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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

Molecular Formula C10H8BrN3O
Molecular Weight 266.094
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Doses

AEs

PubMed

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.
Substance Class Chemical
Record UNII
J57CTF25XJ
Record Status Validated (UNII)
Record Version