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29875

Sigma-Aldrich

Cyclophosphamide monohydrate

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
Beilstein/REAXYS Number:
4678992
EC Number:
200-015-4
MDL number:
MFCD00149395
UNSPSC Code:
12352200
PubChem Substance ID:
329753395

mp

49-51 °C (lit.)

solubility

H2O: 0.1 g/mL, clear, colorless

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

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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.

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_germany

WGK 3

ppe

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

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Jin-Gang Hou et al.
Biochemical and biophysical research communications, 436(1), 104-109 (2013-06-04)
Chemotherapy frequently results in neurocognitive deficits that include impaired learning and memory. Thus, it is important to prevent or ameliorate the persistence of cognitive impairment. Compound K was employed to examine the ameliorating effect on chronic treatment with cyclophosphamide. Eight
G Pugnet et al.
Clinical and experimental rheumatology, 31(1 Suppl 75), S62-S64 (2013-07-24)
Progressive multifocal encephalopathy (PML) is a rare demyelinating disorder targeting the central nervous system and resulting from JC virus reactivation. PML occurs in patients immunocompromised because of haematological malignancies, HIV infection or treatment with cytotoxic drugs. Herein, we describe PML
Parotitis as the presenting symptom of Wegener's granulomatosis: case report and meta-analysis.
Ilan Green et al.
The Israel Medical Association journal : IMAJ, 15(3), 188-192 (2013-05-15)
Jennifer L Guerriero et al.
Cancer research, 68(23), 9595-9600 (2008-12-03)
Dysregulation of apoptosis is associated with the development of human cancer and resistance to anticancer therapy. The ultimate goal of cancer treatment is to selectively induce cancer cell death and overcome drug resistance. A deeper understanding of how a given
Sherene Loi et al.
Journal of the National Cancer Institute, 105(13), 960-967 (2013-06-07)
Certain somatic alterations in breast cancer can define prognosis and response to therapy. This study investigated the frequencies, prognostic effects, and predictive effects of known cancer somatic mutations using a randomized, adjuvant, phase III clinical trial dataset. The FinHER trial
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