Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H11ClN2O5S |
Molecular Weight | 330.744 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NS(=O)(=O)C1=CC(C(O)=O)=C(NCC2=CC=CO2)C=C1Cl
InChI
InChIKey=ZZUFCTLCJUWOSV-UHFFFAOYSA-N
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)
DescriptionSources: http://www.drugbank.ca/drugs/DB00695Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/furosemide.html
Sources: http://www.drugbank.ca/drugs/DB00695
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/furosemide.html
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. Furosemide 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. Furosemide is sold under the brand name Lasix among others.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15356425
Curator's Comment: furosemide did not cross the barrier
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1874 Sources: http://www.drugbank.ca/drugs/DB00695 |
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Target ID: P05370 Gene ID: 24377.0 Gene Symbol: G6pdx Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26758606 |
0.13 mM [IC50] | ||
Target ID: P85968 Gene ID: 1.00360176E8 Gene Symbol: Pgd Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26758606 |
0.14 mM [IC50] | ||
Target ID: CHEMBL3286088 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26758606 |
0.08 mM [IC50] | ||
Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10713865 |
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Target ID: CHEMBL3510 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19119014 |
52.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LASIX Approved UseEdema
Furosemide is indicated in adults and pediatric patients for the treatment of edema associated with congestive heart failure, cirrhosis of the liver, and renal disease, including the nephrotic syndrome. Furosemide is particularly useful when an agent with greater diuretic potential is desired.
Hypertension
Oral Furosemide may be used in adults for the treatment of hypertension alone or in combination with other antihypertensive agents. Launch Date1966 |
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Primary | LASIX Approved UseEdema
Furosemide is indicated in adults and pediatric patients for the treatment of edema associated with congestive heart failure, cirrhosis of the liver, and renal disease, including the nephrotic syndrome. Furosemide is particularly useful when an agent with greater diuretic potential is desired.
Hypertension
Oral Furosemide may be used in adults for the treatment of hypertension alone or in combination with other antihypertensive agents. Launch Date1966 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1315.34 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12854359 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
FUROSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3014.77 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12854359 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
FUROSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12854359 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
FUROSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.2% |
FUROSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
major | |||
Page: 9.0 |
major | yes (co-administration study) Comment: probe drug substrate for renal transporters OAT1 and OAT3; clinical investigation of a probe drug cocktail containing substrates of key drug transporters (digoxin, furosemide, metformin and rosuvastatin) Page: 9.0 |
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Page: 9.0 |
major | yes (co-administration study) Comment: probe drug substrate for renal transporters OAT1 and OAT3; clinical investigation of a probe drug cocktail containing substrates of key drug transporters (digoxin, furosemide, metformin and rosuvastatin) Page: 9.0 |
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Sources: https://pubmed.ncbi.nlm.nih.gov/11948555/ Page: 6.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11948555/ Page: 6.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11948555/ Page: 6.0 |
no | |||
Page: 6.0 |
yes | |||
Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18541222/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19126296/ Page: 1.0 |
yes | yes (co-administration study) Comment: The time-averaged non-renal clearance (CLNR) of furosemide tended to be faster (but not significantly so) among smokers (3-methylcholanthrene (3-MC) type; a main inducer of CYP1A1/2 Sources: https://pubmed.ncbi.nlm.nih.gov/19126296/ Page: 1.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15950494/ Page: 8.0 |
PubMed
Title | Date | PubMed |
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[A case of pulmonary tuberculosis with acute renal failure caused by readministration of rifampicin]. | 1999 Nov |
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Co-administration of furosemide augments tacrolimus-induced impairment in kidney function in rats. | 2000 |
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Persistent nephrocalcinosis for acetazolamide and furosemide in a pediatric patient. | 2000 Nov |
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Influence of the M235T polymorphism of human angiotensinogen (AGT) on plasma AGT and renin concentrations after ethinylestradiol administration. | 2000 Nov |
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Endogenous bradykinin and the renin and pressor responses to furosemide in humans. | 2000 Nov |
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Functional comparison of the K+-Cl- cotransporters KCC1 and KCC4. | 2000 Sep 29 |
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Should celecoxib be contraindicated in patients who are allergic to sulfonamides? Revisiting the meaning of 'sulfa' allergy. | 2001 |
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Release of furosemide from multiple-unit and single-unit preparations containing different viscosity grades of sodium alginate. | 2001 |
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Diuretic-enhanced gadolinium excretory MR urography: comparison of conventional gradient-echo sequences and echo-planar imaging. | 2001 |
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Maxi K+ channels co-localised with CFTR in the apical membrane of an exocrine gland acinus: possible involvement in secretion. | 2001 Apr |
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Effect of salicis cortex extract on human platelet aggregation. | 2001 Apr |
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Furosemide-probenecid interaction as a laboratory exercise for undergraduate education in clinical pharmacology. | 2001 Apr |
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Pressure-independent enhancement of cardiac hypertrophy in natriuretic peptide receptor A-deficient mice. | 2001 Apr |
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Aspirin inhibits the acute venodilator response to furosemide in patients with chronic heart failure. | 2001 Apr |
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ATP stimulates calcium-dependent glutamate release from cultured astrocytes. | 2001 Apr |
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Chronic tubulointerstitial nephritis and distal renal tubular acidosis in a patient with frusemide abuse. | 2001 Apr |
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Deterioration of left ventricular chamber performance after bed rest : "cardiovascular deconditioning" or hypovolemia? | 2001 Apr 10 |
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Renal interstitial atp responses to changes in arterial pressure during alterations in tubuloglomerular feedback activity. | 2001 Feb |
