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Imexon

CAS No.:
59643-91-3
Catalog Number:
AG00EIRB
Molecular Formula:
C4H5N3O
Molecular Weight:
111.1020
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Product Description
Catalog Number:
AG00EIRB
Chemical Name:
Imexon
CAS Number:
59643-91-3
Molecular Formula:
C4H5N3O
Molecular Weight:
111.1020
MDL Number:
MFCD08435947
IUPAC Name:
4-amino-1,3-diazabicyclo[3.1.0]hex-3-en-2-one
InChI:
InChI=1S/C4H5N3O/c5-3-2-1-7(2)4(8)6-3/h2H,1H2,(H2,5,6,8)
InChI Key:
BIXBBIPTYBJTRY-UHFFFAOYSA-N
SMILES:
NC1=NC(=O)N2C1C2
EC Number:
261-838-2
Properties
Complexity:
186  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
111.043g/mol
Formal Charge:
0
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
111.104g/mol
Monoisotopic Mass:
111.043g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
58.5A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.4  
Literature
Title Journal
Anti-tumor activity and mechanism of action for a cyanoaziridine-derivative, AMP423. Cancer chemotherapy and pharmacology 20120401
Imexon induces an oxidative endoplasmic reticulum stress response in pancreatic cancer cells. Molecular cancer research : MCR 20120301
Chemistry and pharmacology of imexon and related cyanoaziridines. Current medicinal chemistry 20120101
Interaction of dacarbazine and imexon, in vitro and in vivo, in human A375 melanoma cells. Anticancer research 20110901
Imexon enhances gemcitabine cytotoxicity by inhibition of ribonucleotide reductase. Cancer chemotherapy and pharmacology 20110101
A phase I trial of imexon, a pro-oxidant, in combination with docetaxel for the treatment of patients with advanced breast, non-small cell lung and prostate cancer. Investigational new drugs 20101001
A phase 1-2 study of imexon plus dacarbazine in patients with unresectable metastatic melanoma. Cancer 20100801
Combined phase I/II study of imexon (AOP99.0001) for treatment of relapsed or refractory multiple myeloma. Anti-cancer drugs 20100801
A phase I study of imexon plus gemcitabine as first-line therapy for advanced pancreatic cancer. Cancer chemotherapy and pharmacology 20100701
Redox-directed cancer therapeutics: molecular mechanisms and opportunities. Antioxidants & redox signaling 20091201
Imexon augments sensitivity of human lymphoma cells to ionizing radiation: in vitro experimental study. Anticancer research 20091101
Inhibition of protein synthesis by imexon reduces HIF-1alpha expression in normoxic and hypoxic pancreatic cancer cells. Investigational new drugs 20090201
New analytical techniques to facilitate preformulation screening in propellant systems. International journal of pharmaceutics 20070801
The antitumor agent imexon activates antioxidant gene expression: evidence for an oxidative stress response. Clinical cancer research : an official journal of the American Association for Cancer Research 20070601
Imexon-based combination chemotherapy in A375 human melanoma and RPMI 8226 human myeloma cell lines. Cancer chemotherapy and pharmacology 20070501
Phase I trial of imexon in patients with advanced malignancy. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20070501
Preclinical antitumor activity, pharmacokinetics and pharmacodynamics of imexon in mice. Anti-cancer drugs 20061101
Preformulation studies on imexon. Drug development and industrial pharmacy 20060701
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Oxidative stress and apoptosis: a new treatment paradigm in cancer. Frontiers in bioscience : a journal and virtual library 20060101
Correlates of imexon sensitivity in human multiple myeloma cell lines. Leukemia & lymphoma 20060101
Targeting mitochondria emerges as therapeutic strategy. Journal of the National Cancer Institute 20051221
Rob Ashley of AmpliMed discusses the discovery and development of Imexon. Interview by Steve Carney. Drug discovery today 20051015
Compatibility and stability of Imexon in infusion devices and its in vitro biocompatibility. Anti-cancer drugs 20050801
LC-UV method development and validation for the investigational anticancer agent imexon and identification of its degradation products. Journal of pharmaceutical and biomedical analysis 20050715
Pharmaceutical development of a lyophilised dosage form for the investigational anticancer agent Imexon using dimethyl sulfoxide as solubilising and stabilising agent. Journal of pharmaceutical sciences 20050501
Induction of apoptosis and cell cycle arrest by imexon in human pancreatic cancer cell lines. International journal of gastrointestinal cancer 20050101
Imexon-induced apoptosis in multiple myeloma tumor cells is caspase-8 dependent. Clinical cancer research : an official journal of the American Association for Cancer Research 20040215
Chemical basis for the biological activity of imexon and related cyanoaziridines. Journal of medicinal chemistry 20040101
Cytotoxic effects of B lymphocytes mediated by reactive oxygen species. Current pharmaceutical design 20040101
Imexon activates an intrinsic apoptosis pathway in RPMI8226 myeloma cells. Anti-cancer drugs 20021101
Molecular and cellular characterization of imexon-resistant RPMI8226/I myeloma cells. Molecular cancer therapeutics 20020101
Induction of mitochondrial changes in myeloma cells by imexon. Blood 20010601
Induction of oxidative stress and apoptosis in myeloma cells by the aziridine-containing agent imexon. Biochemical pharmacology 20000915
Antiproliferative and antitumor activity of the 2-cyanoaziridine compound imexon on tumor cell lines and fresh tumor cells in vitro. Journal of the National Cancer Institute 19920819
Antiviral efficacy of Imexon in the Rauscher murine retrovirus AIDS model. Immunopharmacology and immunotoxicology 19900101
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