Bumetanide

• CAT Number: A000244
• CAS Number: 28395-03-1
• Molecular Formula: C17H20N2O5S
• Molecular Weight: 364.4
• Purity: ≥95%
• Synonyms: 28395-03-1; 3-(Butylamino)-4-phenoxy-5-sulfamoylbenzoic acid; Bumex; Burinex; Fordiuran
• Target: NKCC
• Solubility: >18.2mg/mL in DMSO
• Storage: -20°C
• 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)
• InChIKey: MAEIEVLCKWDQJH-UHFFFAOYSA-N
• SMILES: CCCCNC1=C(C(=CC(=C1)C(=O)O)S(=O)(=O)N)OC2=CC=CC=C2

Bumetanide 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 are 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.

Reference

1: Vlaskamp C, Poil SS, Jansen F, Linkenkaer-Hansen K, Durston S, Oranje B,
Bruining H. Bumetanide As a Candidate Treatment for Behavioral Problems in
Tuberous Sclerosis Complex. Front Neurol. 2017 Sep 8;8:469. doi:
10.3389/fneur.2017.00469. eCollection 2017. PubMed PMID: 28943860; PubMed Central
PMCID: PMC5596068.

2: Hu D, Yu ZL, Zhang Y, Han Y, Zhang W, Lu L, Shi J. Bumetanide treatment during
early development rescues maternal separation-induced susceptibility to stress.
Sci Rep. 2017 Sep 19;7(1):11878. doi: 10.1038/s41598-017-12183-z. PubMed PMID:
28928398; PubMed Central PMCID: PMC5605528.

3: Fluegge K. Bumetanide Treatment for Psychiatric Disorders and the Modulation
of Central Nitric Oxide Metabolism. Clin Neuropharmacol. 2017
Jul/Aug;40(4):192-193. doi: 10.1097/WNF.0000000000000228. PubMed PMID: 28704252.

4: Lemonnier E, Villeneuve N, Sonie S, Serret S, Rosier A, Roue M, Brosset P,
Viellard M, Bernoux D, Rondeau S, Thummler S, Ravel D, Ben-Ari Y. Effects of
bumetanide on neurobehavioral function in children and adolescents with autism
spectrum disorders. Transl Psychiatry. 2017 May 9;7(5):e1124. doi:
10.1038/tp.2017.101. PubMed PMID: 28485727; PubMed Central PMCID: PMC5534937.

5: Lemonnier E, Villeneuve N, Sonie S, Serret S, Rosier A, Roue M, Brosset P,
Viellard M, Bernoux D, Rondeau S, Thummler S, Ravel D, Ben-Ari Y. Effects of
bumetanide on neurobehavioral function in children and adolescents with autism
spectrum disorders. Transl Psychiatry. 2017 Mar 14;7(3):e1056. doi:
10.1038/tp.2017.10. PubMed PMID: 28291262; PubMed Central PMCID: PMC5416661.

6: Römermann K, Fedrowitz M, Hampel P, Kaczmarek E, Töllner K, Erker T, Sweet DH,
Löscher W. Multiple blood-brain barrier transport mechanisms limit bumetanide
accumulation, and therapeutic potential, in the mammalian brain.
Neuropharmacology. 2017 May 1;117:182-194. doi: 10.1016/j.neuropharm.2017.02.006.
Epub 2017 Feb 10. PubMed PMID: 28192112.

7: Hu JJ, Yang XL, Luo WD, Han S, Yin J, Liu WH, He XH, Peng BW. Bumetanide
reduce the seizure susceptibility induced by pentylenetetrazol via inhibition of
aberrant hippocampal neurogenesis in neonatal rats after hypoxia-ischemia. Brain
Res Bull. 2017 Apr;130:188-199. doi: 10.1016/j.brainresbull.2017.01.022. Epub
2017 Feb 2. PubMed PMID: 28161194.

8: Tang L, Fang X, Winesett SP, Cheng CY, Binder HJ, Rivkees SA, Cheng SX.
Bumetanide increases Cl–dependent short-circuit current in late distal colon:
Evidence for the presence of active electrogenic Cl- absorption. PLoS One. 2017
Feb 2;12(2):e0171045. doi: 10.1371/journal.pone.0171045. eCollection 2017. PubMed
PMID: 28152000; PubMed Central PMCID: PMC5289505.

9: Rahmanzadeh R, Eftekhari S, Shahbazi A, Khodaei Ardakani MR, Rahmanzade R,
Mehrabi S, Barati M, Joghataei MT. Effect of bumetanide, a selective NKCC1
inhibitor, on hallucinations of schizophrenic patients; a double-blind randomized
clinical trial. Schizophr Res. 2017 Jun;184:145-146. doi:
10.1016/j.schres.2016.12.002. Epub 2016 Dec 9. PubMed PMID: 27956008.

10: Rahmanzadeh R, Shahbazi A, Ardakani MK, Mehrabi S, Rahmanzade R, Joghataei
MT. Lack of the effect of bumetanide, a selective NKCC1 inhibitor, in patients
with schizophrenia: A double-blind randomized trial. Psychiatry Clin Neurosci.
2017 Jan;71(1):72-73. doi: 10.1111/pcn.12475. Epub 2016 Dec 21. PubMed PMID:
27800670.