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Alkylating agent class antitumor medicine Mechanism Indications Usage and Dosage Side Effects Uses

CAS No.50-18-0
Chemical Name:Cyclophosphamide
Synonyms:CY;ASTA;B 518;Clafen;Neosar;CB 4564;Endoxan;Enduxan;Genoxal;Mitoxan
Molecular Formula:C7H15Cl2N2O2P
Formula Weight:261.085961
MOL File:50-18-0.mol
Cyclophosphamide Property
Melting point : 41-45°C
Water Solubility : Soluble. 1-5 g/100 mL at 23 ºC
Stability:: Stable, but light sensitive. Incompatible with oxidizing agents.
CAS DataBase Reference: 50-18-0(CAS DataBase Reference)
NIST Chemistry Reference: 2-[Bis(2-chloroethylamino)]-tetrahydro-2h-1,3,2-oxazaphosphorine-2-oxide(50-18-0)
EPA Substance Registry System: 2H-1,3,2-Oxazaphosphorin- 2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide(50-18-0)
Safety Statements : 22-24/25
RIDADR : UN 1851
HazardClass : 6.1(b)
PackingGroup : III
Hazardous Substances Data: 50-18-0(Hazardous Substances Data)

Cyclophosphamide Chemical Properties,Usage,Production

Alkylating agent class antitumor medicine
Cyclophosphamide is one of the most commonly used alkylating antineoplastic agents. It is white crystal or crystalline powder (loss of crystal water is liquefaction) at room temperature. It is stable at room temperature. Cyclophosphamide is dissolved in water but the solubility is a little low. Its aqueous solution is unstable. So it should be used within a short period after dissolution. It is also soluble in ethanol. In 1958, cyclophosphamide was first synthesized by the Arnold and Bourseaux. The synthesis of such compounds and derivatives are based on the previous structure and role of anticarcinogen. Cyclophosphamide is mainly used for tumor immunity. After entering the body, cyclophosphamide, catalyzed by the liver microsomal enzyme, will decompose and release chloroethyl phosphoramide (or phosphoramide mustard) that has strong alkylation. It has cytotoxic effects on tumor cells. And it can significantly inhibit a variety of tumors. In recent years, it has been demonstrated to have a variety of immunosuppressive effects and treatment of autoimmune diseases. It has made significant effect.
The above information is edited by the Chemicalbook Ge Qian.
Cyclophosphamide (CTX for short) is cell cycle non-specific cytotoxic drugs. But its effect in G2 period (DNA synthesis late) is more intense. The main mechanism of immunosuppression are as follows:
1. Decrease the absolute number of T and B lymphocytes. Its effect on B lymphocytes is more obvious in the early time.
2. Inhibit lymphocyte from specific antigen stimulation mother after conversion. Inhibition of mitogen stimulation is not as specific antigen.
3. Inhibit slow allergic reaction of new antigen-antibody reaction and skin.
4. Reduce elevated immunoglobulin levels. After long-term use (several years), hypogammaglobulinemia may occur.
5. Selectively inhibit B lymphocytes in vitro. Reduce certain B lymphocytes to spontaneously generate immunoglobulins, and inhibit the production of the general mitogen stimulated immunoglobulin.
Cyclophosphamide has no cytotoxicity before metabolism. Its activity must rely on that cytochrome P450 of hepatocyte microsomal enzyme system to oxidize to 4-hydroxy cyclophosphamide. The ring is opened to become highly active phosphoramide mustard. Then it can show cytotoxic effect.
Cyclophosphamide can be used in the treatment of malignant lymphoma, multiple myeloma, lymphocytic leukemia, cervical cancer, prostate cancer, colon cancer, bronchial cancer, solid tumors such as neuroblastoma cell tumors, ovarian cancer, breast cancer, lung cancer and a variety of sarcoma. It can also be used to treat rheumatoid arthritis, nephrotic syndrome in children and autoimmune diseases.
Usage and Dosage
Cyclophosphamide tablets: 50mg.
Cyclophosphamide for Injection: (1) 100mg (2) 200mg
1. Oral daily dosage of adults is according to the weight of 2~3mg/kg. The dosage of intravenous injection 4mg/kg every day or every other day at a time, or 600 ~1200mg for one time and once every 7 to 10 days.
2. Oral daily dosage of children is according to the weight of 2~6mg/kg. The dosage of intravenous injection 2~6mg/kg every day or every other day at a time. Or 20ml sodium chloride injection can be slowly injected after diluted every week.
(1) Antineoplastic: Oral, 50mg one time, three times a day; mainline, 400-600mg every centiare, once a week, the total 8g about a course of treatment. It also can be used in intramuscular injection and its dosage is same for mainline. The dosage of intra-arterial injection is 100-500mg every time. The dosage of intrathecal injection is 50-100mg every time.
(2) Immune suppression: 50-150mg every day, taking powder for two times. The dosage of intravenous injection is 100-500mg every day or every other day. It should be used for 4-6 consecutive weeks.
Side Effects
