Furosemide

Structural formula
General
Non-proprietary name	Furosemide
other names	4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid; IUPAC / Pharmacopoeia : 4-chloro-2 - [(furan-2-ylmethyl) amino] -5-sulfamoylbenzoic acid;
Molecular formula	C 12 H 11 ClN 2 O 5 S
External identifiers / databases
EC number	200-203-6
ECHA InfoCard	100,000.185
PubChem	3440
ChemSpider	3322
DrugBank	DB00695
Wikidata	Q388801
Drug information
ATC code	C03 CA01
Drug class	Loop diuretic
Mechanism of action	Inhibition of the Na + -K + -2Cl - symporter
properties
Molar mass	330.74 g mol −1
Physical state	firmly
Melting point	206 ° C
pK s value	3.8; 7.5
solubility	151 ± 7 mg l −1 (pH 4.5)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 360
	P: 201-308 + 313
Toxicological data	2600 mg kg −1 ( LD 50 , rat , oral ) ; 800 mg kg −1 ( LD 50 , rat , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Furosemide is a drug from the group of loop diuretics . Loop diuretics lead to the excretion of large volumes of tissue fluid by the kidney of the ascending part of Henle's loop a transport protein (the Na-K-2Cl cotransporters inhibit). If the drug is administered intravenously, excretion amounts of up to 50 liters per day are possible. It is a strong diuretic. Furosemide was patented by Hoechst in 1962 .

Chemical properties

When taken orally , furosemide is assigned to class IV in the biopharmaceutical classification system due to its poor solubility and poor permeability . The poor solubility is mainly due to the acid structure, which causes very poor solubility at low pH values . At a neutral pH value, furosemide is fairly soluble. The poor permeability is partly due to the affinity for an intestinal efflux pump , which has not yet been described in detail.

Analytics

For reliable qualitative and quantitative determination, after appropriate sample preparation, the coupling of gas chromatography or HPLC with mass spectrometry is used.

Indications

Approved indications are high blood pressure , ascites and edema (including cerebral edema ), for example due to heart failure or due to liver, kidney diseases or burns, and under certain circumstances also threatened kidney failure . Furosemide is also used in hyperkalemia to flush out excess potassium.

Furosemide is used as a masking agent in sport , as it helps to flush out any traces of doping agents that have been ingested from the body; it is therefore on the doping list.

Contraindications

Contraindications are: hypovolemia , anuria , hypokalaemia , use during breastfeeding and hepatic coma .

For side effects, see article loop diuretic .

Trade names

Monopreparations

Diurapid (D), Furanthril (D), Furobeta (D), Furodrix (CH), Furogamma (D), Furon (A), Furorese (D), Furosal (D), Fursol (CH), Fusid (D), Jufurix (D), Lasix (D, A, CH), Oedemex (CH), various generics (D, A, CH)

Combination preparations

Betasemid (D), Diaphal (D), Furorese comp (D), Furo-Spirobe (A), Furospir (CH), Lasilacton (A, CH), Lasitace (A), Osyrol-Lasix (D), Spiro comp ( D), Spiro-D (D)

Individual evidence

↑ ^a ^b ^c ^d Entry on furosemide. In: Römpp Online . Georg Thieme Verlag, accessed on June 24, 2014.
↑ K. Tsinman, A. Avdeef, O. Tsinman, D. Voloboy: Powder Dissolution Method for Estimating Rotating Disk Intrinsic Dissolution Rates of Low Solubility Drugs in Pharm Res 26 (2009) 2093-2100. doi : 10.1007 / s11095-009-9921-3 .
↑ ^a ^b Furosemide data sheet from Sigma-Aldrich , accessed on April 2, 2011 ( PDF ).

↑ Entry on furosemide in the ChemIDplus database of the United States National Library of Medicine (NLM) .

↑ Brunelli C, Bicchi C, Di Stilo A, Salomone A, Vincenti M: High-speed gas chromatography in doping control: fast-GC and fast-GC / MS determination of beta-adrenoceptor ligands and diuretics. , J Sep Sci. 2006 Dec; 29 (18): 2765-71, PMID 17305237

↑ Sora DI, Udrescu S, Albu F, David V, Medvedovici A: Analytical issues in HPLC / MS / MS simultaneous assay of furosemide, spironolactone and canrenone in human plasma samples. , J Pharm Biomed Anal. 2010 Sep 5; 52 (5): 734-40, PMID 20307949

↑ WADA : Doping List 2016 (PDF).

[Römpp-1] Entry on furosemide. In: Römpp Online . Georg Thieme Verlag, accessed on June 24, 2014.

[2] K. Tsinman, A. Avdeef, O. Tsinman, D. Voloboy: Powder Dissolution Method for Estimating Rotating Disk Intrinsic Dissolution Rates of Low Solubility Drugs in Pharm Res 26 (2009) 2093-2100. doi : 10.1007 / s11095-009-9921-3 .

[Sigma-3] Furosemide data sheet from Sigma-Aldrich , accessed on April 2, 2011 ( PDF ).

[ChemIDplus-4] Entry on furosemide in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[5] Brunelli C, Bicchi C, Di Stilo A, Salomone A, Vincenti M: High-speed gas chromatography in doping control: fast-GC and fast-GC / MS determination of beta-adrenoceptor ligands and diuretics. , J Sep Sci. 2006 Dec; 29 (18): 2765-71, PMID 17305237

[6] Sora DI, Udrescu S, Albu F, David V, Medvedovici A: Analytical issues in HPLC / MS / MS simultaneous assay of furosemide, spironolactone and canrenone in human plasma samples. , J Pharm Biomed Anal. 2010 Sep 5; 52 (5): 734-40, PMID 20307949

[7] WADA : Doping List 2016 (PDF).