Banner
Identification
Name Furosemide
Accession Number DB00695 (APRD00608, DB07799)
Type small molecule
Groups approved
Description

A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for edema and chronic renal insufficiency. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Dihydroflumethiazide
  • Frusemid
  • Frusemide
  • Furosemid
  • Furosemida [INN-Spanish]
  • Furosemidu [Polish]
  • Furosemidum [INN-Latin]
  • Fursemid
  • Fursemida
  • Fursemide
  • Metflorylthiazidine
  • Methforylthiazidine
Brand names
  • Aisemide
  • Aldalix
  • Aldic
  • Aluzine
  • Anfuramaide
  • Apo-Frusemide
  • Apo-Furosemide
  • Aquarid
  • Aquasin
  • Arasemide
  • Beronald
  • Bioretic
  • Bristab
  • Bristurin
  • Cetasix
  • Depix
  • Desal
  • Desdemin
  • Di-Ademil
  • Dirine
  • Disal
  • Discoid
  • Disemide
  • Diucardin
  • Diumide-K
  • Diural
  • Diurapid
  • Diuretic Salt
  • Diurin
  • Diurolasa
  • Diusemide
  • Diusil
  • Diuzol
  • Dranex
  • Dryptal
  • Durafurid
  • Edemid
  • Edenol
  • Eliur
  • Elodrine
  • Endural
  • Errolon
  • Eutensin
  • Farsix
  • Finuret
  • Fluidrol
  • Fluss
  • Franyl
  • Frumex
  • Frumide
  • Frumil
  • Frusedan
  • Frusema
  • Frusemin
  • Frusenex
  • Frusetic
  • Frusid
  • Fulsix
  • Fuluvamide
  • Fuluvamine
  • Furanthril
  • Furanthryl
  • Furantril
  • Furanturil
  • Furesis
  • Furetic
  • Furex
  • Furfan
  • Furix
  • Furmid
  • Furo-Basan
  • Furo-Puren
  • Furobeta
  • Furocot
  • Furodiurol
  • Furodrix
  • Furomen
  • Furomex
  • Furomide M.D.
  • Furorese
  • Furosan
  • Furose
  • Furosedon
  • Furosemix
  • Furoside
  • Furosifar
  • Furosix
  • Furoter
  • Furovite
  • Fursol
  • Fusid
  • Golan
  • Hissuflux
  • Hydol
  • Hydrenox
  • Hydrex
  • Hydro
  • Hydro-Rapid
  • Hydroled
  • Impugan
  • Jenafusid
  • Katlex
  • Kofuzon
  • Kolkin
  • Kutrix
  • Lasemid
  • Lasex
  • Lasiletten
  • Lasilix
  • Lasix
  • Lasix Retard
  • Lasix Special
  • Laxur
  • Lazix
  • Leodrine
  • Less Diur
  • Liside
  • Logirene
  • Lowpston
  • Lowpstron
  • Luscek
  • Macasirool
  • Marsemide
  • Mirfat
  • Mita
  • Moilarorin
  • Myrosemide
  • Nadis
  • Nelsix
  • Neo-Renal
  • Novosemide
  • Octan Draselny
  • Odemase
  • Odemex
  • Oedemex
  • Olmagran
  • Polysquall A
  • Prefemin
  • Profemin
  • Promedes
  • Promide
  • Protargen
  • Puresis
  • Radisemide
  • Radonna
  • Radouna
  • Retep
  • Rodiuran
  • Rontyl
  • Rosemide
  • Rosis
  • Rusyde
  • Sal Diureticum
  • Salinex
  • Salix
  • Salurex
  • Salurid
  • Saluron
  • Seguril
  • Selectofur