Cyclophosphamide used for the treatment of lupus nephritis has been widely accepted in clinical practice. But as a doctor and patient, one should understand its side effects in the treatment process to avoid and reduce the occurrence. The major side effects of cyclophosphamide are as follows:
1. When cyclophosphamide is first used during treatment, one may produce serious gastrointestinal reactions, such as nausea, vomiting, loss of appetite, etc. At this time metoclopramide (metoclopramide), domperidone (domperidone) and other gastric motility drugs are available.
2. It can not only suppress immune cells, but also inhibit the bone marrow hematopoietic function. Regular blood tests should be taken to see whether it impacts.
3. According to foreign reports, cyclophosphamide applications can cause hemorrhagic cystitis. But the incidence of such cases is low. More water should be drinked during the treatment to dilute the concentration of the drug in the bladder.
4. It can inhibit ovarian function and destroy ovarian follicles to affect fertility. So the use in young patients requiring fertility should be cautious. If it must be used, the times can’t be too much to cause the loss of reproductive function.
5. According to long-term applications, cyclophosphamide can inhibit the body's immune function, and reduce the body's ability to prevent cancer. Individual patients may have secondary tumors. But there are no reports in this regard at home. It is generally believed that it is related to its risks associated with the drug-induced tumor dose and treatment. The use of low-dose and intermittent therapy can reduce the incidence of cancer. It can generally be used for no more than 2 years.
Broad-spectrum antineoplastic agents. Cyclophosphamide can be used in the treatment of leukemia and other cancers.
Chemical Properties
white crystalline powder
ChEBI: A phosphorodiamide that is 1,3,2-oxazaphosphinan-2-amine 2-oxide substituted by two 2-chloroethyl groups at the amino nitrogen atom.
General Description
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.
Air & Water Reactions
Water soluble.
Reactivity Profile
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
Fire Hazard
Flash point data for Cyclophosphamide are not available; however, Cyclophosphamide is probably combustible.
Cyclophosphamide Preparation Products And Raw materials
Raw materials
Preparation Products
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50-18-0(Cyclophosphamide)Related Search:
2H-1,3,2-Oxazaphosphorine, tetrahydro-2-(bis(2-chloroethyl)amino)-5-ch loro-, 2-oxide, (Z)- 4-S-(Propionic acid)sulfidocyclophosphamide 5,5-dimethylcyclophosphamide CYCLOPHOSPHAMIDE,MONOHYDRATE,USP,CYCLOPHOSPHAMIDE 1-HYDRATE,CYCLOPHOSPHAMIDE MONOHYDRATE, 98+%,cyclophosphamide isopac,Cyclophosphamide sterile,CYCLOPHOSPHAMIDE(HYDRATED),cyclophosphamide,CTX,Cyclophosphamide monohydrate, 97+%,CYCLOPHOSPHAMIDE HYDRATE,CYCLOPHOSPHAMIDE MONOHYDRATE 4-methylcyclophosphamide Mafosfamide trofosfamide 4-(S-Ethanol)-sulfido-cyclophosphamide Cyclophosphamide Iron oxide NITRIC OXIDE Tris Base ETHYLENE OXIDE ALTRENOGEST NITROUS OXIDE 3-Aminophenol (Diethoxymethyl)diphenylphosphine oxide Glycine
(Bis(chloro-2-ethyl)amino)-2-tetrahydro-3,4,5,6-oxazaphosphorine-1,3,2-oxide-2 hydrate 2-(Bis(2-chloroethyl)amino)-2H-1,3,2-oxazaphosphorine 2-oxide 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide 2-H-1,3,2-Oxazaphosphorinane 2H-1,3,2-Oxazaphosphorine, 2-(bis(2-chloroethyl)amino)tetrahydro-,2-oxide 2H-1,3,2-Oxazaphosphorine, 2-(bis(2-chloroethyl)amino)tetrahydro-,2-oxide, monohydrate ASTA Asta B 518 B 518 Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester CB 4564 Clafen Claphene CY Cyclophosphamid Cyclophosphamidum Cyclophosphan Cyclophosphane Cyclophosphoramide Cyclostin Cyklofosfamid Cytophosphan Endoxan Endoxan R Endoxana Endoxanal Endoxan-Asta Endoxane Enduxan Genoxal Mitoxan N,N-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide N,N-Bis(2-chloroethyl)-N',O-propylenephosphoric acid ester diamide N,N-Bis-(beta-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid N,N-Bis(beta-chloroethyl)-N',O-trimethylenephosphoric acid ester diamide N,N-Di(2-chloroethyl)-N,O-propylene-phosphoric acid ester diamide NCI-C04900 Neosar NSC 26271 Phosphorodiamidic acid, N,N-bis(2-chloroethyl)-N'-(3-hydroxypropyl)-, intramol. ester Rcra waste number U058 Semdoxan Sendoxan Senduxan SK 20501 Zyklophosphamid 50-18-0 2-(bis(2-chloroethyl)amino)-1,3,2-oxazaphosphorinane 2-oxide 2H-1,3,2-Oxazaphosphosphorin-2-amine, N,N-bis(2-chloroethyl) tetrahydro-, 2-oxide 1-(Bis(2-chloroethyl)amino)-1-oxo-2-aza-5-oxaphosphoridine 2-(Di(2-chloroethyl)amino)-1-oxa-3-aza-2-phosphacyclohexane 2-oxide Cyclophosphamide 2-Bis(2-chloroethyl)aminotetrahydro-2H-1,3,2-oxazophosphorine-2-oxide Aids002314 Aids-002314 Clafen(CyclophosphaMide) CyclophosphaMide COS 2-(Bis(2-chloroethyl)amino)-2H-1,3,2-oxazaphosphorine 2-oxid
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