Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H11ClN2O5S.C6H15NO |
| Molecular Weight | 447.934 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)CCO.NS(=O)(=O)C1=CC(C(O)=O)=C(NCC2=CC=CO2)C=C1Cl
InChI
InChIKey=JTMYQHVUVVWDOK-UHFFFAOYSA-N
InChI=1S/C12H11ClN2O5S.C6H15NO/c13-9-5-10(15-6-7-2-1-3-20-7)8(12(16)17)4-11(9)21(14,18)19;1-3-7(4-2)5-6-8/h1-5,15H,6H2,(H,16,17)(H2,14,18,19);8H,3-6H2,1-2H3
| Molecular Formula | C12H11ClN2O5S |
| Molecular Weight | 330.744 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C6H15NO |
| Molecular Weight | 117.1894 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1874 Sources: http://www.drugbank.ca/drugs/DB00695 |
|||
Target ID: P05370 Gene ID: 24377.0 Gene Symbol: G6pdx Target Organism: Rattus norvegicus (Rat) |
0.13 mM [IC50] | ||
Target ID: P85968 Gene ID: 1.00360176E8 Gene Symbol: Pgd Target Organism: Rattus norvegicus (Rat) |
0.14 mM [IC50] | ||
Target ID: CHEMBL3286088 |
0.08 mM [IC50] | ||
Target ID: CHEMBL261 |
|||
Target ID: CHEMBL3510 |
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 Date-1.10678401E11 |
|||
| 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 Date-1.10678401E11 |
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 |
|---|---|---|---|
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 1.0 |
major | |||
| 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 |
|||
| 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 |
|||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
| yes | ||||
| yes | ||||
Page: 1.0 |
yes | |||
Page: 1.0 |
yes | |||
Page: 1.0 |
yes | |||
Page: 1.0 |
yes | |||
Page: 1.0 |
yes | |||
Page: 1.0 |
yes | |||
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 Page: 1.0 |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 8.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The loop diuretic torasemide interferes with endothelin-1 actions in the aorta of hypertensive rats. | 2001 |
|
| Effects of loop diuretics on angiotensin II-stimulated vascular smooth muscle cell growth. | 2001 |
|
| Should celecoxib be contraindicated in patients who are allergic to sulfonamides? Revisiting the meaning of 'sulfa' allergy. | 2001 |
|
| Maxi K+ channels co-localised with CFTR in the apical membrane of an exocrine gland acinus: possible involvement in secretion. | 2001 Apr |
|
| Effect of salicis cortex extract on human platelet aggregation. | 2001 Apr |
|
| Improvement in site-specific intestinal absorption of furosemide by Eudragit L100-55. | 2001 Apr |
|
| Acute effects of the anti-inflammatory cyclooxygenase-2 selective inhibitor, flosulide, on renal plasma flow and glomerular filtration rate in rats. | 2001 Apr |
|
| Furosemide-probenecid interaction as a laboratory exercise for undergraduate education in clinical pharmacology. | 2001 Apr |
|
| Pressure-independent enhancement of cardiac hypertrophy in natriuretic peptide receptor A-deficient mice. | 2001 Apr |
|
| Aspirin inhibits the acute venodilator response to furosemide in patients with chronic heart failure. | 2001 Apr |
|
| ATP stimulates calcium-dependent glutamate release from cultured astrocytes. | 2001 Apr |
|
| Systemic sclerosis (scleroderma). A case of recovery of cardiomyopathy after vitamin E treatment. | 2001 Apr |
|
| Chronic tubulointerstitial nephritis and distal renal tubular acidosis in a patient with frusemide abuse. | 2001 Apr |
|
| Renal concentrating defect in mice lacking group IV cytosolic phospholipase A(2). | 2001 Apr |
|
| Deterioration of left ventricular chamber performance after bed rest : "cardiovascular deconditioning" or hypovolemia? | 2001 Apr 10 |
|
| Uptake mechanism of valproic acid in human placental choriocarcinoma cell line (BeWo). | 2001 Apr 13 |
|
| Towards evidence based emergency medicine: best BETs from the Manchester Royal Infirmary. Frusemide or nitrates in acute left ventricular failure. | 2001 Jan |
|
| Role of the renal kallikrein-kinin system in the development of salt-sensitive hypertension. | 2001 Jan |
|
| Sensitivity of synaptic GABA(A) receptors to allosteric modulators in hippocampal oriens-alveus interneurons. | 2001 Jul |
|