  • Sigasalur
  • Sisuril
  • Spirofur
  • Synephron
  • Transit
  • Trofurit
  • Uremide
  • Uresix
  • Urex
  • Urex-M
  • Urian
  • Uridon
  • Uritol
  • Urosemide
  • Vergonil
  • Vesix
  • Yidoli
  • Zafimida
Brand name mixtures Not Available
Categories
  • Diuretics
  • Sodium Potassium Chloride Symporter Inhibitors
CAS number 54-31-9
Weight Average: 330.744
Monoisotopic: 330.007719869
Chemical Formula C12H11ClN2O5S
InChI Key InChIKey=ZZUFCTLCJUWOSV-UHFFFAOYSA-N
InChI
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)
Plain Text
IUPAC Name
4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoic acid
SMILES
NS(=O)(=O)C1=CC(C(O)=O)=C(NCC2=CC=CO2)C=C1Cl
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Aminobenzoates
  • Benzenesulfonamides
  • Sulfanilamides
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Benzoates
  • Aliphatic and Aryl Amines
  • Sulfonyls
  • Benzene and Derivatives
  • Aminobenzoates
  • Aryl Halides
  • Benzenesulfonamides
  • Halobenzenes
  • Carboxylic Acids and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Sulfanilamides
  • Sulfonamides
  • Furans
  • Benzoyl Derivatives
  • Anilines
Pharmacology
Indication For the treatment of edema associated with congestive heart failure, cirrhosis of the liver, and renal disease, including the nephrotic syndrome. Also for the treatment of hypertension alone or in combination with other antihypertensive agents.
Pharmacodynamics Furosemide, a sulfonamide-type loop diuretic structurally related to bumetanide, is used to manage hypertension and edema associated with congestive heart failure, cirrhosis, and renal disease, including the nephrotic syndrome.
Mechanism of action Furosemide, a loop diuretic, inhibits water reabsorption in the nephron by blocking the sodium-potassium-chloride cotransporter (NKCC2) in the thick ascending limb of the loop of Henle. This is achieved through competitive inhibition at the chloride binding site on the cotransporter, thus preventing the transport of sodium from the lumen of the loop of Henle into the basolateral interstitium. Consequently, the lumen becomes more hypertonic while the interstitium becomes less hypertonic, which in turn diminishes the osmotic gradient for water reabsorption throughout the nephron. Because the thick ascending limb is responsible for 25% of sodium reabsorption in the nephron, furosemide is a very potent diuretic.
Absorption 60% absorbed in patients with normal renal function
Volume of distribution Not Available
Protein binding 95% bound to plasma proteins
Metabolism

