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C0768

Cyclophosphamide monohydrate

Name: Cyclophosphamide monohydrate
Brand: SIGMA

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Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₇H₁₅Cl₂N₂O₂P · H₂O

CAS Number:

6055-19-2

Molecular Weight:

279.10

Beilstein:

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

GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H340,H350,H360FD

Precautionary Statements

P202 - P264 - P280 - P301 + P310 - P405 - P501

Hazard Classifications

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Down-regulation of the Notch pathway mediated by a gamma-secretase inhibitor induces anti-tumour effects in mouse models of T-cell leukaemia.

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

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)

A tritherapy combination of inactivated allogeneic leukocytes infusion and cell vaccine with cyclophosphamide in a sequential regimen enhances antitumor immunity

Tang Y, et al.

Journal of the Chinese Medical Association : JCMA, 81(4), 316-323 (2018)

Cyclophosphamide

Ogino MH, et al.

JAK-STAT Pathway in Disease (2020)

Immunosuppressive effect of cyclophosphamide on white blood cells and lymphocyte subpopulations from peripheral blood of Balb/c mice

Huyan XH, et al.

International Immunopharmacology, 11(9), 1293-1297 (2011)

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Chromatograms

HPLC Analysis of Cyclophosphamide Enantiomers on Astec^® CHIROBIOTIC^® T

application for HPLC

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