Home Other Building Blocks 4-HYDROPEROXY CYCLOPHOSPHAMIDE

4-HYDROPEROXY CYCLOPHOSPHAMIDE

CAS No.:
39800-16-3
Catalog Number:
AG00BXL1
Molecular Formula:
C7H15Cl2N2O4P
Molecular Weight:
293.0848
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$160
- +
5mg
≥95%
1 week
United States
$250
- +
10mg
≥95%
1 week
United States
$437
- +
25mg
≥95%
1 week
United States
$862
- +
Product Description
Catalog Number:
AG00BXL1
Chemical Name:
4-HYDROPEROXY CYCLOPHOSPHAMIDE
CAS Number:
39800-16-3
Molecular Formula:
C7H15Cl2N2O4P
Molecular Weight:
293.0848
MDL Number:
MFCD01710226
IUPAC Name:
N,N-bis(2-chloroethyl)-4-hydroperoxy-2-oxo-1,3,2λ5-oxazaphosphinan-2-amine
InChI:
InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(13)10-7(15-12)1-6-14-16/h7,12H,1-6H2,(H,10,13)
InChI Key:
VPAWVRUHMJVRHU-UHFFFAOYSA-N
SMILES:
ClCCN(P1(=O)OCCC(N1)OO)CCCl
NSC Number:
181815
Properties
Complexity:
253  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
292.015g/mol
Formal Charge:
0
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
293.081g/mol
Monoisotopic Mass:
292.015g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
71A^2
Undefined Atom Stereocenter Count:
2  
Undefined Bond Stereocenter Count:
0
XLogP3:
0.3  
Literature
Title Journal
Effects of four chemotherapeutic agents, bleomycin, etoposide, cisplatin, and cyclophosphamide, on DNA damage and telomeres in a mouse spermatogonial cell line. Biology of reproduction 20140401
Methylated chrysin reduced cell proliferation, but antagonized cytotoxicity of other anticancer drugs in acute lymphoblastic leukemia. Anti-cancer drugs 20120401
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. Chemico-biological interactions 20120105
Effects of exposure to a DNA damaging agent on the hypoxia inducible factors in organogenesis stage mouse limbs. PloS one 20120101
Teratogen responsive signaling pathways in organogenesis stage mouse limbs. Reproductive toxicology (Elmsford, N.Y.) 20090401
Inhibition of human sperm respiration by 4-hydroperoxycyclophosphamide and protection by mesna and WR-1065. Fertility and sterility 20090101
The gene expression profiles of medulloblastoma cell lines resistant to preactivated cyclophosphamide. Current cancer drug targets 20080501
4-hydroperoxy-cyclophosphamide mediates caspase-independent T-cell apoptosis involving oxidative stress-induced nuclear relocation of mitochondrial apoptogenic factors AIF and EndoG. Cell death and differentiation 20080201
Heterogeneity of aldehyde dehydrogenase expression in lung cancer cell lines is revealed by Aldefluor flow cytometry-based assay. Cytometry. Part B, Clinical cytometry 20070701
Cyclophosphamide-induced apoptosis in COV434 human granulosa cells involves oxidative stress and glutathione depletion. Toxicological sciences : an official journal of the Society of Toxicology 20070701
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. Investigational new drugs 20070201
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. Cancer chemotherapy and pharmacology 20070101
Teratogen-induced activation of p53 in early postimplantation mouse embryos. Toxicological sciences : an official journal of the Society of Toxicology 20070101
Chemotherapy disrupts activity of translational regulatory proteins in bone marrow stromal cells. Experimental hematology 20061101
Design, synthesis, and biological evaluation of cyclic and acyclic nitrobenzylphosphoramide mustards for E. coli nitroreductase activation. Journal of medicinal chemistry 20060713
Characterizing the ovotoxicity of cyclophosphamide metabolites on cultured mouse ovaries. Toxicological sciences : an official journal of the Society of Toxicology 20060401
Cyclophosphamide enhances TNF-alpha-induced apoptotic cell death in murine vascular endothelial cell. FEBS letters 20060306
Predictive value of in vitro assessment of cytotoxic drug activity in advanced breast cancer. Anti-cancer drugs 20050701
