CYCLOPHOSPHAMIDE

Synonyms. Cyclophosphamide; Ciclophosphamide; Cyclophosphamidum; Cyklofosfamid; (RS)-Cyclophosphamide; Ciclofosfamida; 1-Bis(2-chloroethyl)amino-1-oxo-2-aza- 5-oxaphosphoridin; 2-(Bis(2-chloroethyl) amino)-2H-1,3,2-oxazaphosphorine 2-oxide; 2-(Bis(2-chloroethyl) amino) tetrahydro -2H- 1,3,2-oxazophosphorine 2-oxide; Endoxanal; 4-Hydroxy- cyclophosphan- mamo phosphatide; Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester; Genoxal; N,N-Bis(2-chloroethyl)-N',O-propylenephosphoric acid ester diamide; N,N-Bis(beta-chloroethyl)-N',O- trimethylenephosphoric acid ester diamide; Zyklophosphamid;

CYCLOPHOSPHAMIDE

Click for original image

 

PRODUCT IDENTIFICATION

CAS RN

50-18-0 (anhydrous), 6055-19-2 (monohydrate)

EINECS RN

200-015-4

FORMULA

 C7H15Cl2N2O2P

MOLE WEIGHT

261.09

H.S CODE

 2934.99.9000

SMILES

 N([P@@]1(NCCCO1)=O)(CCCl)CCCl

CLASSIFICATION

Imidazotetrazine alkylating agent, Antineoplastic agent,Defleecing agent

EXTRA NOTES

 Precursor of an alkylating nitrogen mustard antineoplastic and immunosuppressive agent that must be activated in the liver to form the active aldophosphamide. It has been used in the treatment of lymphoma and leukemia. Its side effect, alopecia, has been used for defleecing sheep. Cyclophosphamide may also cause sterility, birth defects, mutations, and cancer (Mesh).
Overall Carcinogenic Evaluation: Group 1
Other RN: 60007-95-6, 75526-90-8

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

white to off-white crystalline powder

MELTING POINT

51 ~ 52 C

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

40 g/l

SOLVENT SOLUBILITY Sparingly soluble in ether and acetone. Soluble in alcohol, benzene, ethylene glycol, chloroform, dioxane.

VAPOR DENSITY

 

log P(octanol-water)

 0.63

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pK

15.29

REFRACTIVE INDEX

 

FLASH POINT

 

 
STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents.

POLYMERIZATION

Has not been reported

NFPA RATINGS

Health: 2, Flammability: 0, Reactivity: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Cyclophosphamide

Google Scholar Search - Cyclophosphamide

Drug Information Portal (U.S. National Library of Medicine) - Cyclophosphamide

PubChem Compound Summary - Cyclophosphamide

Drug Bank -  Cyclophosphamide

KEGG (Kyoto Encyclopedia of Genes and Genomes) - Cyclophosphamide

http://www.ebi.ac.uk/ - Cyclophosphamide

http://www.ncbi.nlm.nih.gov/ - Cyclophosphamide

http://toxnet.nlm.nih.gov/
Hazardous Substances Data Bank - Cyclophosphamide

http://www.vcu.edu/
Cyclophosphamide (Cytoxan®, CPH, CAS No. 50-18-0) is an antineoplastic compound that is chemically related to nitrogen mustard. Cyclophosphamide is an odorless, fine white to off-white crystalline powder that is soluble in water and ethanol (NTP, 2005). Cyclophosphamide is used clinically to treat a wide range of cancers including malignant lymphomas, myeloma, leukemia, mycosis fungoides, neuroblastoma, adenocarcinoma, retinoblastoma, and breast carcinoma (Bristol-Myers Squibb Co, 2003). Other clinical uses for CPH include immunosuppressive therapy following organ transplants or as a treatment for autoimmune disorders such as rheumatoid arthritis, Wegener’s granulomatosis, and nephritic syndrome in children (Chabner et al., 2001). Metabolism of CPH takes place in the liver and undergoes metabolic activation by cytochrome P450 isoenzyme 2B (Chabner et al., 2006). The major circulating metabolite of CPH, 4-Hydroxycyclophosphamide, is in equilibrium with its tautomer, aldophosphamide, which is spontaneously broken down to produce phosphoramide mustard and acrolein (Zhang et al., 2005). Phosphoramide mustard is responsible for anti-tumor effects, while acrolein is responsible for the hemorrhagic cystitis observed during CPH therapy (Chabner et al., 2006).....

 

SALES SPECIFICATION

APPEARANCE

white to off-white crystalline powder

ASSAY

98.5% min

MELTING POINT

51 ~ 52 C
IMPURITY

1.0% max (total), 0.5% max (individual)

LOSS ON DRYING

1.0% max

HEAVY METALS

20ppm max
RESIDUE ON IGNITION

0.1% max

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

3464

HAZARD CLASS

 6.1
PACKING GROUP III

 

SAFETY INFORMATION

HAZARD OVERVIEW

May cause respiratory irritation. May cause genetic defects. Toxic if swallowed. Causes serious eye irritation. May cause cancer. Causes skin irritation. May damage the unborn child

GHS

  

SIGNAL WORD

Danger

PICTOGRAMS

HAZARD STATEMENTS

H335-H340-H301-H319-H350-H315-H360D

P STATEMENTS

P301 + P310-P201-P308 + P313-P261-P302+ P352-P280-P305 + P351 + P338

EC DIRECTIVES

 

HAZARD CODES

T

RISK PHRASES

45-46-61-25-36/37/38

SAFETY PHRASES

 53-26-37/39-45

 

PACKING

Preserve in light-resistant and well-closed containers