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Merck

C0768

Cyclophosphamide monohydrate

97.0-103.0% (HPLC), Alkylating agent, powder

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
NACRES:
NA.77
PubChem Substance ID:
57653979
UNSPSC Code:
51112507
EC Number:
200-015-4
MDL number:
MFCD00149395
Beilstein/REAXYS Number:
4678992

Key Documents

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Product Name

Cyclophosphamide monohydrate, bulk package

InChI key

PWOQRKCAHTVFLB-UHFFFAOYSA-N

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

SMILES string

[H]O[H].ClCCN(CCCl)P1(=O)NCCCO1

assay

97.0-103.0% (HPLC)

form

powder

mp

49-51 °C (lit.)

storage temp.

2-8°C

Quality Level

200

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.
Cytotoxic nitrogen mustard derivative widely used in cancer chemotherapy. It cross-links DNA, causes strand breakage, and induces mutations.

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

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

WGK 3

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

C0768-1G: + C0768-25G: + C0768-10G: + C0768-VAR: + C0768-5G: + C0768-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD5120V
MKCN3646
MKCL2547
MKBX1822V
WXBD0289V

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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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