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Merck
CN

C2235

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
NACRES:
NA.32
PubChem Substance ID:
24278301
UNSPSC Code:
12352204
MDL number:
MFCD00869490

Key Documents

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Product Name

CB 1954, solid

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)

SMILES string

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

InChI key

WOCXQMCIOTUMJV-UHFFFAOYSA-N

assay

≥94% (HPLC)

form

solid

storage temp.

−20°C

Quality Level

200

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLCJ6707
SLCB5559
SLCB5348
SLBS3090V
SLBS0463V

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Andrew Christofferson et al.
Biochemical Society transactions, 37(Pt 2), 413-418 (2009-03-18)
NTR (nitroreductase NfsB from Escherichia coli) is a flavoprotein with broad substrate specificity, reducing nitroaromatics and quinones using either NADPH or NADH. One of its substrates is the prodrug CB1954 (5-[aziridin-1-yl]-2,4-dinitrobenzamide), which is converted into a cytotoxic agent; so NTR/CB1954
Thymopoiesis in mice depends on a Foxn1-positive thymic epithelial cell lineage
Corbeaux T, et al.
Proceedings of the National Academy of Sciences of the USA, 1-6 (2010)
Gareth A Prosser et al.
Biochemical pharmacology, 85(8), 1091-1103 (2013-02-13)
Two potentially complementary approaches to improve the anti-cancer strategy gene-directed enzyme prodrug therapy (GDEPT) are discovery of more efficient prodrug-activating enzymes, and development of more effective prodrugs. Here we demonstrate the utility of a flexible screening system based on the
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
Prashant Patel et al.
Molecular therapy : the journal of the American Society of Gene Therapy, 17(7), 1292-1299 (2009-04-16)
We report a phase I/II clinical trial in prostate cancer (PCa) using direct intraprostatic injection of a replication defective adenovirus vector (CTL102) encoding bacterial nitroreductase (NTR) in conjunction with systemic prodrug CB1954. One group of patients with localized PCa scheduled
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