ブメタニド
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/08/21 08:21:49」(JST)
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Bumetanide
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| Systematic (IUPAC) name |
| 3-butylamino-4-phenoxy-5-sulfamoyl-benzoic acid |
| Clinical data |
| Trade names |
Bumex |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a684051 |
| Pregnancy cat. |
B3 (AU) C (US) |
| Legal status |
Prescription Only (S4) (AU) POM (UK) ℞-only (US) |
| Routes |
oral |
| Pharmacokinetic data |
| Bioavailability |
almost complete (~80%) |
| Protein binding |
97% |
| Metabolism |
hepatic |
| Half-life |
~0.8 hours |
| Excretion |
renal |
| Identifiers |
| CAS number |
28395-03-1 Y |
| ATC code |
C03CA02 |
| PubChem |
CID 2471 |
| DrugBank |
DB00887 |
| ChemSpider |
2377 Y |
| UNII |
0Y2S3XUQ5H Y |
| KEGG |
D00247 Y |
| ChEBI |
CHEBI:3213 Y |
| ChEMBL |
CHEMBL1072 Y |
| Chemical data |
| Formula |
C17H20N2O5S |
| Mol. mass |
364.417 g/mol |
SMILES
- O=S(=O)(c2cc(cc(NCCCC)c2Oc1ccccc1)C(=O)O)N
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InChI
-
InChI=1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23) Y
Key:MAEIEVLCKWDQJH-UHFFFAOYSA-N Y
|
Y (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[edit source | edit]
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[edit source | edit]
- ^ 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.
- ^ 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[edit source | edit]
- Bumex [1] (FDA)
- Bumetanide (patient information)
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Symporter inhibitors
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|
| Sodium chloride |
- thiazide: Bendroflumethiazide
- Chlorothiazide
- Cyclopenthiazide
- Cyclothiazide
- Hydrochlorothiazide
- Hydroflumethiazide
- Methyclothiazide
- Polythiazide
- Trichlormethiazide
other: Chlorthalidone
- Metolazone
|
|
| Sodium, potassium, chloride |
|
|
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Antihypertensives: diuretics (C03)
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Sulfonamides
(and etacrynic acid) |
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CA inhibitors (at PT)
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|
|
|
Loop (Na-K-Cl at AL)
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- Furosemide#
- Bumetanide
- Etacrynic acid
- Etozoline
- Muzolimine
- Piretanide
- Tienilic acid
- Torasemide
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|
|
Thiazides (Na-Cl at DCT,
Calcium-sparing)
|
- Hydrochlorothiazide#
- Bendroflumethiazide
- Hydroflumethiazide
- Chlorothiazide
- Polythiazide
- Trichlormethiazide
- Cyclopenthiazide
- Methyclothiazide
- Cyclothiazide
- Mebutizide
|
|
|
Thiazide-likes (primarily DCT)
|
- Quinethazone
- Clopamide
- Chlortalidone
- Mefruside
- Clofenamide
- Metolazone
- Meticrane
- Xipamide
- Indapamide
- Clorexolone
- Fenquizone
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|
|
| Potassium-sparing (at CD) |
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ESC blockers
|
- Amiloride#
- Triamterene
- Benzamil
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|
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Aldosterone antagonists
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- Spironolactone#
- Eplerenone
- Potassium canrenoate
- Canrenone
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|
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| Osmotic diuretics (PT, DL) |
|
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Vasopressin receptor antagonists
(DCT and CD) |
- vaptans: Conivaptan
- Mozavaptan
- Satavaptan
- Tolvaptan
- tetracyclines: Demeclocycline
|
|
| Other |
- mercurial diuretic (Mersalyl, Meralluride)
- Theobromine
- Cicletanine
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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|
anat (a:h/u/t/a/l,v:h/u/t/a/l)/phys/devp/cell/prot
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noco/syva/cong/lyvd/tumr, sysi/epon, injr
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proc, drug (C2s+n/3/4/5/7/8/9)
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UpToDate Contents
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English Journal
- Increased Slc12a1 expression in β-cells and improved glucose disposal in Slc12a2 heterozygous mice.
- Alshahrani S1, Almutairi MM1, Kursan S1, Dias-Junior E1, Almiahuob MM1, Aguilar-Bryan L1, Di Fulvio M2.
- The Journal of endocrinology.J Endocrinol.2015 Dec;227(3):153-65. doi: 10.1530/JOE-15-0327. Epub 2015 Sep 23.
- The products of the Slc12a1 and Slc12a2 genes, commonly known as Na(+)-dependent K(+)2Cl(-) co-transporters NKCC2 and NKCC1, respectively, are the targets for the diuretic bumetanide. NKCCs are implicated in the regulation of intracellular chloride concentration ([Cl(-)]i) in pancreatic β-cells, an
- PMID 26400961
- Secretion of Na(+), K(+) and fluid by the Malpighian (renal) tubule of the larval cabbage looper Trichoplusia ni (Lepidoptera: Noctuidae).
- Ruiz-Sanchez E1, O'Donnell MJ2, Donini A3.
- Journal of insect physiology.J Insect Physiol.2015 Nov;82:92-8. doi: 10.1016/j.jinsphys.2015.09.007.
- The Malpighian (renal) tubules play important roles in ionic and osmotic homeostasis in insects. In Lepidoptera, the Malpighian tubules are structurally regionalized and the concentration of Na(+) and K(+) in the secreted fluid varies depending on the segment of tubule analyzed. In this work, we hav
- PMID 26432549
- Acute temperature sensitivity in optic nerve axons explained by an electrogenic membrane potential.
- Coates TA1, Woolnough O1, Masters JM1, Asadova G1, Chandrakumar C1, Baker MD2.
- Pflügers Archiv : European journal of physiology.Pflugers Arch.2015 Nov;467(11):2337-49. doi: 10.1007/s00424-015-1696-2. Epub 2015 Feb 28.
- Classical work in squid axon reports resting membrane potential is independent of temperature, but our findings suggest that this is not the case for axons in mammalian optic nerve. Refractory period duration changes over 10 times between 37 °C and room temperature, and afterpotential polarity is
- PMID 25724933
Related Links
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