Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H8BrN3O |
Molecular Weight | 266.094 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(C2=CC=CC=C2)=C(Br)C(=O)N1
InChI
InChIKey=CIUUIPMOFZIWIZ-UHFFFAOYSA-N
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)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/9076483Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16301114 | https://www.ncbi.nlm.nih.gov/pubmed/9020948 | https://www.ncbi.nlm.nih.gov/pubmed/26399683
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9076483
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16301114 | https://www.ncbi.nlm.nih.gov/pubmed/9020948 | https://www.ncbi.nlm.nih.gov/pubmed/26399683
Bropirimine, an immunostimulating agent, and toll-like receptor (TLR7) agonist, with anti-cancer and antiviral properties. Bropirimine may be used in experimental autoimmune encephalomyelitis (EAE) and bladder cancer research. 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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL5936 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26399683 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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5-substituted 2-amino-6-phenyl-4(3H)-pyrimidinones. Antiviral- and interferon-inducing agents. | 1980 Mar |
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Pyrimidinones. 1. 2-Amino-5-halo-6-aryl-4(3H)-pyrimidinones. Interferon-inducing antiviral agents. | 1985 Dec |
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Antiviral and immunomodulating inhibitors of experimentally-induced Punta Toro virus infections. | 1994 Oct |
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The limits of bacillus Calmette-Guerin for carcinoma in situ of the bladder. | 2001 Mar |
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Current state of immunotherapy for bladder cancer. | 2004 Dec |
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Superficial bladder cancer therapy. | 2004 Jun 28 |
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Current and new strategies in immunotherapy for superficial bladder cancer. | 2004 Sep |
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A phase II clinical trial of oral bropirimine in combination with intravesical bacillus Calmette-Guérin for carcinoma in situ of the bladder: a Southwest Oncology Group Study. | 2005 Nov-Dec |
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The expression and functions of toll-like receptors in atherosclerosis. | 2010 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16301114
Initially, daily dosage was 4.5 grams in three divided doses of 1.5 gram every two hours. A dose reduction to 3.0 gm. per day was made after recognition of possible cardiac toxicity in other studies that were ongoing simultaneously. Bropirimine was taken for 12 consecutive weeks
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26399683
Bone marrow cells (BMCs) were collected from femora and tibiae of 6-week-old male C57BL/6 mice, and cultured for 6 h in alphaMEM containing 10% fetal bovine serum (FBS) in Petri dishes. Mouse BMCs (1 x 105 cells/well) and mouse osteoblastic UAMS- 32 cells were co-cultured in 96-well plates for 4 days in aMEM supplemented with 10% FBS in the absence or presence of 1alpha,25(OH)2D3 (10 nmol/L), and various concentrations of bropirimine. Medium was replaced with fresh containing the same supplemental agents on day 3. As described above, TRAP activity staining was employed to evaluate osteoclast differentiation.
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C2139
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ACTIVE MOIETY