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Key Documents

C0768

Sigma-Aldrich

Cyclophosphamide monohydrate

bulk package

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C7H15Cl2N2O2P · H2O
Número CAS:
Peso molecular:
279.10
Beilstein:
4678992
Número CE:
Número MDL:
Código UNSPSC:
51112507
ID de substância PubChem:
NACRES:
NA.77

Ensaio

97.0-103.0% (HPLC)

forma

powder

pf

49-51 °C (lit.)

temperatura de armazenamento

2-8°C

cadeia de caracteres 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

chave InChI

PWOQRKCAHTVFLB-UHFFFAOYSA-N

Informações sobre genes

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Descrição geral

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.

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Pictogramas

Skull and crossbonesHealth hazard

Palavra indicadora

Danger

Frases de perigo

Classificações de perigo

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

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

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


Certificados de análise (COA)

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Sigma-Aldrich

C0253

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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)

Artigos

We presents an article on ABC Transporters and Cancer Drug Resistance

Conteúdo relacionado

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

Chromatograms

application for HPLC

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