Bumetanide| PF15593| CAS#: 28395-03-1 | MedKoo Biosciences Inc.

Bumetanide
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317355

CAS#: 28395-03-1

Description: 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.

Chemical Structure

Bumetanide

CAS# 28395-03-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317355
Name: Bumetanide
CAS#: 28395-03-1
Chemical Formula: C17H20N2O5S
Exact Mass: 364.11
Molecular Weight: 364.416
Elemental Analysis: C, 56.03; H, 5.53; N, 7.69; O, 21.95; S, 8.80

Price and Availability

Size	Price	Availability
500mg	USD 200	2 Weeks
1g	USD 350
2g	USD 550
5g	USD 950	2 Weeks
10g	USD 1450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Bumetanide, Trade names: Bumex or Burinex; PF 1593, PF-1593, PF1593; Ro 10-6338; Ro10-6338

IUPAC/Chemical Name: 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid

InChi Key: MAEIEVLCKWDQJH-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(O)C1=CC(S(=O)(N)=O)=C(OC2=CC=CC=C2)C(NCCCC)=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Bumetanide (Ro 10-6338; PF 1593), a highly potent loop diuretic, is a Na+-K+-Cl+ cotransporter (NKCC) blocker.
In vitro activity:	The addition of bumetanide (20μM) to the culture medium prevented the ethanol-induced escalation of Nkx2.1+ interneuron migration into the cortex with no significant difference observed compared to control (Figure 3a and b; EtOH+Bumet x− = 61.1 ± 2.4 cells, 10 cultures; P > 0.999; effect size ω2 for treatment = 0.23). Reference: eLife. 2019; 8: e48648. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6768659/
In vivo activity:	This study further found that the decrease in head-dipping behavior caused by diazepam was blocked by bumetanide, a Na+-K+-2Cl- cotransporter isoform 1 (NKCC1) antagonist, in LPS-treated mice. Reference: Eur J Pharmacol. 2021 Aug 5;904:174195. https://pubmed.ncbi.nlm.nih.gov/34004209/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	53.8	147.66
	DMF	33.0	90.56
	DMF:PBS (pH 7.2) (1:1)	0.5	1.37
	Ethanol	20.7	56.72

Preparing Stock Solutions

The following data is based on the product molecular weight 364.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Skorput AG, Lee SM, Yeh PW, Yeh HH. The NKCC1 antagonist bumetanide mitigates interneuronopathy associated with ethanol exposure in utero. Elife. 2019 Sep 23;8:e48648. doi: 10.7554/eLife.48648. PMID: 31545168; PMCID: PMC6768659. 2. Dzhala V, Staley KJ. Acute and chronic efficacy of bumetanide in an in vitro model of posttraumatic epileptogenesis. CNS Neurosci Ther. 2015 Feb;21(2):173-80. doi: 10.1111/cns.12369. Epub 2014 Dec 12. PMID: 25495911; PMCID: PMC4391014. 3. Matsumoto D, Ushio S, Wada Y, Noda Y, Esumi S, Izushi Y, Kitamura Y, Sendo T. Bumetanide prevents diazepam-modified anxiety-like behavior in lipopolysaccharide-treated mice. Eur J Pharmacol. 2021 Aug 5;904:174195. doi: 10.1016/j.ejphar.2021.174195. Epub 2021 May 15. PMID: 34004209. 4. Palaniappan B, Solomon AP, C DR. Targeting AgrA quorum sensing regulator by bumetanide attenuates virulence in Staphylococcus aureus - A drug repurposing approach. Life Sci. 2021 May 15;273:119306. doi: 10.1016/j.lfs.2021.119306. Epub 2021 Mar 1. PMID: 33662434.
In vitro protocol:	1. Skorput AG, Lee SM, Yeh PW, Yeh HH. The NKCC1 antagonist bumetanide mitigates interneuronopathy associated with ethanol exposure in utero. Elife. 2019 Sep 23;8:e48648. doi: 10.7554/eLife.48648. PMID: 31545168; PMCID: PMC6768659. 2. Dzhala V, Staley KJ. Acute and chronic efficacy of bumetanide in an in vitro model of posttraumatic epileptogenesis. CNS Neurosci Ther. 2015 Feb;21(2):173-80. doi: 10.1111/cns.12369. Epub 2014 Dec 12. PMID: 25495911; PMCID: PMC4391014.
In vivo protocol:	1. Matsumoto D, Ushio S, Wada Y, Noda Y, Esumi S, Izushi Y, Kitamura Y, Sendo T. Bumetanide prevents diazepam-modified anxiety-like behavior in lipopolysaccharide-treated mice. Eur J Pharmacol. 2021 Aug 5;904:174195. doi: 10.1016/j.ejphar.2021.174195. Epub 2021 May 15. PMID: 34004209. 2. Palaniappan B, Solomon AP, C DR. Targeting AgrA quorum sensing regulator by bumetanide attenuates virulence in Staphylococcus aureus - A drug repurposing approach. Life Sci. 2021 May 15;273:119306. doi: 10.1016/j.lfs.2021.119306. Epub 2021 Mar 1. PMID: 33662434.

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1: Brater DC, Day B, Burdette A, Anderson S. Bumetanide and furosemide in heart failure. Kidney Int. 1984 Aug;26(2):183-9. doi: 10.1038/ki.1984.153. PMID: 6503136.