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Brown Norway chromosome 13 confers protection from high salt to consomic Dahl S rat. | 2001 Feb |
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Effect of furosemide on renal excretion of oxypurinol and purine bases. | 2001 Feb |
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Hyponatremia and sensorineural hearing loss in preterm infants. | 2001 Feb |
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Congestive heart failure associated with myxomatous degeneration of the left atrioventricular valve in a parakeet. | 2001 Feb 1 |
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Self-retaining aural speculum: a valuable aid to middle-ear surgery. | 2001 Jan |
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10% hydroxyethyl starch for plasma expansion in the treatment of severe ovarian hyperstimulation syndrome. A case report. | 2001 Jan |
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Acute congestive heart failure associated with a limited form of systemic sclerosis and primary biliary cirrhosis. | 2001 Jan |
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Renal cortical scintigraphy and diuresis renography in infants and children. | 2001 Jan |
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Fluorodeoxyglucose positron emission tomography studies in diagnosis and staging of clinically organ-confined prostate cancer. | 2001 Jan |
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Prehospital management of rapid atrial fibrillation: recommendations for treatment protocols. | 2001 Jan |
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Effects of PMCA2 mutation on DPOAE amplitudes and latencies in deafwaddler mice. | 2001 Jan |
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[Rhabdomyolysis as a rare complication of theophylline poisoning]. | 2001 Jan 15 |
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Pamidronate and calcitonin as therapy of acute cancer-related hypercalcemia in children. | 2001 Jan-Feb |
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The intracellular localization of the mineralocorticoid receptor is regulated by 11beta-hydroxysteroid dehydrogenase type 2. | 2001 Jul 27 |
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Angiotensin converting enzyme inhibition worsens the excretory phase of diuretic renography for obstructive hydronephrosis. | 2001 Jun |
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Perturbation of the pump-leak balance for Na(+) and K(+) in malaria-infected erythrocytes. | 2001 Jun |
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Long-term efficacy of torsemide compared with frusemide in cirrhotic patients with ascites. | 2001 Mar |
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The appropriateness of drug use in an older nondemented and demented population. | 2001 Mar |
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Humoral hypercalcemia of malignancy in squamous cell carcinoma of the skin: parathyroid hormone--related protein as a cause. | 2001 Mar |
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Effect of furosemide on basal lamina anionic sites in guinea pig labyrinth. | 2001 Mar |
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Homogeneous enzyme immunoassay for triiodothyronine in serum. | 2001 Mar |
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Role of diuretics in the preservation of residual renal function in patients on continuous ambulatory peritoneal dialysis. | 2001 Mar |
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Effects of inhalation of albuterol sulphate, ipratroprium bromide and frusemide on breathing mechanics and gas exchange in healthy exercising horses. | 2001 May |
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Diamidine compounds: selective uptake and targeting in Plasmodium falciparum. | 2001 May |
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Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
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Ethanol-induced swelling in neonatal rat primary astrocyte cultures. | 2001 May 11 |
Patents
Sample Use Guides
The usual initial dose of LASIX is 20 to 80 mg given as a single dose. Ordinarily a prompt diuresis ensues. If needed, the same dose can be administered 6 to 8 hours later or the dose may be increased. The dose may be raised by 20 or 40 mg and given not sooner than 6 to 8 hours after the previous dose until the desired diuretic effect has been obtained. The individually determined single dose should then be given once or twice daily (eg, at 8 am and 2 pm). The dose of LASIX may be carefully titrated up to 600 mg/day in patients with clinically severe edematous states.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10619350
There was a significant reduction in levels of TNF-alpha and IL-6 at a furosemide concentration of 0.5 x 10(-2) M and a reduction in IL-8 levels at 10(-2) M in human peripheral blood mononuclear cells.
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Classification Tree | Code System | Code | ||
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WHO-ESSENTIAL MEDICINES LIST |
12.4
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CFR |
21 CFR 522.1010
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NDF-RT |
N0000175590
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WHO-VATC |
QC03CB01
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WHO-ATC |
C03EB01
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LIVERTOX |
445
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NCI_THESAURUS |
C49184
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WHO-VATC |
QC03EB01
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16
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C03CA01
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N0000175366
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C03CB01
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CFR |
21 CFR 520.1010
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WHO-VATC |
QC03CA01
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4839
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CHEMBL35
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4603
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FUROSEMIDE
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47426
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1287008
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DTXSID6020648
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DB00695
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m5608
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100000090317
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FUROSEMIDE
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PRIMARY | Description: A white or almost white, crystalline powder; odourless. Solubility: Practically insoluble in water; soluble in 75 parts of ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Diuretic. Storage: Furosemide should be kept in a well-closed container, protected from light. Definition: Furosemide contains not less than 98.0% and not more than 101.0% of C12H11ClN2O5S, calculated with reference to the dried substance. | ||
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54-31-9
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C515
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Furosemide
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3086
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7LXU5N7ZO5
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1584
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1258
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SUB07849MIG
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)