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SML0218

Sigma-Aldrich

Bropirimine

≥98% (HPLC)

Synonym(s):

2-amino-5-bromo-6-phenyl-4(3H)-pyrimidinone, NSC 149027, PNU 54461, U 54461, U 54461S

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About This Item

Empirical Formula (Hill Notation):
C10H8BrN3O
CAS Number:
56741-95-8
Molecular Weight:
266.09
MDL number:
MFCD01689128
UNSPSC Code:
41116107
PubChem Substance ID:
329825238
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: ≥5 mg/mL (warm DMSO)

storage temp.

room temp

SMILES string

NC1=NC(=O)C(Br)=C(N1)c2ccccc2

InChI

1S/C10H8BrN3O/c11-7-8(6-4-2-1-3-5-6)13-10(12)14-9(7)15/h1-5H,(H3,12,13,14,15)

InChI key

CIUUIPMOFZIWIZ-UHFFFAOYSA-N

Application

Bropirimine, an immunostimulating agent and toll like receptor (TLR7) agonist, is used in comparison with other TLR7 agonists such as imiquimod, R-848, loxoribine in interferon cell signaling research. Bropirimine may be used in experimental autoimmune encephalomyelitis (EAE) and bladder cancer research.

Biochem/physiol Actions

Bropirimine is an immunostimulating agent. The compound induces production of α and β interferons and enhances NK cell function. Bropirimine has antiproliferative effects in cancer cell lines and tumor growth in in vivo models.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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U O Nseyo et al.
Seminars in surgical oncology, 13(5), 342-349 (1997-09-01)
Intravesical therapy has been used in the management of superficial transitional cell carcinoma (TCC) of the urinary bladder (i.e., Ta, Tl, and carcinoma in situ) with specific objectives which include treating existing/residual tumor, preventing recurrence of tumor, preventing disease progression
Masa Bosnjak et al.
The Journal of membrane biology, 251(2), 179-185 (2017-02-17)
Gene electrotransfer upregulate DNA pattern recognition receptors or DNA sensors, which are part of the innate immune system. In this study, we tested if addition of the cocktail of innate immune system inhibitors to the cells during gene electrotransfer (GET)
W P Witjes et al.
European urology, 36(6), 576-581 (1999-11-24)
This European phase III clinical trial was part of an intercontinental study which was closed prematurely by the sponsor. The study was designed to compare the effects of oral bropirimine with intravesical BCG, the current standard treatment in patients with
G Lievano et al.
Methods and findings in experimental and clinical pharmacology, 19(4), 261-267 (1997-05-01)
The role of bropirimine in prostate cancer remains unexplored. To address the efficacy of this immune modulator as neoadjuvant therapy we utilized the orthotopic placement of the Dunning AT-3 tumor. 2.4-2.6 x 10(6) Dunning AT-3 cells were injected into the
M A Wynalda et al.
Drug metabolism and disposition: the biological fate of chemicals, 26(10), 1048-1051 (1998-10-08)
Bropirimine (2-amino-5-bromo-6-phenyl-4-pyrimidinone) is a member of a class of antineoplastic agents known as aryl pyrimidinones. In human liver microsomal incubations, bropirimine oxidative metabolism is characterized by the formation of three metabolites. Mass spectrometric analysis of the incubation mixture revealed three
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