2: Sprengers JJ, van Andel DM, Zuithoff NPA, Keijzer-Veen MG, Schulp AJA, Scheepers FE, Lilien MR, Oranje B, Bruining H. Bumetanide for Core Symptoms of Autism Spectrum Disorder (BAMBI): A Single Center, Double-Blinded, Participant- Randomized, Placebo-Controlled, Phase-2 Superiority Trial. J Am Acad Child Adolesc Psychiatry. 2021 Jul;60(7):865-876. doi: 10.1016/j.jaac.2020.07.888. Epub 2020 Jul 27. PMID: 32730977.

3: Tao D, Liu F, Sun X, Qu H, Zhao S, Zhou Z, Xiao T, Zhao C, Zhao M. Bumetanide: A review of its neuroplasticity and behavioral effects after stroke. Restor Neurol Neurosci. 2019;37(4):397-407. doi: 10.3233/RNN-190926. PMID: 31306143.

4: James BJ, Gales MA, Gales BJ. Bumetanide for Autism Spectrum Disorder in Children: A Review of Randomized Controlled Trials. Ann Pharmacother. 2019 May;53(5):537-544. doi: 10.1177/1060028018817304. Epub 2018 Dec 2. PMID: 30501497.

5: Staley KJ. Clarifications regarding bumetanide for neonatal seizures. Epilepsia. 2022 Jul;63(7):1863-1867. doi: 10.1111/epi.17278. Epub 2022 May 26. PMID: 35524444; PMCID: PMC9283319.

6: Ward A, Heel RC. Bumetanide. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic use. Drugs. 1984 Nov;28(5):426-64. doi: 10.2165/00003495-198428050-00003. PMID: 6391889.

7: Halstenson CE, Matzke GR. Bumetanide: a new loop diuretic (Bumex, Roche Laboratories). Drug Intell Clin Pharm. 1983 Nov;17(11):786-97. doi: 10.1177/106002808301701101. PMID: 6357686.

8: Olsen UB. The pharmacology of bumetanide. Acta Pharmacol Toxicol (Copenh). 1977;41(3):1-29. doi: 10.1111/j.1600-0773.1977.tb03209.x. PMID: 331869.

9: Kaila K, Löscher W. Bumetanide for neonatal seizures: No light in the pharmacokinetic/dynamic tunnel. Epilepsia. 2022 Jul;63(7):1868-1873. doi: 10.1111/epi.17279. Epub 2022 May 26. PMID: 35524446; PMCID: PMC9545618.

10: Hinchcliff KW, Mitten LA. Furosemide, bumetanide, and ethacrynic acid. Vet Clin North Am Equine Pract. 1993 Dec;9(3):511-22. doi: 10.1016/s0749-0739(17)30383-8. PMID: 8299013.

11: Fernell E, Gustafsson P, Gillberg C. Bumetanide for autism: Open-label trial in six children. Acta Paediatr. 2021 May;110(5):1548-1553. doi: 10.1111/apa.15723. Epub 2021 Jan 21. PMID: 33336381; PMCID: PMC8248373.

12: Editorial: Bumetanide. Lancet. 1975 Nov 1;2(7940):860. PMID: 53339.

13: Brater DC, Chennavasin P, Day B, Burdette A, Anderson S. Bumetanide and furosemide. Clin Pharmacol Ther. 1983 Aug;34(2):207-13. doi: 10.1038/clpt.1983.154. PMID: 6872415.

14: Ben-Ari Y, Cherubini E. The GABA Polarity Shift and Bumetanide Treatment: Making Sense Requires Unbiased and Undogmatic Analysis. Cells. 2022 Jan 24;11(3):396. doi: 10.3390/cells11030396. PMID: 35159205; PMCID: PMC8834580.

15: Leitao EA, Person JR. Bumetanide-induced pseudoporphyria. J Am Acad Dermatol. 1990 Jul;23(1):129-30. doi: 10.1016/s0190-9622(08)81209-1. PMID: 2365864.

16: Lv H, Gu X, Shan X, Zhu T, Ma B, Zhang HT, Bambini-Junior V, Zhang T, Li WG, Gao X, Li F. Nanoformulated Bumetanide Ameliorates Social Deficiency in BTBR Mice Model of Autism Spectrum Disorder. Front Immunol. 2022 May 23;13:870577. doi: 10.3389/fimmu.2022.870577. PMID: 35693812; PMCID: PMC9179025.

17: Ben-Ari Y, Lemonnier E. Using bumetanide to treat autism appears promising but further clinical trials are needed to confirm this approach. Acta Paediatr. 2021 May;110(5):1395-1397. doi: 10.1111/apa.15747. Epub 2021 Jan 23. PMID: 33484191.

18: Löscher W, Kaila K. CNS pharmacology of NKCC1 inhibitors. Neuropharmacology. 2022 Mar 1;205:108910. doi: 10.1016/j.neuropharm.2021.108910. Epub 2021 Dec 6. PMID: 34883135.

19: Metayer T, Orset C, Ali C, Furon J, Szabla N, Emery E, Vivien D, Gaberel T. Bumetanide lowers acute hydrocephalus in a rat model of subarachnoid hemorrhage. Acta Neurochir (Wien). 2022 Feb;164(2):499-505. doi: 10.1007/s00701-021-05088-4. Epub 2022 Jan 30. PMID: 35094147.

20: Pines A. Letter: Bumetanide. Lancet. 1975 Nov 29;2(7944):1093. doi: 10.1016/s0140-6736(75)90468-7. PMID: 53579.

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