Only a small amount is hepatically metabolized to the defurfurylated derivative, 4-chloro-5-sulfamoylanthranilic acid.
Route of elimination Furosemide is excreted in urine. Significantly more furosemide is excreted in urine following the I.V. injection than after the tablet or oral solution.
Half life 2 hours
Clearance Not Available
Toxicity Profound diuresis may cause fluid and electrolyte depletion. Excessive dehydration and potassium depletion may occur. Excessive diuresis may cause rapid weight loss, orthostatic hypotension or acute hypotensive episodes. May also cause tinnitus, reversible or permanent hearing loss or reversible deafness.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00115 Furosemide Pathway SMP00115
Pharmacoeconomics
Manufacturers
  • Abraxis pharmaceutical products
  • App pharmaceuticals llc
  • Astrazeneca lp
  • Baxter healthcare corp anesthesia and critical care
  • Hospira inc
  • International medication system
  • Luitpold pharmaceuticals inc
  • Marsam pharmaceuticals llc
  • Organon usa inc
  • Smith and nephew solopak div smith and nephew
  • Warner chilcott div warner lambert co
  • Watson laboratories inc
  • Wockhardt ltd
  • Wyeth ayerst laboratories
  • Sanofi aventis us llc
  • Roxane laboratories inc
  • Wockhardt eu operations (swiss) ag
  • Dava pharmaceuticals inc
  • Excellium pharmaceutical inc
  • International medication systems ltd
  • Ipca laboratories ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Kalapharm inc
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Superpharm corp
  • Vintage pharmaceuticals inc
  • County line pharmaceuticals llc
Packagers
Dosage forms
Form Route Strength
Liquid Intramuscular
Solution Intravenous
Solution Oral
Tablet Oral
Prices
Unit description Cost Unit
Hydro 40 40% Foam 150 gm Can 182.52 USD can
Hydro 40 40% Foam 70 gm Can 148.99 USD can
Furosemide 10 mg/ml Solution 60ml Bottle 17.99 USD bottle
Furosemide 10 mg/ml Solution 120ml Bottle 15.98 USD bottle
Furosemide powder 3.51 USD g
Lasix Special 500 mg Tablet 3.25 USD tablet
Urex 1 gm tablet 2.47 USD tablet
Furosemide 10 mg/ml cartrg 1.45 USD ml
Lasix 80 mg tablet 1.0 USD tablet
Furosemide 10 mg/ml Solution 0.9 USD ml
Furosemide 10 mg/ml 0.75 USD ml
Lasix 40 mg tablet 0.53 USD tablet
Furosemide 80 mg tablet 0.45 USD tablet
Lasix 20 mg tablet 0.42 USD tablet
Lasix 10 mg/ml Solution 0.3 USD ml
CVS Pharmacy diuretic 50 mg softgel 0.17 USD softgel capsule
Furosemide 40 mg tablet 0.16 USD tablet
Furosemide 20 mg tablet 0.14 USD tablet
Apo-Furosemide 80 mg Tablet 0.13 USD tablet
Novo-Semide 80 mg Tablet 0.13 USD tablet
Nat herbal diuretic tablet sa 0.1 USD tablet
Apo-Furosemide 40 mg Tablet 0.07 USD tablet
Natural herbal diuretic tablet 0.07 USD tablet
Novo-Semide 40 mg Tablet 0.07 USD tablet
Apo-Furosemide 20 mg Tablet 0.05 USD tablet
Novo-Semide 20 mg Tablet 0.05 USD tablet
Patents Not Available
Properties
State solid
Melting point 206 oC
Experimental Properties
Property Value Source
water solubility 0.006 mg/mL PhysProp
logP 1.4 PhysProp
logS -3.66 [ADME Research, USCD] PhysProp
Caco2 permeability -6.5 [ADME Research, USCD] BiGG
Predicted Properties
Property Value Source
water solubility 1.18e-01 g/l ALOGPS
logP 2.71 ALOGPS
logP 1.75 ChemAxon Molconvert
logS -3.45 ALOGPS
pKa 9.83 ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 122.63 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 77.47 ChemAxon Molconvert
polarizability 30.55 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Rais-Bahrami K, Majd M, Veszelovszky E, Short BL: Use of furosemide and hearing loss in neonatal intensive care survivors. Am J Perinatol. 2004 Aug;21(6):329-32. Pubmed
  2. Korpi ER, Kuner T, Seeburg PH, Luddens H: Selective antagonist for the cerebellar granule cell-specific gamma-aminobutyric acid type A receptor. Mol Pharmacol. 1995 Feb;47(2):283-9. Pubmed
  3. Tia S, Wang JF, Kotchabhakdi N, Vicini S: Developmental changes of inhibitory synaptic currents in cerebellar granule neurons: role of GABA receptor alpha 6 subunit. J Neurosci. 1996 Jun 1;16(11):3630-40. Pubmed
  4. Wafford KA, Thompson SA, Thomas D, Sikela J, Wilcox AS, Whiting PJ: Functional characterization of human gamma-aminobutyric acidA receptors containing the alpha 4 subunit. Mol Pharmacol. 1996 Sep;50(3):670-8. Pubmed
External Links
Resource Link
KEGG Drug D00331 Link_out
PubChem Compound 3440 Link_out
PubChem Substance 46506779 Link_out
ChemSpider 3322 Link_out
BindingDB 25902 Link_out
ChEBI 47426 Link_out
ChEMBL 47426 Link_out
Therapeutic Targets Database DAP000043 Link_out
PharmGKB PA449719 Link_out
HET FUN Link_out
Drug Product Database 2247372 Link_out
RxList http://www.rxlist.com/cgi/generic/furos.htm Link_out
Drugs.com http://www.drugs.com/furosemide.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Furosemide Link_out
ATC Codes
  • C03CA01
AHFS Codes
  • 40:28.08
PDB Entries Not Available
FDA label show (461.7 KB)
MSDS show (74.3 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Avoid excess salt/sodium unless otherwise instructed by your physician.
  • Increase potassium intake; add a banana or orange juice; unless instructed otherwise.
  • Take with food to reduce irritation.
Targets

