Cyclophosphamide

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Cat.No. 4091 - Cyclophosphamide | C7H15Cl2N2O2P | CAS No. 50-18-0
Description: Alkylating agent; chemotherapeutic
Chemical Name: 2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
Purity: ≥99% (HPLC)
Datasheet
Citations
Literature
Pathways

Biological Activity

Nitrogen mustard alkylating agent and prodrug. Phosphoramide mustard (active metabolite) forms DNA cross-links leading to cell death. Inhibits aldehyde dehydrogenase 1 (ALDH1) through its degradation product acrolein. Chemotherapeutic for the treatment of breast cancer; regulates Bax and Bcl-2 expression when administered with etoposide (Cat. No. 1226) in breast cancer cell lines.

Technical Data

M. Wt 261.09
Formula C7H15Cl2N2O2P
Storage Store at -20°C
Purity ≥99% (HPLC)
CAS Number 50-18-0
PubChem ID 2907
InChI Key CMSMOCZEIVJLDB-UHFFFAOYSA-N
Smiles O=P1(N(CCCl)CCCl)OCCCN1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 26.11 100
water 26.11 100

Preparing Stock Solutions

The following data is based on the product molecular weight 261.09. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.83 mL 19.15 mL 38.3 mL
5 mM 0.77 mL 3.83 mL 7.66 mL
10 mM 0.38 mL 1.92 mL 3.83 mL
50 mM 0.08 mL 0.38 mL 0.77 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Gibson et al (1999) Regulation of BAX and BCL-2 expression in breast cancer cells by chemotherapy. Breast Cancer Research and Treatment 55 107 PMID: 10481938

Hengstler et al (1992) DNA strand breaks and DNA cross-links in peripheral mononuclear blood cells of ovarian cancer patients during chemotherapy with cyclophosphamide/carboplatin. Cancer Res. 15 52 PMID:

Ren et al (1999) Inhibition of human aldehyde dehydrogenase 1 by the 4-hydroxycyclophosphamide degradation product acrolein. Drug Metab.Disp. 27 133 PMID:


If you know of a relevant reference for Cyclophosphamide, please let us know.

Keywords: chemotherapeutics cross-links alkylates DNA cytotoxic inhibits inhibitors aldehyde dehydrogenase 1 ALDH1 Apoptosis Inducers

Citations for Cyclophosphamide

Citations are publications that use Tocris products.

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Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Programmed Cell Death

Programmed Cell Death Poster

There are two currently recognized forms of programmed cell death: apoptosis and necroptosis. This poster summarizes the signaling pathways involved in apoptosis, necroptosis and cell survival following death receptor activation, and highlights the influence of the molecular switch, cFLIP, on cell fate.

Pathways for Cyclophosphamide

Apoptosis

Apoptosis Signaling Pathway

Apoptosis is a physiological process for cell death that is critical during aging and development. It may also be referred to as cell 'suicide'. Apoptosis can be triggered by events both inside and outside of the cell.

Protocols

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