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Key Documents

C2235

Sigma-Aldrich

CB 1954

solid

Synonym(s):

5-(1-Aziridinyl)-2,4-dinitrobenzamide, 5-(Aziridin-1-yl)-2,4-dinitrobenzamide

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About This Item

CAS Number:
21919-05-1
MDL number:
MFCD00869490
UNSPSC Code:
12352204
PubChem Substance ID:
24278301
NACRES:
NA.32

Assay

≥94% (HPLC)

Quality Level

200

form

solid

storage temp.

−20°C

SMILES string

NC(=O)c1cc(N2CC2)c(cc1[N+]([O-])=O)[N+]([O-])=O

InChI

1S/C9H8N4O5/c10-9(14)5-3-7(11-1-2-11)8(13(17)18)4-6(5)12(15)16/h3-4H,1-2H2,(H2,10,14)

InChI key

WOCXQMCIOTUMJV-UHFFFAOYSA-N

Application

CB 1954 has been used in drug-induced ablation studies.

Biochem/physiol Actions

CB 1954 is an anticancer prodrug used in gene therapy research; activated by NAD(P)H quinone oxidoreductase 2.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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S O Vass et al.
British journal of cancer, 100(12), 1903-1911 (2009-05-21)
Prodrug activation gene therapy is a developing approach to cancer treatment, whereby prodrug-activating enzymes are expressed in tumour cells. After administration of a non-toxic prodrug, its conversion to cytotoxic metabolites directly kills tumour cells expressing the activating enzyme, whereas the
Mark R Middleton et al.
Science translational medicine, 2(40), 40ra50-40ra50 (2010-07-16)
DNA-damaging agents are widely used in cancer treatment despite their lack of tumor specificity. Human NQO2 (quinone oxidoreductase-2) is an atypical oxidoreductase because no endogenous electron donor has been identified to date. The enzyme converts CB1954 [5-(aziridin-1-yl)-2,4-dinitrobenzamide], in the presence
David Onion et al.
Human gene therapy, 20(11), 1249-1258 (2009-07-22)
We have completed a phase I/II suicide gene therapy clinical trial in patients with prostate cancer, using an E1/E3-deleted replication-deficient adenovirus (CTL102) encoding the bacterial nitroreductase enzyme in combination with prodrug CB1954. This study has provided an opportunity to monitor
Alexia Chandor et al.
Chemical research in toxicology, 21(4), 836-843 (2008-03-29)
Nitric oxide synthases (NOSs) are flavohemeproteins that catalyze the oxidation of L-arginine to L-citrulline with formation of the signaling molecule nitric oxide (NO). In addition to their fundamental role in NO biosynthesis, NOSs are also involved in the formation of
David Jarrom et al.
Biochemistry, 48(32), 7665-7672 (2009-07-08)
The enzyme nitroreductase, NfsB, from Escherichia coli has entered clinical trials for cancer gene therapy with the prodrug CB1954 [5-(aziridin-1-yl)-2,4-dinitrobenzamide]. However, CB1954 is a poor substrate for the enzyme. Previously we made several NfsB mutants that show better activity with
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