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

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
Structure of FUROSEMIDE

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)

HIDE SMILES / InChI

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

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

1966
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

1966
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
Nephrocalcinosis in full-term infants receiving furosemide treatment for congestive heart failure: a study of the incidence and 2-year follow up.
1999 Aug
Acetazolamide and furosemide for posthemorrhagic hydrocephalus of the newborn.
1999 Mar
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
Activation of renal afferent pathways following furosemide treatment. I. Effects Of survival time and renal denervation.
2000 Apr 10
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.
2000 Feb 11
Persistent nephrocalcinosis for acetazolamide and furosemide in a pediatric patient.
2000 Nov
Influence of the M235T polymorphism of human angiotensinogen (AGT) on plasma AGT and renin concentrations after ethinylestradiol administration.
2000 Nov
Release of furosemide from multiple-unit and single-unit preparations containing different viscosity grades of sodium alginate.
2001
Diuretic-enhanced gadolinium excretory MR urography: comparison of conventional gradient-echo sequences and echo-planar imaging.
2001
Maxi K+ channels co-localised with CFTR in the apical membrane of an exocrine gland acinus: possible involvement in secretion.
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
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
Role of the renal kallikrein-kinin system in the development of salt-sensitive hypertension.
2001 Jan
Renal cortical scintigraphy and diuresis renography in infants and children.
2001 Jan
Furosemide stimulates macula densa cyclooxygenase-2 expression in rats.
2001 Jan
Renal follow up of premature infants with and without perinatal indomethacin exposure.
2001 Jan
[Rhabdomyolysis as a rare complication of theophylline poisoning].
2001 Jan 15
Pamidronate and calcitonin as therapy of acute cancer-related hypercalcemia in children.
2001 Jan-Feb
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
Pediatric renal transplantation: anesthesia and perioperative complications.
2001 Mar
The appropriateness of drug use in an older nondemented and demented population.
2001 Mar
Statistical evaluation of the regulatory guidelines for use of furosemide in race horses.
2001 Mar
Aggressive diuresis for severe heart failure in the elderly.
2001 Mar
Role of diuretics in the preservation of residual renal function in patients on continuous ambulatory peritoneal dialysis.
2001 Mar
[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
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:07:40 GMT 2023
Edited
by admin
on Fri Dec 15 15:07:40 GMT 2023
Record UNII
7LXU5N7ZO5
Record Status Validated (UNII)
Record Version
  • Download
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
Furosemide [WHO-DD]
Common 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
FUROSCIX
Brand Name English
LB-502
Code English
OEDEMEX
Common Name English
FUROSEMIDE [JAN]
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 [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 Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
CFR 21 CFR 522.1010
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
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
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 16
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WHO-ATC C03CA01
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NDF-RT N0000175366
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
WHO-ATC C03CB01
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
CFR 21 CFR 520.1010
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
WHO-VATC QC03CA01
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
Code System Code Type Description
IUPHAR
4839
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PRIMARY
ChEMBL
CHEMBL35
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PRIMARY
RXCUI
4603
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
FUROSEMIDE
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY
CHEBI
47426
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PRIMARY
FDA UNII
7LXU5N7ZO5
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PRIMARY
MESH
D005665
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PRIMARY
ECHA (EC/EINECS)
200-203-6
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PRIMARY
NSC
269420
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PRIMARY
RS_ITEM_NUM
1287008
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PRIMARY
EPA CompTox
DTXSID6020648
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PRIMARY
DRUG BANK
DB00695
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PRIMARY
MERCK INDEX
m5608
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PRIMARY Merck Index
SMS_ID
100000090317
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
FUROSEMIDE
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
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 Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY
NCI_THESAURUS
C515
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PRIMARY
LACTMED
Furosemide
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PRIMARY
HSDB
3086
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PRIMARY
PUBCHEM
3440
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PRIMARY
DAILYMED
7LXU5N7ZO5
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY
INN
1584
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PRIMARY
DRUG CENTRAL
1258
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PRIMARY
EVMPD
SUB07849MIG
Created by admin on Fri Dec 15 15:07:40 GMT 2023 , Edited by admin on Fri Dec 15 15:07:40 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
POTENCY
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
MAJOR
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 2.0
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
ORAL BIOAVAILABILITY PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
MAXIMUM TOLERATED DOSE TOXICITY
Tmax PHARMACOKINETIC ORAL SOLUTION
PHARMACOKINETIC
SL TABLET
PHARMACOKINETIC
ORAL TABLET
PHARMACOKINETIC