Bumetanide

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Bumetanide
Systematic (IUPAC) name
3-butylamino-4-phenoxy-5-sulfamoyl-benzoic acid
Clinical data
Trade namesBumex
AHFS/Drugs.commonograph
MedlinePlusa684051
Pregnancy cat.B3 (AU) C (US)
Legal statusPrescription Only (S4) (AU) POM (UK) -only (US)
Routesoral
Pharmacokinetic data
Bioavailabilityalmost complete (~80%)
Protein binding97%
Metabolismhepatic
Half-life~0.8 hours
Excretionrenal
Identifiers
CAS number28395-03-1
ATC codeC03CA02
PubChemCID 2471
DrugBankDB00887
ChemSpider2377 YesY
UNII0Y2S3XUQ5H YesY
KEGGD00247 YesY
ChEBICHEBI:3213 YesY
ChEMBLCHEMBL1072 YesY
Chemical data
FormulaC17H20N2O5S 
Mol. mass364.417 g/mol
 YesY (what is this?)  (verify)
 
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Bumetanide
Systematic (IUPAC) name
3-butylamino-4-phenoxy-5-sulfamoyl-benzoic acid
Clinical data
Trade namesBumex
AHFS/Drugs.commonograph
MedlinePlusa684051
Pregnancy cat.B3 (AU) C (US)
Legal statusPrescription Only (S4) (AU) POM (UK) -only (US)
Routesoral
Pharmacokinetic data
Bioavailabilityalmost complete (~80%)
Protein binding97%
Metabolismhepatic
Half-life~0.8 hours
Excretionrenal
Identifiers
CAS number28395-03-1
ATC codeC03CA02
PubChemCID 2471
DrugBankDB00887
ChemSpider2377 YesY
UNII0Y2S3XUQ5H YesY
KEGGD00247 YesY
ChEBICHEBI:3213 YesY
ChEMBLCHEMBL1072 YesY
Chemical data
FormulaC17H20N2O5S 
Mol. mass364.417 g/mol
 YesY (what is this?)  (verify)

Bumetanide (trade names Bumex or Burinex) is 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. It is marketed by Hoffmann-La Roche. 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.[1]

Bumetanide is 40 times more potent than furosemide (for patients with normal renal function).[1]

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.[2]

Abuse

On October 24, 2008, ESPN reported a number of NFL players were being suspended under the steroid policy as a result of taking bumetanide. The drug is often used for weight loss, but also to mask other drugs or steroids by helping to dilute the contents of the user's urine, yielding a lower concentration of filtered substances which may then go undetected.

Bumetanide was an undisclosed active ingredient in the over the counter weight loss supplement StarCaps. StarCaps was pulled off the market after the presence of the undisclosed ingredient was discovered by the Food and Drug Administration.

References

  1. ^ a b Brunton, Laurence; Lazo, John S.; Parker, Keith L., eds. (2006). Goodman & Gilman's The Pharmacological Basis of Therapeutics (11th ed.). New York: McGraw-Hill. pp. 749–753. ISBN 0-07-142280-3. 
  2. ^ Kahle, K. T.; Barnett, S. M.; Sassower, K. C.; Staley, K. J. (2009). "Decreased Seizure Activity in a Human Neonate Treated With Bumetanide, an Inhibitor of the Na+–K+–2Cl Cotransporter NKCC1". Journal of Child Neurology 24 (5): 572–576. doi:10.1177/0883073809333526. PMID 19406757. 

External links