CHEBI:47426 - furosemide

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name furosemide
ChEBI ID CHEBI:47426
Definition A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:47425, CHEBI:5198
Supplier Information ChemicalBook:CB2724915, eMolecules:509860, ZINC000000097471
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Venlafaxine, sold under the brand name Effexor among others, is an antidepressant medication of the serotonin–norepinephrine reuptake inhibitor (SNRI) class. It is used to treat major depressive disorder, generalized anxiety disorder, panic disorder, and social anxiety disorder. Studies have shown that venlafaxine improves post-traumatic stress disorder (PTSD). It may also be used for chronic neuropathic pain. It is taken orally (swallowed by mouth). It is also available as the salt venlafaxine besylate (venlafaxine benzenesulfonate monohydrate) in an extended-release formulation (Venbysi XR). Common side effects include loss of appetite, constipation, dry mouth, dizziness, sweating, insomnia, drowsiness and sexual problems. Severe side effects include an increased risk of suicide, mania, and serotonin syndrome. Antidepressant withdrawal syndrome may occur if stopped. There are concerns that use during the later part of pregnancy can harm the baby. How it works is not entirely clear, but it seems to be related to the potentiation of the activity of some neurotransmitters in the brain. Venlafaxine was approved for medical use in the United States in 1993. It is available as a generic medication. In 2022, it was the 44th most commonly prescribed medication in the United States, with more than 13 million prescriptions.
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Formula C12H11ClN2O5S
Net Charge 0
Average Mass 330.74400
Monoisotopic Mass 330.00772
InChI 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)
InChIKey ZZUFCTLCJUWOSV-UHFFFAOYSA-N
SMILES NS(=O)(=O)c1cc(C(O)=O)c(NCc2ccco2)cc1Cl
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): loop diuretic
A diuretic that acts on the ascending loop of Henle in the kidney.
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ChEBI Ontology
Outgoing furosemide (CHEBI:47426) has role environmental contaminant (CHEBI:78298)
furosemide (CHEBI:47426) has role loop diuretic (CHEBI:77608)
furosemide (CHEBI:47426) has role xenobiotic (CHEBI:35703)
furosemide (CHEBI:47426) is a chlorobenzoic acid (CHEBI:23134)
furosemide (CHEBI:47426) is a furans (CHEBI:24129)
furosemide (CHEBI:47426) is a sulfonamide (CHEBI:35358)
IUPAC Name
4-chloro-2-{[(furan-2-yl)methyl]amino}-5-sulfamoylbenzoic acid
Synonyms Sources
2-Furfurylamino-4-chloro-5-sulfamoylbenzoic acid ChemIDplus
4-Chloro-5-sulfamoyl-N-furfuryl-anthranilic acid ChemIDplus
4-Chloro-N-(2-furylmethyl)-5-sulfamoylanthranilic acid ChemIDplus
4-Chloro-N-furfuryl-5-sulfamoylanthranilic acid ChemIDplus
Frusemide KEGG DRUG
Furosemide KEGG DRUG
Lasix (TN) KEGG DRUG
Manual Xrefs Databases
1258 DrugCentral
1770 VSDB
D00331 KEGG DRUG
DB00695 DrugBank
Furosemide Wikipedia
HMDB0001933 HMDB
LSM-5847 LINCS
View more database links
Registry Numbers Types Sources
1399731 Reaxys Registry Number Reaxys
54-31-9 CAS Registry Number ChemIDplus
54-31-9 CAS Registry Number KEGG DRUG
Citations Types Sources
15286542 PubMed citation Europe PMC
18701232 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag