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39800-16-3,MFCD01710226
Catalog No.:AA00BXI9

39800-16-3 | 4-HYDROPEROXY CYCLOPHOSPHAMIDE

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1mg
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5mg
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$245.00   $171.00
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10mg
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25mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00BXI9
Chemical Name:
4-HYDROPEROXY CYCLOPHOSPHAMIDE
CAS Number:
39800-16-3
Molecular Formula:
C7H15Cl2N2O4P
Molecular Weight:
293.0848
MDL Number:
MFCD01710226
SMILES:
ClCCN(P1(=O)OCCC(N1)OO)CCCl
NSC Number:
181815
Properties
Properties
 
Form:
Solid  
MP:
81-84°C  

Computed Properties
 
Complexity:
253  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
6  
Undefined Atom Stereocenter Count:
2  
XLogP3:
0.3  

Literature

Title: Effects of four chemotherapeutic agents, bleomycin, etoposide, cisplatin, and cyclophosphamide, on DNA damage and telomeres in a mouse spermatogonial cell line.

Journal: Biology of reproduction 20140401

Title: Methylated chrysin reduced cell proliferation, but antagonized cytotoxicity of other anticancer drugs in acute lymphoblastic leukemia.

Journal: Anti-cancer drugs 20120401

Title: The enzymatic activity of human aldehyde dehydrogenases 1A2 and 2 (ALDH1A2 and ALDH2) is detected by Aldefluor, inhibited by diethylaminobenzaldehyde and has significant effects on cell proliferation and drug resistance.

Journal: Chemico-biological interactions 20120105

Title: Effects of exposure to a DNA damaging agent on the hypoxia inducible factors in organogenesis stage mouse limbs.

Journal: PloS one 20120101

Title: Teratogen responsive signaling pathways in organogenesis stage mouse limbs.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20090401

Title: Inhibition of human sperm respiration by 4-hydroperoxycyclophosphamide and protection by mesna and WR-1065.

Journal: Fertility and sterility 20090101

Title: The gene expression profiles of medulloblastoma cell lines resistant to preactivated cyclophosphamide.

Journal: Current cancer drug targets 20080501

Title: 4-hydroperoxy-cyclophosphamide mediates caspase-independent T-cell apoptosis involving oxidative stress-induced nuclear relocation of mitochondrial apoptogenic factors AIF and EndoG.

Journal: Cell death and differentiation 20080201

Title: Heterogeneity of aldehyde dehydrogenase expression in lung cancer cell lines is revealed by Aldefluor flow cytometry-based assay.

Journal: Cytometry. Part B, Clinical cytometry 20070701

Title: Cyclophosphamide-induced apoptosis in COV434 human granulosa cells involves oxidative stress and glutathione depletion.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20070701

Title: Cytotoxic effects of histone deacetylase inhibitor FK228 (depsipeptide, formally named FR901228) in combination with conventional anti-leukemia/lymphoma agents against human leukemia/lymphoma cell lines.

Journal: Investigational new drugs 20070201

Title: RNAi-mediated knockdown of aldehyde dehydrogenase class-1A1 and class-3A1 is specific and reveals that each contributes equally to the resistance against 4-hydroperoxycyclophosphamide.

Journal: Cancer chemotherapy and pharmacology 20070101

Title: Teratogen-induced activation of p53 in early postimplantation mouse embryos.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20070101

Title: Chemotherapy disrupts activity of translational regulatory proteins in bone marrow stromal cells.

Journal: Experimental hematology 20061101

Title: Design, synthesis, and biological evaluation of cyclic and acyclic nitrobenzylphosphoramide mustards for E. coli nitroreductase activation.

Journal: Journal of medicinal chemistry 20060713

Title: Characterizing the ovotoxicity of cyclophosphamide metabolites on cultured mouse ovaries.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20060401

Title: Cyclophosphamide enhances TNF-alpha-induced apoptotic cell death in murine vascular endothelial cell.

Journal: FEBS letters 20060306

Title: Predictive value of in vitro assessment of cytotoxic drug activity in advanced breast cancer.

Journal: Anti-cancer drugs 20050701

Title: Retinoic acid down-regulates aldehyde dehydrogenase and increases cytotoxicity of 4-hydroperoxycyclophosphamide and acetaldehyde.

Journal: The Journal of pharmacology and experimental therapeutics 20050101

Title: Oxidative DNA damage induced by a hydroperoxide derivative of cyclophosphamide.

