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C0768

Sigma-Aldrich

Cyclophosphamide monohydrate

bulk package

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Synonym(s):
2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide, Cytoxan
Empirical Formula (Hill Notation):
C7H15Cl2N2O2P · H2O
CAS Number:
Molecular Weight:
279.10
Beilstein/REAXYS Number:
4678992
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
PHR1404239785C7397
Cyclophosphamide monohydrate bulk package

C0768

Cyclophosphamide monohydrate

Cyclophosphamide Pharmaceutical Secondary Standard; Certified Reference Material

PHR1404

Cyclophosphamide

Cyclophosphamide Monohydrate A widely used anti-neoplastic agent that also displays immunosuppressant properties.

239785

Cyclophosphamide Monohydrate

Cyclophosphamide monohydrate ISOPAC®

C7397

Cyclophosphamide monohydrate

assay

97.0-103.0% (HPLC)

assay

-

assay

≥98% (HPLC)

assay

97.0-103.0% (HPLC)

Quality Level

200

Quality Level

300

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

mp

49-51 °C (lit.)

mp

49-51 °C (lit.)

mp

-

mp

49-51 °C (lit.)

Gene Information

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

Gene Information

-

Gene Information

-

Gene Information

-

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.

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

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


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Biochemical and biophysical research communications, 488(1), 182-188 (2017)
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
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Articles

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Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Chromatograms

application for HPLC

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