U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of BROPIRIMINE

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)

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
5-substituted 2-amino-6-phenyl-4(3H)-pyrimidinones. Antiviral- and interferon-inducing agents.
1980 Mar
Pyrimidinones. 1. 2-Amino-5-halo-6-aryl-4(3H)-pyrimidinones. Interferon-inducing antiviral agents.
1985 Dec
Antiviral and immunomodulating inhibitors of experimentally-induced Punta Toro virus infections.
1994 Oct
The limits of bacillus Calmette-Guerin for carcinoma in situ of the bladder.
2001 Mar
Current state of immunotherapy for bladder cancer.
2004 Dec
Superficial bladder cancer therapy.
2004 Jun 28
Current and new strategies in immunotherapy for superficial bladder cancer.
2004 Sep
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
The expression and functions of toll-like receptors in atherosclerosis.
2010
Patents

Sample Use Guides

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
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.
Name Type Language
BROPIRIMINE
INN   JAN   MART.   MI   USAN  
USAN   INN  
Official Name English
bropirimine [INN]
Common Name English
BROPIRIMINE [MI]
Common Name English
U-54461
Code English
BROPIRIMINE [JAN]
Common Name English
NSC-149027
Code English
U-54,461
Code English
BROPIRIMINE [MART.]
Common Name English
BROPIRIMINE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2139
Created by admin on Fri Dec 15 15:46:19 GMT 2023 , Edited by admin on Fri Dec 15 15:46:19 GMT 2023
Code System Code Type Description
MERCK INDEX
m594
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PRIMARY Merck Index
EVMPD
SUB05928MIG
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PRIMARY
EPA CompTox
DTXSID5046803
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PRIMARY
FDA UNII
J57CTF25XJ
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PRIMARY
PUBCHEM
135413497
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PRIMARY
SMS_ID
100000088682
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PRIMARY
DRUG BANK
DB04168
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PRIMARY
MESH
C033560
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PRIMARY
WIKIPEDIA
BROPIRIMINE
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PRIMARY
CAS
56741-95-8
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PRIMARY
USAN
S-39
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PRIMARY
ChEMBL
CHEMBL37387
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PRIMARY
NSC
149027
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PRIMARY
NCI_THESAURUS
C1024
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PRIMARY
INN
5903
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PRIMARY
DRUG CENTRAL
3689
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PRIMARY