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Merck
CN

SML0218

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:
Molecular Weight:
266.09
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
41116107
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
Storage condition:
desiccated
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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)

SMILES string

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

InChI key

CIUUIPMOFZIWIZ-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: ≥5 mg/mL (warm DMSO)

storage temp.

room temp

Quality Level

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 immunostimulant, anti-tumor agent
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

signalword

Warning

hcodes

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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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
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
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
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)
M Echezarreta-López et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 9(4), 381-386 (2000-02-09)
Bropirimine (ABPP) is an orally active immunomodulator that increases endogenous alpha-interferon and other cytokines used clinically against carcinoma in situ of the bladder. The oral absorption of ABPP is poor because its low solubility in water. The purpose of this

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