1. Solute carrier family 12 member 1

Pharmacological action: yes
Actions: inhibitor

Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume

Organism class: human
UniProt ID: Q13621 Link_out
Gene: SLC12A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Brater DC: Pharmacology of diuretics. Am J Med Sci. 2000 Jan;319(1):38-50. Pubmed
  2. Davies DL, Wilson GM: Diuretics: mechanism of action and clinical application. Drugs. 1975;9(3):178-226. Pubmed
  3. Vormfelde SV, Sehrt D, Toliat MR, Schirmer M, Meineke I, Tzvetkov M, Nurnberg P, Brockmoller J: Genetic variation in the renal sodium transporters NKCC2, NCC, and ENaC in relation to the effects of loop diuretic drugs. Clin Pharmacol Ther. 2007 Sep;82(3):300-9. Epub 2007 Apr 25. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Carbonic anhydrase 2

Pharmacological action: unknown

Reversible hydration of carbon dioxide

Organism class: human
UniProt ID: P00918 Link_out
Gene: CA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
Enzymes

1. 6-phosphogluconate dehydrogenase, decarboxylating

Actions: inhibitor

6-phospho-D-gluconate + NADP(+) = D-ribulose 5-phosphate + CO(2) + NADPH

UniProt ID: P52209 Link_out
Gene: PGD Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Akkemik E, Budak H, Ciftci M: Effects of some drugs on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro study. J Enzyme Inhib Med Chem. 2010 Mar 17. Pubmed
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor, inducer
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kim GH, Na KY, Kim SY, Joo KW, Oh YK, Chae SW, Endou H, Han JS: Up-regulation of organic anion transporter 1 protein is induced by chronic furosemide or hydrochlorothiazide infusion in rat kidney. Nephrol Dial Transplant. 2003 Aug;18(8):1505-11. Pubmed
  2. Hosoyamada M, Sekine T, Kanai Y, Endou H: Molecular cloning and functional expression of a multispecific organic anion transporter from human kidney. Am J Physiol. 1999 Jan;276(1 Pt 2):F122-8. Pubmed
  3. Lu R, Chan BS, Schuster VL: Cloning of the human kidney PAH transporter: narrow substrate specificity and regulation by protein kinase C. Am J Physiol. 1999 Feb;276(2 Pt 2):F295-303. Pubmed
  4. Uwai Y, Saito H, Hashimoto Y, Inui KI: Interaction and transport of thiazide diuretics, loop diuretics, and acetazolamide via rat renal organic anion transporter rOAT1. J Pharmacol Exp Ther. 2000 Oct;295(1):261-5. Pubmed

2. Organic cation/carnitine transporter 2

Actions: inhibitor

Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3

UniProt ID: O76082 Link_out
Gene: SLC22A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. Pubmed

3. Solute carrier family 22 member 8

Actions: inhibitor

Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA)

UniProt ID: Q8TCC7 Link_out
Gene: SLC22A8 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. Pubmed
  2. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. Pubmed

4. Canalicular multispecific organic anion transporter 1

Actions: inhibitor

Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter

UniProt ID: Q92887 Link_out
Gene: ABCC2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Bakos E, Evers R, Sinko E, Varadi A, Borst P, Sarkadi B: Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol Pharmacol. 2000 Apr;57(4):760-8. Pubmed

5. Solute carrier organic anion transporter family member 2A1

Actions: inhibitor

May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, as well as PGE1, PGE2 and PGF2A

UniProt ID: Q92959 Link_out
Gene: SLCO2A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL: Identification and characterization of a prostaglandin transporter. Science. 1995 May 12;268(5212):866-9. Pubmed

6. Solute carrier family 22 member 11

Actions: inhibitor

Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds

UniProt ID: Q9NSA0 Link_out
Gene: SLC22A11 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12. Pubmed
Carriers

1. Serum albumin

Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Lebedev AA, Samokrutova OV: [Study of the binding of diuretics by serum proteins according to changes in tryptophan fluorescence] Farmakol Toksikol. 1989 May-Jun;52(3):40-3. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on October 11, 2011 12:43

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.