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C0768

Sigma-Aldrich

Cyclophosphamide monohydrate

bulk package

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C7H15Cl2N2O2P · H2O
Número de CAS:
6055-19-2
Peso molecular:
279.10
Beilstein/REAXYS Number:
4678992
EC Number:
200-015-4
MDL number:
MFCD00149395
UNSPSC Code:
51112507
PubChem Substance ID:
57653979
NACRES:
NA.77

Quality Level

200

assay

97.0-103.0% (HPLC)

form

powder

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

InChI key

PWOQRKCAHTVFLB-UHFFFAOYSA-N

Gene Information

human ... ALDH1A1(216) , ALDH1B1(219)

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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 exhibits anti-cancer and immunosuppressant activities. In the body, cyclophosphamide is converted by the liver to an active alkylating 4-hydroxycyclophosphamide metabolite, thereby showing its anti-neoplastic effects.

Application

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

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.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Carc. 1B - Muta. 1B - Repr. 1A

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Cyclophosphamide pharmacokinetics and dose requirements in patients with renal insufficiency
Haubitz M, et al.
Kidney International, 61(4), 1495-1501 (2002)
Vered Domankevich et al.
Frontiers in oncology, 10, 990-990 (2020-08-09)
Diffusing alpha-emitting radiation therapy (DaRT) employs intratumoral Ra-224-coated seeds that efficiently destroy solid tumors by slowly releasing alpha-emitting atoms inside the tumor. In immunogenic tumor models, DaRT was shown to activate systemic antitumor immunity. Agonists of the membrane-bound toll-like receptors
Cyclophosphamide and cancer: golden anniversary
Emadi A, et al.
Nature Reviews. Clinical Oncology, 6(11), 638-638 (2009)
STAT3 mediates multidrug resistance of Burkitt lymphoma cells by promoting antioxidant feedback
Zeng R, et al.
Biochemical and biophysical research communications, 488(1), 182-188 (2017)
J Tammam et al.
British journal of pharmacology, 158(5), 1183-1195 (2009-09-25)
gamma-Secretase inhibitors (GSIs) block NOTCH receptor cleavage and pathway activation and have been under clinical evaluation for the treatment of malignancies such as T-cell acute lymphoblastic leukaemia (T-ALL). The ability of GSIs to decrease T-ALL cell viability in vitro is
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Chromatograms

application for HPLC

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