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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:
51101500
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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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
M F Sarosdy
European urology, 31 Suppl 1, 20-26 (1997-01-01)
Bropirimine has been shown to have activity against carcinoma in situ (CIS) of the bladder in a previous phase-I trial. A review of three completed clinical trials as well as ongoing studies is presented to provide a current update. Details
S M Vroegop et al.
International journal of immunopharmacology, 21(10), 647-662 (2003-03-01)
We showed previously that a 5-halo-6-phenyl-pyrimidinone, bropirimine (PNU-54461), inhibited progression of severe experimental autoimmune encephalomyelitis (EAE), an animal model of human multiple sclerosis. In the work presented here, we examined the activity of a group of chemically-related bropirimine analogues. First
C Y Hsu et al.
Journal of chromatography. A, 762(1-2), 243-249 (1997-02-21)
A rapid and simple high-performance liquid chromatography (HPLC) method incorporating automated solid-phase extraction (SPE) is described for the determination of bropirimine, 2-amino-5-bromo-6-phenyl-4(3H)-pyrimidinone, in plasma samples from various species. Using an automated sample processor, plasma samples were loaded onto C18 SPE
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