Bropirimine

Names

[ Name ]:
Bropirimine

[Synonym ]:
4(1H)-pyrimidinone, 2-amino-5-bromo-6-phenyl-
2-Amino-5-bromo-6-phenyl-4(1H)-pyrimidinone
2-Amino-5-bromo-6-phenylpyrimidin-4(1H)-one
4(3H)-pyrimidinone, 2-amino-5-bromo-6-phenyl-
Bropirimine
2-Amino-5-bromo-6-phenylpyrimidin-4-ol
4-Pyrimidinol, 2-amino-5-bromo-6-phenyl-
ABPP
2-amino-5-bromo-6-phenyl-1H-pyrimidin-4-one

Biological Activity

[Description]:

Bropirimine is a synthetic agonist for toll-like receptor 7 (TLR7). Bropirimine inhibits differentiation of osteoclast precursor cells into osteoclasts via TLR7-mediated production of IFN-β. Bropirimine is an orally active immunomodulator that has demonstrated anticancer activity in transitional cell carcinoma in situ (CIS) in both the bladder and upper urinary tract[1][2].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Toll-like Receptor (TLR)

Research Areas >> Cancer

[References]

[1]. Suzuki H, et al. Bropirimine inhibits osteoclast differentiation through production of interferon-β. Biochem Biophys Res Commun. 2015;467(1):146‐151.

[2]. Sarosdy MF, et al. Oral bropirimine immunotherapy of bladder carcinoma in situ after prior intravesical bacille Calmette-Guérin. Urology. 1998;51(2):226‐231.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
473.2±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₀H₈BrN₃O

[ Molecular Weight ]:
266.094

[ Flash Point ]:
240.0±31.5 °C

[ Exact Mass ]:
264.985077

[ PSA ]:
72.03000

[ LogP ]:
1.90

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.696

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UW7351300

CHEMICAL NAME :: 4(1H)-Pyrimidinone, 2-amino-5-bromo-6-phenyl-

CAS REGISTRY NUMBER :: 56741-95-8

BEILSTEIN REFERENCE NO. :: 0651807

LAST UPDATED :: 199703

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C10-H8-Br-N3-O

MOLECULAR WEIGHT :: 266.12

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >3200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 910 mg/kg/52W-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - hematuria Kidney, Ureter, Bladder - other changes Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 7280 mg/kg/52W-I

TOXIC EFFECTS :: Liver - other changes Kidney, Ureter, Bladder - other changes Related to Chronic Data - changes in prostate weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2900 mg/kg

SEX/DURATION :: female 15-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1450 mg/kg

SEX/DURATION :: female 15-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 200 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 200 mg/kg

SEX/DURATION :: female 5 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 300 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 252,221,1991

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H361

[ Precautionary Statements ]:
P281

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
UW7351300

[ HS Code ]:
2933599090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2933599090

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

CMV specific cytokine release assay in whole blood is optimized by combining synthetic CMV peptides and toll like receptor agonists.

J. Immunol. Methods 414 , 82-90, (2014)

Interferon gamma release assays (IGRAs) are widely used to detect pathogen specific cellular immunity. Cytomegalovirus (CMV) is the foremost problematic viral infection in immunocompromised patients s...

Bropirimine, an orally active anticancer agent for superficial bladder cancer.

Eur. Urol. 34(2) , 107-10, (1998)

To investigate efficacy and safety of bropirimine, a new orally active interferon inducer, in patients with superficial bladder cancer.Twenty patients with histologically confirmed recurrent superfici...

Current and new strategies in immunotherapy for superficial bladder cancer.

Urology 64(3) , 409-21, (2004)