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56741-95-8

56741-95-8 structure
56741-95-8 structure
  • Name: Bropirimine
  • Chemical Name: 2-Amino-5-bromo-4-hydroxy-6-phenylpyrimidine
  • CAS Number: 56741-95-8
  • Molecular Formula: C10H8BrN3O
  • Molecular Weight: 266.094
  • Catalog: Signaling Pathways Immunology/Inflammation Toll-like Receptor (TLR)
  • Create Date: 2018-11-30 18:00:20
  • Modify Date: 2024-01-10 03:27:02
  • 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].
Name 2-Amino-5-bromo-4-hydroxy-6-phenylpyrimidine
Synonyms 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
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
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.
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

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
Symbol GHS08
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
56741-94-7 structure

56741-94-7

~50%

56741-95-8 structure

56741-95-8
Literature: Evenaes, Johan; Edfeldt, Fredrik; Lepistoe, Matti; Svitacheva, Naila; Synnergren, Anna; Lundquist, Britta; Graense, Mia; Roennholm, Anna; Varga, Mikael; Wright, John; Wei, Min; Yue, Sherrie; Wang, Junfeng; Li, Chong; Li, Xuan; Chen, Gang; Liao, Yong; Lv, Gang; Tjoernebo, Ann; Narjes, Frank Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 5 p. 1315 - 1321
94-02-0 structure

94-02-0

~%

56741-95-8 structure

56741-95-8
Literature: Journal of Medicinal Chemistry, , vol. 28, # 12 p. 1864 - 1869
98-88-4 structure

98-88-4

~%

56741-95-8 structure

56741-95-8
Literature: Journal of Medicinal Chemistry, , vol. 23, # 3 p. 237 - 239
614-27-7 structure

614-27-7

~%

56741-95-8 structure

56741-95-8
Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 24, # 5 p. 1315 - 1321
93-58-3 structure

93-58-3

~%

56741-95-8 structure

56741-95-8
Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 24, # 5 p. 1315 - 1321
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%

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title: CAS No. 56741-95-8 | Chemsrc address: https://m.chemsrc.com/en/baike/329770.html

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