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)
Molecular Formula | C10H8BrN3O |
Molecular Weight | 266.094 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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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Pyrimidinones. 1. 2-Amino-5-halo-6-aryl-4(3H)-pyrimidinones. Interferon-inducing antiviral agents. | 1985 Dec |
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Protection from carcinogen-induced murine bladder carcinoma by interferons and an oral interferon-inducing pyrimidinone, bropirimine. | 1990 Feb 15 |
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Antiviral and immunomodulating inhibitors of experimentally-induced Punta Toro virus infections. | 1994 Oct |
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Lack of interaction between bropirimine and 5-fluorouracil on human dihydropyrimidine dehydrogenase. | 2001 Jan |
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Characterization of bropirimine O-glucuronidation in human liver microsomes. | 2003 Oct |
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Intravesical hyperthermia and mitomycin-C for carcinoma in situ of the urinary bladder: experience of the European Synergo working party. | 2009 Jun |
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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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:46:19 UTC 2023
by
admin
on
Fri Dec 15 15:46:19 UTC 2023
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Record UNII |
J57CTF25XJ
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Record Status |
Validated (UNII)
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Record Version |
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C2139
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m594
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SUB05928MIG
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C033560
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BROPIRIMINE
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CHEMBL37387
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149027
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C1024
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5903
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3689
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