Retinoic acid down-regulates aldehyde dehydrogenase and increases cytotoxicity of 4-hydroperoxycyclophosphamide and acetaldehyde. The Journal of pharmacology and experimental therapeutics 20050101
Oxidative DNA damage induced by a hydroperoxide derivative of cyclophosphamide. Free radical biology & medicine 20040915
Alterations in gene expression induced in day-9 mouse embryos exposed to hyperthermia (HS) or 4-hydroperoxycyclophosphamide (4CP): analysis using cDNA microarrays. Toxicological sciences : an official journal of the Society of Toxicology 20040601
Interleukin-12 enhances the sensitivity of human osteosarcoma cells to 4-hydroperoxycyclophosphamide by a mechanism involving the Fas/Fas-ligand pathway. Clinical cancer research : an official journal of the American Association for Cancer Research 20040115
Teratogen-induced activation of caspase-6 and caspase-7 in early postimplantation mouse embryos. Cell biology and toxicology 20030801
4-hydroperoxycyclophosphamide--purged peripheral blood stem cells for autologous transplantation in patients with acute myeloid leukemia. Biology of blood and marrow transplantation : journal of the American Society for Blood and Marrow Transplantation 20030301
Teratogen-induced activation of the mitochondrial apoptotic pathway in the yolk sac of day 9 mouse embryos. Birth defects research. Part A, Clinical and molecular teratology 20030201
Enhanced bystander cytotoxicity of P450 gene-directed enzyme prodrug therapy by expression of the antiapoptotic factor p35. Cancer research 20021201
Protracted low-dose effects on human endothelial cell proliferation and survival in vitro reveal a selective antiangiogenic window for various chemotherapeutic drugs. Cancer research 20021201
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). Biochemical pharmacology 20021015
Kinetic analysis of the reactions of 4-hydroperoxycyclophosphamide and acrolein with glutathione, mesna, and WR-1065. Drug metabolism and disposition: the biological fate of chemicals 20020801
Teratogen-induced activation of caspase-9 and the mitochondrial apoptotic pathway in early postimplantation mouse embryos. Toxicology and applied pharmacology 20020601
Autologous bone marrow transplantation with 4-hydroperoxycyclophosphamide purging for acute myeloid leukaemia beyond first remission: a 10-year experience. British journal of haematology 20020601
Purging in autologous hematopoietic stem cell transplantation using adenosine triphosphate (ATP) and 4-hydroperoxycyclophosphamide (4-HC). Leukemia research 20020501
Cellular mechanisms of cyclophosphamide resistance: model studies in human medulloblastoma cell lines. Cancer treatment and research 20020101
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. Teratology 20011201
DNA repair initiated in chronic lymphocytic leukemia lymphocytes by 4-hydroperoxycyclophosphamide is inhibited by fludarabine and clofarabine. Clinical cancer research : an official journal of the American Association for Cancer Research 20011101
L-buthionine sulfoximine potentiates the antitumor effect of 4-hydroperoxycyclophosphamide when administered locally in a rat glioma model. Neurosurgery 20010201
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. Molecular therapy : the journal of the American Society of Gene Therapy 20010101
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. Cancer research 20001001
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. The Journal of biological chemistry 19960517
Immediate hypersensitivity reaction to cyclophosphamide. Arthritis and rheumatism 19940701
Intrathecal 4-hydroperoxycyclophosphamide: neurotoxicity, cerebrospinal fluid pharmacokinetics, and antitumor activity in a rabbit model of VX2 leptomeningeal carcinomatosis. Cancer research 19921115
Studies on the urotoxicity of oxazaphosphorine cytostatics and its prevention--I. Experimental studies on the urotoxicity of alkylating compounds. European journal of cancer 19810601
Properties