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C0768

Sigma-Aldrich

Cyclophosphamide monohydrate

bulk package

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C7H15Cl2N2O2P · H2O
Numéro CAS:
6055-19-2
Poids moléculaire :
279.10
Numéro Beilstein :
4678992
Numéro CE :
200-015-4
Numéro MDL:
MFCD00149395
Code UNSPSC :
51112507
ID de substance PubChem :
57653979
Nomenclature NACRES :
NA.77

Pureté

97.0-103.0% (HPLC)

Forme

powder

Pf

49-51 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

[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

Clé InChI

PWOQRKCAHTVFLB-UHFFFAOYSA-N

Informations sur le gène

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

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Description générale

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H301,H340,H350,H360FD

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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