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Merck
CN

29875

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

Key Documents

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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

WGK 3

ppe

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

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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
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)
Z-H Niu et al.
European review for medical and pharmacological sciences, 17(10), 1337-1344 (2013-06-07)
Preoperative chemotherapy is often used in patients with locally advanced breast cancer. However, commonly used clinical and pathological parameters are poor predictors of response to this type of therapy. The secreted form of the CLU protein (sCLU) is a glycosylated
Ulrich Specks et al.
The New England journal of medicine, 369(5), 417-427 (2013-08-02)
The 18-month efficacy of a single course of rituximab as compared with conventional immunosuppression with cyclophosphamide followed by azathioprine in patients with severe (organ-threatening) antineutrophil cytoplasmic antibody (ANCA)-associated vasculitis is unknown. In a multicenter, randomized, double-blind, double-dummy, noninferiority trial, we
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