U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H10ClN2O5S.Na
Molecular Weight 352.7275
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FUROSEMIDE SODIUM

SMILES

c1cc(CNc2cc(c(cc2C(=O)[O-])S(=O)(=O)N)Cl)oc1.[Na+]

InChI

InChIKey=DLFCAVBMDSKMEY-UHFFFAOYSA-M
InChI=1S/C12H11ClN2O5S.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula C12H10ClN2O5S
Molecular Weight 329.7377
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Curator's Comment:: furosemide did not cross the barrier

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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]
0.08 mM [IC50]
52.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LASIX

Approved Use

Edema 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 Use

Edema 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

Cmax

ValueDoseCo-administeredAnalytePopulation
1315.34 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
3014.77 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.1 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
3.2%
FUROSEMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
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
no
no
no
yes
yes
yes
yes
yes
yes
yes
yes
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

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Permanent deafness associated with furosemide administration.
1975 Jan-Feb
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
[A case of pulmonary tuberculosis with acute renal failure caused by readministration of rifampicin].
1999 Nov
Effect of thiazide on established furosemide-induced nephrocalcinosis in the young rat.
2000 Jan
Functional comparison of the K+-Cl- cotransporters KCC1 and KCC4.
2000 Sep 29
Release of furosemide from multiple-unit and single-unit preparations containing different viscosity grades of sodium alginate.
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
Furosemide-probenecid interaction as a laboratory exercise for undergraduate education in clinical pharmacology.
2001 Apr
Systemic sclerosis (scleroderma). A case of recovery of cardiomyopathy after vitamin E treatment.
2001 Apr
Renal concentrating defect in mice lacking group IV cytosolic phospholipase A(2).
2001 Apr
Alternatively spliced isoform of apical Na(+)-K(+)-Cl(-) cotransporter gene encodes a furosemide-sensitive Na(+)-Cl(-)cotransporter.
2001 Apr
Distinguishing cochlear pathophysiology in 4-aminopyridine and furosemide treated ears using a nonlinear systems identification technique.
2001 Feb
Brown Norway chromosome 13 confers protection from high salt to consomic Dahl S rat.
2001 Feb
Mechanisms of chloride transport in thymic lymphocytes.
2001 Feb
Activation of Na(+), K(+), Cl(-)-cotransport mediates intracellular Ca(2+) increase and apoptosis induced by Pinacidil in HepG2 human hepatoblastoma cells.
2001 Feb 23
Acute congestive heart failure associated with a limited form of systemic sclerosis and primary biliary cirrhosis.
2001 Jan
Renal follow up of premature infants with and without perinatal indomethacin exposure.
2001 Jan
Furosemide-induced natriuresis as a test to identify cirrhotic patients with refractory ascites.
2001 Jan
Effects of PMCA2 mutation on DPOAE amplitudes and latencies in deafwaddler mice.
2001 Jan
[Rhabdomyolysis as a rare complication of theophylline poisoning].
2001 Jan 15
[Life threatening hypercalcemia in a young man with ALL].
2001 Jan 5
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
Perturbation of the pump-leak balance for Na(+) and K(+) in malaria-infected erythrocytes.
2001 Jun
Haemoconcentration, shear-stress increase and carotid artery diameter regulation after furosemide administration in older hypertensives.
2001 Mar
Optical imaging reveals cation--Cl(-) cotransporter-mediated transient rapid decrease in intracellular Cl(-) concentration induced by oxygen--glucose deprivation in rat neocortical slices.
2001 Mar
Aggressive diuresis for severe heart failure in the elderly.
2001 Mar
Intraplatelet calcium levels in patients with acute renal failure before and after the administration of loop diuretics.
2001 Mar
[Extrarenal effects of furosemide on normal and ischemic cerebral tissue in the rat].
2001 Mar 1-15
Natriuresis and "dilutional" hyponatremia after infusion of glycine 1.5%.
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
Nephrocalcinosis induced by furosemide in an adult patient with incomplete renal tubular acidosis.
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
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
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:12:16 UTC 2021
Edited
by admin
on Sat Jun 26 14:12:16 UTC 2021
Record UNII
101EM454S7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FUROSEMIDE SODIUM
WHO-DD  
Common Name English
FUROSEMIDE SODIUM [WHO-DD]
Common Name English
SODIUM FUROSEMIDE
Common Name English
SODIUM 4-CHLORO-2-(2-FURYLMETHYLAMINO)-5-SULFAMOYL-BENZOATE
Systematic Name English
Code System Code Type Description
CAS
41733-55-5
Created by admin on Sat Jun 26 14:12:17 UTC 2021 , Edited by admin on Sat Jun 26 14:12:17 UTC 2021
PRIMARY
ECHA (EC/EINECS)
255-526-5
Created by admin on Sat Jun 26 14:12:17 UTC 2021 , Edited by admin on Sat Jun 26 14:12:17 UTC 2021
PRIMARY
EVMPD
SUB02287MIG
Created by admin on Sat Jun 26 14:12:17 UTC 2021 , Edited by admin on Sat Jun 26 14:12:17 UTC 2021
PRIMARY
EPA CompTox
41733-55-5
Created by admin on Sat Jun 26 14:12:17 UTC 2021 , Edited by admin on Sat Jun 26 14:12:17 UTC 2021
PRIMARY
FDA UNII
101EM454S7
Created by admin on Sat Jun 26 14:12:17 UTC 2021 , Edited by admin on Sat Jun 26 14:12:17 UTC 2021
PRIMARY
PUBCHEM
23673593
Created by admin on Sat Jun 26 14:12:17 UTC 2021 , Edited by admin on Sat Jun 26 14:12:17 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY