| Identification | Back Directory | [Name]
(R)-BPO-27 | [CAS]
1415390-47-4 | [Synonyms]
BPO-27
(R)-BPO-27
6H-Pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]benzoxazine-2-carboxylic acid, 6-(5-bromo-2-furanyl)-7,8,9,10-tetrahydro-7,9-dimethyl-8,10-dioxo-11-phenyl-, (6R)-
BENZOPYRIMIDO-PYRROLO-OXAZINEDIONE BPO-27 [6-(5-BROMOFURAN-2-YL)-7,9-DIMETHYL-8,10-DIOXO- 11-PHENYL-7,8,9,10-TETRAHYDRO-6H-BENZO[B]PYRIMIDO [49,59: 3,4]PYRROLO [1,2-D][1,4]OXAZINE-2-CARBOXYLIC ACID] | [Molecular Formula]
C26H18BrN3O6 | [MDL Number]
MFCD30532675 | [MOL File]
1415390-47-4.mol | [Molecular Weight]
548.34 |
| Chemical Properties | Back Directory | [Boiling point ]
732.9±70.0 °C(Predicted) | [density ]
1.68±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO:14.28(Max Conc. mg/mL);26.04(Max Conc. mM) | [form ]
Solid | [pka]
3.76±0.40(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Description]
BPO-27 is a potent and metabolically stable CFTR inhibitor. | [Uses]
(R)-BPO-27, the R enantiomer of BPO-27, is a potent, orally active and ATP-competitive CFTR?inhibitor with an?IC50 of 4 nM. | [in vivo]
(R)-BPO-27 (interperitoneal administration; 10 mg/kg)?decays with t1/2≈1.6 h and gives sustained therapeutic concentrations in kidney in a PK study[1].(R)-BPO-27 (intraperitoneal injection; 5 mg/kg; 30 min before abdominal surgery) prevents fluid accumulation in closed midjejunal loops produced by cholera toxin, giving an intestinal loop weight/length ratio similar to that in PBS-injected loops. This effect is dose-dependently and the IC50 value is 0.1 mg/kg[3].(R)-BPO-27 (intraperitoneal injection or oral administration; 5 mg/kg) shows a slow (R)-BPO-27 metabolism and produces sustained serum (R)-BPO-27 levels for at least 4 h. The AUC analysis gave an oral bioavailability of ～94% for (R)-BPO-27 in mouse pharmacokinetics and toxicity study[3]. | Animal Model: | Female CD1 mice (age 8–10 wk)[3] | | Dosage: | 0.05, 0.15, 0.5, 1.5, and 5 mg/kg | | Administration: | Intraperitoneal injection; 5 mg/kg; 30 min before abdominal surgery | | Result: | Exhibited apparent efficacy in mice models of cholera and traveler’s diarrhea. |
| [target]
(R)-BPO-27, the R enantiomer of BPO-27, is a potent, orally active and ATP-competitive CFTR inhibitor with an IC50 of 4 nM. | [storage]
Store at -20°C | [References]
[1] Snyder DS, et al. Absolute Configuration And Biological Properties of Enantiomers of CFTR Inhibitor BPO-27. ACS Med Chem Lett. 2013 May 9;4(5):456-459. DOI:10.1021/ml400069k
[2] Kim Y, et al. Benzopyrimido-pyrrolo-oxazine-dione (R)-BPO-27 Inhibits CFTR Chloride Channel Gating by Competition with ATP. Mol Pharmacol. 2015 Oct;88(4):689-96. DOI:10.1124/mol.115.098368
[3] Onur Cil, et al.Benzopyrimido-pyrrolo-oxazine-dione CFTR inhibitor (R)-BPO-27 for antisecretory therapy of diarrheas caused by bacterial enterotoxins. FASEB J. 2017 Feb;31(2):751-760. DOI:10.1096/fj.201600891R |
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BOC Sciences
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https://www.bocsci.com |
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