Butizide

Butizide
Clinical data
Other names	thiabutazide, buthiazide
ATC code	C03EA14 (WHO) (combination with potassium-sparing diuretics);
Pharmacokinetic data
Bioavailability	85%
Protein binding	60–80%
Metabolism	hepatic
Elimination half-life	4 hours
Excretion	30% unchanged with the urine
Identifiers
CAS Number	2043-38-1;
PubChem CID	16274;
ChemSpider	15442 ;
UNII	W00SSD35VW;
KEGG	D03189;
CompTox Dashboard (EPA)	DTXSID6022713 ;
ECHA InfoCard	100.016.409
Chemical and physical data
Formula	C11H16ClN3O4S2
Molar mass	353.84 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)CC1NC2=CC(=C(C=C2S(=O)(=O)N1)S(=O)(=O)N)Cl;
	InChI InChI=1S/C11H16ClN3O4S2/c1-6(2)3-11-14-8-4-7(12)9(20(13,16)17)5-10(8)21(18,19)15-11/h4-6,11,14-15H,3H2,1-2H3,(H2,13,16,17) ; Key:HGBFRHCDYZJRAO-UHFFFAOYSA-N ;

Butizide (or thiabutazide) is a diuretic of the thiazide class.[1]

Medical uses

Butizide is used in combination with the potassium-sparing diuretic spironolactone for the second-line treatment of edema caused by heart failure, and for difficult cases of hypertension.[1]

Adverse effects

Interactions

The hypotensive effects of butizide can be increased by antihypertensive drugs (especially ACE inhibitors), barbiturates, tricyclic antidepressants, and ethanol. Combinatino with beta blockers can increase blood glucose levels; and conversely, butizide can decrease the effects of antidiabetic drugs. As butizide lowers blood potassium and magnesium levels, it can increase the effects of cardiac glycosides. It can also increase lithium toxicity.[1]

Nonsteroidal anti-inflammatory drugs can decrease the diuretic effect of butizide.[1]

Pharmacology

Mechanism of action

Pharmacokinetics

Butizide is quickly absorbed from the gut with a bioavailability of 85%. It reaches highest blood plasma concentrations after 2.5 hours. Plasma protein binding is 60 to 80%. While the substance is metabolised in the liver, 30% are excreted in unchanged from with the urine. Elimination half-life is about four hours.[1]

Chemistry

Synthesis

Thiabutazide synthesis[2]

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References

Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. 2018. Aldactone-Saltucin Forte-Hartkapseln.
Topliss, J. G.; Sherlock, M. H.; Clarke, F. H.; Daly, M. C.; Pettersen, B. W.; Lipski, J.; Sperber, N. (1961). "3-Substituted Dihydrobenzothiadiazine 1,1-Dioxides as Diuretic Agents". The Journal of Organic Chemistry. 26 (10): 3842. doi:10.1021/jo01068a053.

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[AustriaCodex-1] Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. 2018. Aldactone-Saltucin Forte-Hartkapseln.

[2] Topliss, J. G.; Sherlock, M. H.; Clarke, F. H.; Daly, M. C.; Pettersen, B. W.; Lipski, J.; Sperber, N. (1961). "3-Substituted Dihydrobenzothiadiazine 1,1-Dioxides as Diuretic Agents". The Journal of Organic Chemistry. 26 (10): 3842. doi:10.1021/jo01068a053.