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C0768

Sigma-Aldrich

Cyclophosphamide monohydrate

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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

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

Signal Word

Danger

Hazard Statements

H301,H340,H350,H360FD

Hazard Classifications

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

Storage Class Code

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

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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Cyclophosphamide and cancer: golden anniversary
Emadi A, et al.
Nature Reviews. Clinical Oncology, 6(11), 638-638 (2009)
Cyclophosphamide pharmacokinetics and dose requirements in patients with renal insufficiency
Haubitz M, et al.
Kidney International, 61(4), 1495-1501 (2002)
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)
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)
Metronomic cyclophosphamide activation of anti-tumor immunity: tumor model, mouse host, and drug schedule dependence of gene responses and their upstream regulators
Wu J, et al.
BMC Cancer, 16(1), 623-623 (2016)
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Chromatograms

application for HPLC

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