Bumetanide

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Synonyms: Bumetanide, 3-(Aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acid, Bumex, Burinex

IUPAC Name:

Functional Activity:

Bumetanide is a Na⁺/2Cl^-/K⁺ (NKCC) co-transporter inhibitor. In the brain, bumetanide blocks the NKCC1 cation-chloride co-transporter, and thus decreases internal chloride concentration in neurons. In turn, this concentration change makes the action of GABA more hyperpolarizing, which may be useful for treatment of neonatal seizures, that quite often are not responsive to traditional GABA-targeted treatment, such as barbiturates. Bumetanide is therefore currently under evaluation as a prospective antiepileptic drug.

Bumetanide is also a loop diuretic of the sulfamyl category to treat heart failure. It is often used in people in whom high doses of furosemide are ineffective. The main difference between the two substances is in bioavailability and pharmacodynamic potency. Furosemide is incompletely absorbed in the intestine (60%), and there is substantial inter- and intraindividual differences in bioavailability (range 10-90%). Bumetanide is almost completely absorbed (80%), and the absorption is not altered when it is taken with food. It is said to be a more predictable diuretic, meaning that the predictable absorption is reflected in a more predictable effect. Bumetanide is 40 times more potent than furosemide.

Technical Data:

M.Wt: 364.42

Formula: C₁₇H₂₀N₂O₅S

Solubility: Soluble in DMSO

Purity: >98%

Storage: Dessicate at RT

CAS No.: 28395-03-1

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References for bumetanide:

1. Pollo, F., Sequinel, R., Rufino, J. L., Los Weinert, P., Pezza, H. R., and Pezza, L. An environmentally friendly reflectometric method for bumetanide determination in pharmaceuticals. Anal Sci, 25: 897-901, 2009.

2. Vanhatalo, S., Hellstrom-Westas, L., and De Vries, L. S. Bumetanide for neonatal seizures: Based on evidence or enthusiasm? Epilepsia, 50: 1292-1293, 2009.

3. Kahle, K. T., Barnett, S. M., Sassower, K. C., and Staley, K. J. Decreased seizure activity in a human neonate treated with bumetanide, an inhibitor of the Na(+)-K(+)-2Cl(-) cotransporter NKCC1. J Child Neurol, 24: 572-576, 2009.

4. Migliati, E., Meurice, N., DuBois, P., Fang, J. S., Somasekharan, S., Beckett, E., Flynn, G., and Yool, A. J. Inhibition of aquaporin-1 and aquaporin-4 water permeability by a derivative of the loop diuretic bumetanide acting at an internal pore-occluding binding site. Mol Pharmacol, 76: 105-112, 2009.

5. Nardou, R., Ben-Ari, Y., and Khalilov, I. Bumetanide, an NKCC1 antagonist, does not prevent formation of epileptogenic focus but blocks epileptic focus seizures in immature rat hippocampus. J Neurophysiol, 101: 2878-2888, 2009.

6. Mazarati, A., Shin, D., and Sankar, R. Bumetanide inhibits rapid kindling in neonatal rats. Epilepsia, 50: 2117-2122, 2009.

Certificate of Analysis/MSDS is available upon request with lot number