted by two 2-chloroethyl groups at the amino nitrogen atom.


Cyclophosphamide (Cytoxan) is the most versatile and useful of the nitrogen mustards. Preclinical testing showed it to have a favorable therapeutic index and to possess the broadest spectrum of antitumor activity of all alkylating agents. As with the other nitrogen mustards, cyclophosphamide administration results in the formation of cross-links within DNA due to a reaction of the two chloroethyl moieties of cyclophosphamide with adjacent nucleotide bases. Cyclophosphamide must be activated metabolically by microsomal enzymes of the cytochrome P450 system before ionization of the chloride atoms and formation of the cyclic ethylenimmonium ion can occur. The metabolites phosphoramide mustard and acrolein are thought to be the ultimate active cytotoxic moiety derived from cyclophosphamide.


Cytoxan (Bristol-Myers Squibb); Neosar (Sicor).

일반 설명

Fine white crystalline powder. Odorless with a slightly bitter taste. Melting point 41-45°C. A 2% solution has pH of 4 to 6. Used medicinally as an antineoplastic agent.

일반 설명

Cyclophosphamide is available in 25- and 50-mg tabletsfor oral administration and 100-, 200-, 500-, 1,000-, and2,000-mg vials for IV use in the treatment of a wide varietyof cancers, including breast cancer, non-Hodgkin’s lymphoma,chronic lymphocytic leukemia, ovarian cancer, boneand soft tissue sarcoma, rhabdomyosarcoma, neuroblastoma,and Wilms tumor. Coadministration of mesna is recommended.The alkylating agent is cell cycle–nonspecific,and mechanisms of resistance are similar to those seen forother alkylating agents including decreased uptake and activationand increased inactivation by glutathione and oxidaseenzymes (aldehyde dehydrogenase and alcohol dehydrogenase)as well as increased DNA repair mechanisms. Theagent is well absorbed when given orally. Metabolism byCYP2B6 and 3A4/5 is required for activation of the agent,and metabolites are formed as a result of this activation bysubsequent reactions that are shown in Scheme 10.5. Themajor metabolite seen in plasma is the phosphoramide mustard,although there is a small amount of material (10%)arising from the dechloroethylation, which is primarily mediatedby 3A4/5. This metabolic pathway gives rise to asmall amount of chloroacetaldehyde, which is both neurotoxicand nephrotoxic. The parent compound and metabolitesare eliminated in the urine with an elimination half-lifeof 4 to 6 hours. Adverse effects include dose-limitingmyelosuppression, which normally presents as leucopenia.Bladder toxicity, which presents as hemorrhagic cystitis, isrelated to the formation of electrophilic species in the kidneyincluding acrolein and may be treated by administrationof mesna and increased water intake. Additionally, amenorrheamay be seen and sterility may be permanent. Othereffects include alopecia, cardiotoxicity, inappropriate secretionof antidiuretic hormone, and an increased risk ofsecondary cancers.

공기와 물의 반응

Water soluble.

반응 프로필

Cyclophosphamide is sensitive to exposure to light (darkens). Also sensitive to oxidation. Aqueous solutions may be kept for a few hours at room temperature, but hydrolysis occurs at temperatures above 86°F. Solutions in DMSO, 95% ethanol or acetone are stable for 24 hours under normal lab conditions. Incompatible with benzyl alcohol. Undergoes both acid and base hydrolysis at extreme pHs


Flash point data for Cyclophosphamide are not available; however, Cyclophosphamide is probably combustible.

