sodium 3-(aminosulphonyl)-5-(butylamino)-4-phenoxybenzoate

Names

[ Name ]:
sodium 3-(aminosulphonyl)-5-(butylamino)-4-phenoxybenzoate

[Synonym ]:
Sodium 3-(aminosulphonyl)-5-(butylamino)-4-phenoxybenzoate
Sodium 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoate
Benzoic acid,3-(aminosulfonyl)-5-(butylamino)-4-phenoxy-,sodium salt (1:1)
SODIUM 3-(AMINOSULFONYL)-5-(BUTYLAMINO)-4-PHENOXYBENZOATE
Benzoic acid,3-(butylamino)-4-phenoxy-5-sulfamoyl-,monosodium salt (8CI)
EINECS 249-015-6
sodium bumetanide
Benzoicacid,3-(aminosulfonyl)-5-(butylamino)-4-phenoxy-,monosodium salt (9CI)

Biological Activity

[Description]:

Bumetanide sodium, a highly potent loop diuretic, is a Na+-K+-Cl+ cotransporter (NKCC) blocker. Bumetanide sodium is a selective NKCC1 inhibitor, and also inhibits NKCC2, with IC50s of 0.68 and 4.0 μM for hNKCC1A and hNKCC2A, respectively[1][2].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> NKCC

Research Areas >> Metabolic Disease

[In Vitro]

Bumetanide sodium has inhibitory effects for the two major human splice variants of NKCCs, hNKCC1A and hNKCC2A [1]. Bumetanide sodium (0.03-100 μM; 5 minutes) inhibits the 86Rb+ uptake in NKCC1A-expressing oocytes in a dose-dependent manner[1]. Bumetanide sodium inhibits NKCC2 isoform B in HEK-293 cells with an IC50 value of 0.54 μM[2].

[In Vivo]

Bumetanide sodium (7.6-30.4 mg/kg; i.v.) attenuates the decrease in apparent diffusion coefficients (ADC) ratios for both cortex and striatum (by 40-67%), indicating reduced edema formation[3]. Bumetanide sodium also reduces infarct size[3]. Bumetanide sodium shows different half-lives of 21.4 min, 53.8 min and 137 min following 2 mg/kg, 8 mg/kg and 20 mg/kg intravenous injection, respectively, in rats[4].

[References]

[1]. Lykke K, et al. The search for NKCC1-selective drugs for the treatment of epilepsy: Structure-function relationship of bumetanide and various bumetanide derivatives in inhibiting the human cation-chloride cotransporter NKCC1A. Epilepsy Behav. 2016 Jun;59:42-9.

[2]. Ciaran Richardson, et al. Regulation of the NKCC2 ion cotransporter by SPAK-OSR1-dependent and -independent pathways. J Cell Sci. 2011 Mar 1;124(Pt 5):789-800.

[3]. Martha E O'Donnell, et al. Bumetanide inhibition of the blood-brain barrier Na-K-Cl cotransporter reduces edema formation in the rat middle cerebral artery occlusion model of stroke. J Cereb Blood Flow Metab. 2004 Sep;24(9):1046-56.

[4]. S H Lee, et al. Pharmacokinetics and pharmacodynamics of bumetanide after intravenous and oral administration to rats: absorption from various GI segments. J Pharmacokinet Biopharm. 1994 Feb;22(1):1-17.6

Chemical & Physical Properties

[ Boiling Point ]:
571.2ºC at 760mmHg

[ Molecular Formula ]:
C₁₇H₁₉N₂NaO₅S

[ Molecular Weight ]:
386.39800

[ Flash Point ]:
299.3ºC

[ Exact Mass ]:
386.09100

[ PSA ]:
129.93000

[ LogP ]:
3.55590

[ Vapour Pressure ]:
6.89E-14mmHg at 25°C

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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