Journal: Free radical biology & medicine 20040915

Title: Alterations in gene expression induced in day-9 mouse embryos exposed to hyperthermia (HS) or 4-hydroperoxycyclophosphamide (4CP): analysis using cDNA microarrays.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20040601

Title: Interleukin-12 enhances the sensitivity of human osteosarcoma cells to 4-hydroperoxycyclophosphamide by a mechanism involving the Fas/Fas-ligand pathway.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040115

Title: Teratogen-induced activation of caspase-6 and caspase-7 in early postimplantation mouse embryos.

Journal: Cell biology and toxicology 20030801

Title: 4-hydroperoxycyclophosphamide--purged peripheral blood stem cells for autologous transplantation in patients with acute myeloid leukemia.

Journal: Biology of blood and marrow transplantation : journal of the American Society for Blood and Marrow Transplantation 20030301

Title: Teratogen-induced activation of the mitochondrial apoptotic pathway in the yolk sac of day 9 mouse embryos.

Journal: Birth defects research. Part A, Clinical and molecular teratology 20030201

Title: Enhanced bystander cytotoxicity of P450 gene-directed enzyme prodrug therapy by expression of the antiapoptotic factor p35.

Journal: Cancer research 20021201

Title: Protracted low-dose effects on human endothelial cell proliferation and survival in vitro reveal a selective antiangiogenic window for various chemotherapeutic drugs.

Journal: Cancer research 20021201

Title: Novel competitive irreversible inhibitors of aldehyde dehydrogenase (ALDH1): restoration of chemosensitivity of L1210 cells overexpressing ALDH1 and induction of apoptosis in BAF(3) cells overexpressing bcl(2).

Journal: Biochemical pharmacology 20021015

Title: Kinetic analysis of the reactions of 4-hydroperoxycyclophosphamide and acrolein with glutathione, mesna, and WR-1065.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20020801

Title: Teratogen-induced activation of caspase-9 and the mitochondrial apoptotic pathway in early postimplantation mouse embryos.

Journal: Toxicology and applied pharmacology 20020601

Title: Autologous bone marrow transplantation with 4-hydroperoxycyclophosphamide purging for acute myeloid leukaemia beyond first remission: a 10-year experience.

Journal: British journal of haematology 20020601

Title: Purging in autologous hematopoietic stem cell transplantation using adenosine triphosphate (ATP) and 4-hydroperoxycyclophosphamide (4-HC).

Journal: Leukemia research 20020501

Title: Cellular mechanisms of cyclophosphamide resistance: model studies in human medulloblastoma cell lines.

Journal: Cancer treatment and research 20020101

Title: Expression of base excision, mismatch, and recombination repair genes in the organogenesis-stage rat conceptus and effects of exposure to a genotoxic teratogen, 4-hydroperoxycyclophosphamide.

Journal: Teratology 20011201

Title: DNA repair initiated in chronic lymphocytic leukemia lymphocytes by 4-hydroperoxycyclophosphamide is inhibited by fludarabine and clofarabine.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20011101

Title: L-buthionine sulfoximine potentiates the antitumor effect of 4-hydroperoxycyclophosphamide when administered locally in a rat glioma model.

Journal: Neurosurgery 20010201

Title: Generation of dual resistance to 4-hydroperoxycyclophosphamide and methotrexate by retroviral transfer of the human aldehyde dehydrogenase class 1 gene and a mutated dihydrofolate reductase gene.

Journal: Molecular therapy : the journal of the American Society of Gene Therapy 20010101

Title: Effect of O6-benzylguanine on alkylating agent-induced toxicity and mutagenicity. In Chinese hamster ovary cells expressing wild-type and mutant O6-alkylguanine-DNA alkyltransferases.

Journal: Cancer research 20001001

Title: De novo expression of transfected human class 1 aldehyde dehydrogenase (ALDH) causes resistance to oxazaphosphorine anti-cancer alkylating agents in hamster V79 cell lines. Elevated class 1 ALDH activity is closely correlated with reduction in DNA interstrand cross-linking and lethality.

Journal: The Journal of biological chemistry 19960517

Title: Immediate hypersensitivity reaction to cyclophosphamide.

Journal: Arthritis and rheumatism 19940701

Title: Intrathecal 4-hydroperoxycyclophosphamide: neurotoxicity, cerebrospinal fluid pharmacokinetics, and antitumor activity in a rabbit model of VX2 leptomeningeal carcinomatosis.

Journal: Cancer research 19921115

Title: Studies on the urotoxicity of oxazaphosphorine cytostatics and its prevention--I. Experimental studies on the urotoxicity of alkylating compounds.

Journal: European journal of cancer 19810601

Title: 4-hydroperoxy-cyclophosphamide mediates caspase-independent T-cell apoptosis involving oxidative stress-induced nuclear relocation of mitochondrial apoptogenic factors AIF and EndoG

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