BROPIRIMINE

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 Search

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
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
Toll-like receptor 7 12 Target ID: CHEMBL5936 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26399683	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Bladder cancer 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16301114	Primary	Phase II 1132	Unknown Approved Use Unknown
Renal cell carcinoma 31 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9020948	Primary	Phase II 1132	Unknown Approved Use Unknown
malignant lymphoma 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9020948	Primary	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
5-substituted 2-amino-6-phenyl-4(3H)-pyrimidinones. Antiviral- and interferon-inducing agents.	1980 Mar	7365739
Antiviral and other bioactivities of pyrimidinones.	1985	2428070
Pyrimidinones. 1. 2-Amino-5-halo-6-aryl-4(3H)-pyrimidinones. Interferon-inducing antiviral agents.	1985 Dec	2999405
Antiviral and immunomodulating inhibitors of experimentally-induced Punta Toro virus infections.	1994 Oct	7847873
Immunotherapy for bladder cancer.	2001 Feb	12084297
Lack of interaction between bropirimine and 5-fluorouracil on human dihydropyrimidine dehydrogenase.	2001 Jan	11334264
The limits of bacillus Calmette-Guerin for carcinoma in situ of the bladder.	2001 Mar	11176460
In vitro antitumor activity of bropirimine against urinary bladder tumor cells.	2002 May-Jun	12168852
Characterization of bropirimine O-glucuronidation in human liver microsomes.	2003 Oct	14555337
Superficial bladder cancer therapy.	2004 Jun 28	15349563
Intravesical hyperthermia and mitomycin-C for carcinoma in situ of the urinary bladder: experience of the European Synergo working party.	2009 Jun	19234857
The expression and functions of toll-like receptors in atherosclerosis.	2010	20652007

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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