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Details

Stereochemistry ACHIRAL
Molecular Formula C12H11ClN2O5S
Molecular Weight 330.7456
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FUROSEMIDE

SMILES

c1cc(CNc2cc(c(cc2C(=O)O)S(=O)(=O)N)Cl)oc1

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)

HIDE SMILES / InChI

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
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
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
Statistical evaluation of the regulatory guidelines for use of furosemide in race horses.
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
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.
Name Type Language
FUROSEMIDE
EP   GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
5-(AMINOSULFONYL)-4-CHLORO-2-((2-FURYLMETHYL)AMINO)BENZOIC ACID
Systematic Name English
BENZOIC ACID, 5-(AMINOSULFONYL)-4-CHLORO-2-((2-FURANYLMETHYL)AMINO)-
Common Name English
LOGIRENE
Brand Name English
FUROSEMIDE [IARC]
Common Name English
FUROSEMIDE [ORANGE BOOK]
Common Name English
FUROSEMIDE [EP MONOGRAPH]
Common Name English
FUROSEMIDE [WHO-IP]
Common Name English
FUROSEMIDE [VANDF]
Common Name English
LB-502
Code English
OEDEMEX
Common Name English
FUROSEMIDUM [WHO-IP LATIN]
Common Name English
FUROSEMIDE [USP MONOGRAPH]
Common Name English
FRUSEMIDE
Common Name English
FUROSEMIDE [GREEN BOOK]
Common Name English
MARSEMIDE
Common Name English
FUROSEMIDE [INN]
Common Name English
LASIX
Brand Name English
MIRFAT
Brand Name English
4-CHLORO-N-FURFURYL-5-SULFAMOYLANTHRANILIC ACID
Systematic Name English
NSC-269420
Code English
FUROSEMIDE [WHO-DD]
Common Name English
FUROSEMIDE [MART.]
Common Name English
FUROSEMIDE [MI]
Common Name English
FUROSEMIDE [HSDB]
Common Name English
FUROSEMIDE [USAN]
Common Name English
FUROSEMIDE [USP-RS]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 12.4
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
CFR 21 CFR 522.1010
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
NDF-RT N0000175590
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
WHO-VATC QC03CB01
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
WHO-ATC C03EB01
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
LIVERTOX 445
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
NCI_THESAURUS C49184
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
WHO-VATC QC03EB01
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 16
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
WHO-ATC C03CA01
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
NDF-RT N0000175366
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
WHO-ATC C03CB01
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
CFR 21 CFR 520.1010
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
WHO-VATC QC03CA01
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
Code System Code Type Description
IUPHAR
4839
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
ChEMBL
CHEMBL35
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
RXCUI
4603
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
FUROSEMIDE
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
USP_CATALOG
1287008
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY USP-RS
FDA UNII
7LXU5N7ZO5
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
MESH
D005665
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-203-6
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
EPA CompTox
54-31-9
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
DRUG BANK
DB00695
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
MERCK INDEX
M5608
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY Merck Index
WHO INTERNATIONAL PHARMACOPEIA
FUROSEMIDE
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
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.
CAS
54-31-9
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
NCI_THESAURUS
C515
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
LACTMED
Furosemide
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
HSDB
3086
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
PUBCHEM
3440
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
INN
1584
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
DRUG CENTRAL
1258
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY
EVMPD
SUB07849MIG
Created by admin on Fri Jun 25 20:34:23 UTC 2021 , Edited by admin on Fri Jun 25 20:34:23 UTC 2021
PRIMARY