A loop diuretic and an inhibitor of NKCC1 and NKCC2
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Analytical Standard(s)
26298Furosemide
Labeled Version(s)
31789Furosemide-d5
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Furosemide

Item No. 17273

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]-benzoic acid
CAS Number
54-31-9
Synonyms
  • Frusemide
Molecular Formula
C12H11ClN2O5S
Formula Weight
330.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 10 mg/ml
λmax
234, 273, 343 nm
SMILES
ClC1=C(S(N)(=O)=O)C=C(C(O)=O)C(NCC2=CC=CO2)=C1
InChi Code
InChI=1S/C12H11ClN2O5S/c13-9-5-10(15-6-7-2-1-3-20-7)8(12(16)17)4-11(9)21(14,18)19/h1-5,15H,6H2,(H,16,17)(H2,14,18,19)
InChi Key
ZZUFCTLCJUWOSV-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

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    5 g

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    Product Description

    Furosemide is a loop diuretic and an inhibitor of the Na+/K+/2Cl- (NKCC) cotransporters, NKCC1 and NKCC2 (Kis = ~10 µM for both).1,2 In vivo, furosemide (0.1 mg/kg, p.o.) increases diuresis in beagle dogs.3 Furosemide (30 mg/kg) reduces ventricular collagen deposition and fibrosis in a rat model of dilated cardiomyopathy.4 It is also an inhibitor of carbonic anhydrase I (CAI), CAII, and CAIII (Kis = 0.052-0.065 µM) and organic ion transporter 1 (OAT1; Ki = 9.5 µM), as well as a GABAA receptor antagonist.5,6,7 This product is also available as an analytical reference standard (Item No. 26298).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gillen, C.M., Brill, S., Payne, J.A., et al. Molecular cloning and functional expression of the K-Cl cotransporter from rabbit, rat, and human. A new member of the cation-chloride cotransporter family. The Journal of Biological Chemisty 271(27), 16237-16244 (1996).

    2. Markadieu, N., and Delpire, E. Physiology and pathophysiology of SLC12A1/2 transporters. Pflugers Arch. 466(1), 91-105 (2014).

    3. Potter, B.M., Ames, M.K., Hess, A., et al. Comparison between the effects of torsemide and furosemide on the reninangiotensin-aldosterone system of normal dogs. J. Vet. Cardiol. 26, 51-62 (2019).

    4. Watanabe, K., Sreedhar, R., Thandavarayan, R.A., et al. Comparative effects of torasemide and furosemide on gap junction proteins and cardiac fibrosis in a rat model of dilated cardiomyopathy. Biofactors 43(2), 187-194 (2017).

    5. Temperini, C., Cecchi, A., Scozzafava, A., et al. Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide-isozyme II adduct. Bioorg. Med. Chem. Lett. 18(8), 2567-2573 (2008).

    6. Rajan, S.T., Kumar, M.K., and Ramakrishna, M. The novel process for the preparation of (1R,2R,3aS,9aS)-[[2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]inden-5-yl]-oxy]acetic acid. (2014).

    7. Siess, W., Siegel, F.L., and Lapetina, E.G. Dihomogammalinolenic acid, but not eicosapentaenoic acid, activates washed human platelets. Biochim. Biophys. Acta 801(2), 265-276 (1984).