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C0768 Sigma-Aldrich

Cyclophosphamide monohydrate

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Synonym: 2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide, Cytoxan

  • CAS Number 6055-19-2

  • Empirical Formula (Hill Notation) C7H15Cl2N2O2P · H2O

  • Molecular Weight 279.10

  •  Beilstein/REAXYS Number 4678992

  •  EC Number 200-015-4

  •  MDL number MFCD00149395

  •  PubChem Substance ID 57653979

  •  NACRES NA.77



Related Categories ALDH1A, Apoptosis Reagents, Apoptosis and Cell Cycle, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
assay   97.0-103.0% (HPLC)
mp   49-51 °C (lit.)
storage temp.   2-8°C
SMILES string   [H]O[H].ClCCN(CCCl)P1(=O)NCCCO1
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
Gene Information   human ... ALDH1A1(216), ALDH1B1(219)


General description

Cyclophosphamide (CYC) is a cytotoxic alkylating agent. It is activated by the cytochrome P-450 enzyme system in the liver. It has immunomodulatory functionality and inhibits humoral and cellular immunity.


Cyclophosphamide monohydrate has been used:
• to test its antitumor effect on TC-1 tumor cells
• as a component of multidrug solution for isolation of resistant human burkitt lymphoma cell line
• in testing antitumor immunity in mouse tumor cell lines


1, 5, 10, 25 g in glass bottle

Biochem/physiol Actions

Cyclophosphamide is a cytotoxic nitrogen mustard derivative widely used in cancer chemotherapy. It cross-links DNA, causes strand breakage, and induces mutations. Its clinical activity is associated with a decrease in aldehyde dehydrogenase 1 (ALDH1) activity.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

GHS06  GHS06
Signal word 
Hazard statements 
Precautionary statements 
UN 3464 6.1 / PGIII
WGK Germany 


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles


ABC Transporters and Cancer Drug Resistance

Chemotherapy is the treatment of choice against many types of cancer. However, over time chemotherapeutic drugs can become less effective due to the development of resistance that involves a group of...
BioFiles 2007, 2.4, 7.
Keywords: Absorption, Cancer, Clinical, Cloning, Combinatorial synthesis, Diseases, Enzymology, Gene expression, Genetic, Immunology, Pharmaceutical, Reductions, Transfection

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete. The expansion of the carcinogenesi...
Vicki Caligur
BioFiles 2008, 3.5, 18.
Keywords: Acetylations, Adhesion, Alkylations, Apoptosis, Biofiles, Cancer, Carcinogens, Cell division, Cell proliferation, Cell signaling, DNA microarrays, Drug discovery, Environmental, Epigenetics, Events, Gene expression, Genetic, Hormones, Metabolism, Methylations, Microarray Analysis, Mutagens, PAGE, Recombination, Reductions, Sequences, Transcription, Type, transformation

Discover Bioactive Small Molecules for Apoptosis

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Clinical, Diseases, Ligands, Neurodegenerative Diseases

Discover Bioactive Small Molecules for Cell Cycle Research

In proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during t...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Cell division, Cell proliferation, DNA replication, Diseases, Genetic

Peer-Reviewed Papers


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