| The intracellular localization of the mineralocorticoid receptor is regulated by 11beta-hydroxysteroid dehydrogenase type 2. | 2001 Jul 27 |
|
| The effects of enalapril-digoxin-diuretic combination therapy on nutritional and anthropometric indices in chronic congestive heart failure: preliminary findings in cardiac cachexia. | 2001 Jun |
|
| Urolithiasis in the low birth weight infant: the role and efficacy of extracorporeal shock wave lithotripsy. | 2001 Jun |
|
| Angiotensin converting enzyme inhibition worsens the excretory phase of diuretic renography for obstructive hydronephrosis. | 2001 Jun |
|
| Supranormal differential renal function is real but may be pathological: assessment by 99m technetium mercaptoacetyltriglycine renal scan of congenital unilateral hydronephrosis. | 2001 Jun |
|
| Dynamic characteristics and underlying mechanisms of renal blood flow autoregulation in the conscious dog. | 2001 Jun |
|
| Perturbation of the pump-leak balance for Na(+) and K(+) in malaria-infected erythrocytes. | 2001 Jun |
|
| Pediatric renal transplantation: anesthesia and perioperative complications. | 2001 Mar |
|
| Long-term efficacy of torsemide compared with frusemide in cirrhotic patients with ascites. | 2001 Mar |
|
| The appropriateness of drug use in an older nondemented and demented population. | 2001 Mar |
|
| Multi-slice CT urography after diuretic injection: initial results. | 2001 Mar |
|
| Humoral hypercalcemia of malignancy in squamous cell carcinoma of the skin: parathyroid hormone--related protein as a cause. | 2001 Mar |
|
| Estimation of the probability for exceeding a threshold concentration of furosemide at various intervals after intravenous administration in horses. | 2001 Mar |
|
| Effect of furosemide on basal lamina anionic sites in guinea pig labyrinth. | 2001 Mar |
|
| Haemoconcentration, shear-stress increase and carotid artery diameter regulation after furosemide administration in older hypertensives. | 2001 Mar |
|
| [Extrarenal effects of furosemide on normal and ischemic cerebral tissue in the rat]. | 2001 Mar 1-15 |
|
| [Generalized edema following insulin treatment of newly diagnosed diabetes mellitus]. | 2001 Mar 20 |
|
| Natriuresis and "dilutional" hyponatremia after infusion of glycine 1.5%. | 2001 May |
|
| Taurocholic acid-induced secretion in normal and cystic fibrosis mouse ileum. | 2001 May |
|
| Pulmonary edema: new insight on pathogenesis and treatment. | 2001 May |
|
| Effects of inhalation of albuterol sulphate, ipratroprium bromide and frusemide on breathing mechanics and gas exchange in healthy exercising horses. | 2001 May |
|
| Long-term treatment of patients with inappropriate secretion of antidiuretic hormone by the vasopressin receptor antagonist conivaptan, urea, or furosemide. | 2001 May |
|
| Chloride channels regulate HIT cell volume but cannot fully account for swelling-induced insulin secretion. | 2001 May |
|
| Nephrocalcinosis induced by furosemide in an adult patient with incomplete renal tubular acidosis. | 2001 May |
|
| Effects of albumin/furosemide mixtures on responses to furosemide in hypoalbuminemic patients. | 2001 May |
|
| Diamidine compounds: selective uptake and targeting in Plasmodium falciparum. | 2001 May |
|
| Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
|
| Interaction of serotonin and cholecystokinin in the lateral parabrachial nucleus to control sodium intake. | 2001 May |
|
| Heterogeneous susceptibility of GABA(A) receptor-mediated IPSCs to depolarization-induced suppression of inhibition in rat hippocampus. | 2001 May 1 |
|
| Ethanol-induced swelling in neonatal rat primary astrocyte cultures. | 2001 May 11 |
|
| Fatal portal hypertension, liver failure, and mitochondrial dysfunction after HIV-1 nucleoside analogue-induced hepatitis and lactic acidaemia. | 2001 May 5 |
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
| Substance Class |
Chemical
Created
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| Record UNII |
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| Record Status |
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| Record Version |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |