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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
Empirical Formula (Hill Notation):
C7H15Cl2N2O2P · H2O
CAS Number:
Molecular Weight:
279.10
Beilstein:
4678992
EC Number:
MDL number:
PubChem Substance ID:
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

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This Item
PHR1404C7397239785
Cyclophosphamide Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1404

Cyclophosphamide

form

powder

form

-

form

powder

form

solid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

200

Quality Level

300

Quality Level

100

Quality Level

100

mp

49-51 °C (lit.)

mp

49-51 °C (lit.)

mp

49-51 °C (lit.)

mp

-

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

Signal Word

Danger

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

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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)
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
Cyclophosphamide and cancer: golden anniversary
Emadi A, et al.
Nature Reviews. Clinical Oncology, 6(11), 638-638 (2009)
Vered Domankevich et al.
Frontiers in oncology, 10, 990-990 (2020-08-09)
Diffusing alpha-emitting radiation therapy (DaRT) employs intratumoral Ra-224-coated seeds that efficiently destroy solid tumors by slowly releasing alpha-emitting atoms inside the tumor. In immunogenic tumor models, DaRT was shown to activate systemic antitumor immunity. Agonists of the membrane-bound toll-like receptors
Cyclophosphamide pharmacokinetics and dose requirements in patients with renal insufficiency
Haubitz M, et al.
Kidney International, 61(4), 1495-1501 (2002)

Articles

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

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Chromatograms

application for HPLC

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