Mechanism of action

Cyclophosphamide can be given orally, intramuscularly, or intravenously. The plasma half-life of intact cyclophosphamide is 6.5 hours.Only 10 to 15% of the circulating parent drug is protein bound, whereas 50% of the alkylating metabolites are bound to plasma proteins. Since cyclophosphamide and its metabolites are eliminated primarily by the kidneys, renal failure will greatly prolong their retention.
Cyclophosphamide has a wide spectrum of antitumor activity. In lymphomas, it is frequently used in combination with vincristine and prednisone (CVP [or COP] regimen) or as a substitute for mechlorethamine in the MOPP regimen (C-MOPP). High dosages of intravenously administered cyclophosphamide are often curative in Burkitt’s lymphoma, a childhood malignancy with a very fast growth rate.Oral daily dosages are useful for less aggressive tumors, such as nodular lymphomas, myeloma, and chronic leukemias.

Clinical Use

Cyclophosphamide is a component of CMF (cyclophosphamide, methotrexate, 5-fluorouracil) and other drug combinations used in the treatment of breast cancer. Cyclophosphamide in combination may produce complete remissions in some patients with ovarian cancer and oat cell (small cell) lung cancer. Other tumors in which beneficial results have been reported include non–oat cell lung cancers, various sarcomas, neuroblastoma, and carcinomas of the testes, cervix, and bladder. Cyclophosphamide also can be employed as an alternative to azathioprine in suppressing immunological rejection of transplant organs.

Safety Profile

Confirmed human carcinogen producing leukemia, Hodgkin's dsease, gastrointestinal and bladder tumors. Experimental carcinogenic, neoplas tigenic, and teratogenic data. A human poison by ingestion and many other routes. Human systemic effects: hdney changes (hepatic dysfunction), leukopenia (reduced white blood cell count), nausea and alopecia (loss of hair), liver changes, agranulocytosis. Human reproductive and teratogenic effects by multiple routes: spermatogenesis, testicular changes, epiddymis and sperm duct changes, menstrual cycle changes, fetal developmental abnormahties of the craniofacial area, musculoskeletal and cardiovascular systems. Experimental reproductive effects. Human mutation data reported. A powerful skin irritant. Used as an immunosuppressive agent in nonmalignant diseases. When heated to decomposition it emits hghly toxic fumes of PO,, NOx, and Cl-.

잠재적 노출

Exodan is used as an immunosuppressive agent in nonmalignant diseases; treatment of malignant lymphoma, multiple meyloma; leukemias, and other malignant diseases. Exodan has been tested as an insect chemosterilant and for use in the chemical shearing of sheep. Exodan is not produced in the United States.; manufactured in Germany and imported into the United States since1959. The FDA estimates that 200,000300,000 patients per year are treated with exodan. It is administered orally and through injection. The adult dosage is usually 15 mg/kg of body weight daily or 1015 mg/kg administered intravenous every 710 days

Veterinary Drugs and Treatments

In veterinary medicine, cyclophosphamide is used primarily in small animals (dogs and cats) in combination with other agents both as an antineoplastic agent (lymphomas, leukemias, carcinomas, and sarcomas) and as an immunosuppressant (SLE, ITP, IMHA, pemphigus, rheumatoid arthritis, proliferative urethritis, etc.). Its use in treating acute immune-mediated hemolytic anemia is controversial;there is some evidence that it does not add beneficial effects when used with prednisone.
Cyclophosphamide has been used as a chemical shearing agent in sheep.


Cyclophosphamide is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.

운송 방법

UN3464 Organophosphorus compound, solid, toxic, n.o.s, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN1851 Medicine, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials

비 호환성

Should be protected from exposure to temperatures above 30°C/86°F.

폐기물 처리

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal


Consumer Product Safety Commission (CPSC)
Any orally administered prescription drug for human use requires child-resistant packaging.
Environmental Protection Agency (EPA)
Comprehensive Environmental Response, Compensation, and Liability Act
Reportable quantity (RQ) = 10 lb.
Resource Conservation and Recovery Act
Listed Hazardous Waste: Waste code for which the listing is based wholly or partly on the presence of cyclophosphamide = U058.
Listed as a hazardous constituent of waste.
Food and Drug Administration (FDA)
Cyclophosphamide is a prescription drug subject to labeling and other requirements.

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