Xipamide

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Xipamide
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy; category	contraindication;
Routes of; administration	oral
ATC code	C03BA10 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	95%
Protein binding	98%
Metabolism	glucuronide (30%)
Elimination half-life	5.8 to 8.2 hours
Excretion	renal (1/3) and biliary (2/3)
Identifiers
	IUPAC name 4-chloro-N-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide;
CAS Number	14293-44-8 ;
PubChem CID	26618;
ChemSpider	24795 ;
UNII	4S9EY0NUEC;
KEGG	D06341 ;
ChEMBL	ChEMBL517199 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C15H15ClN2O4S
Molar mass	354.80 g/mol
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C(=CC=C1)C)NC(=O)C2=CC(=C(C=C2O)Cl)S(=O)(=O)N;
	InChI InChI=1S/C15H15ClN2O4S/c1-8-4-3-5-9(2)14(8)18-15(20)10-6-13(23(17,21)22)11(16)7-12(10)19/h3-7,19H,1-2H3,(H,18,20)(H2,17,21,22) ; Key:MTZBBNMLMNBNJL-UHFFFAOYSA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Xipamide is a sulfonamide diuretic drug marketed by Eli Lilly under the trade names Aquaphor (in Germany) and Aquaphoril (in Austria). It is used for the treatment of oedema and hypertension.

Mechanism of Action

Like the structurally related thiazide diuretics, xipamide acts on the kidneys to reduce sodium reabsorption in the distal convoluted tubule. This increases the osmolarity in the lumen, causing less water to be reabsorbed by the collecting ducts. This leads to increased urinary output. Unlike the thiazides, xipamide reaches its target from the peritubular side (blood side).^[1]

Additionally, it increases the secretion of potassium in the distal tubule and collecting ducts. In high doses it also inhibits the enzyme carbonic anhydrase which leads to increased secretion of bicarbonate and alkalizes the urine.

Unlike with thiazides, only terminal renal failure renders xipamide ineffective.^[2]

Uses

Xipamide is used for^[1]^[2]

cardiac oedema caused by decompensation of heart failure
renal oedema, chronic renal disease (but not with anuria)
hepatic oedema caused by cirrhosis
ascites
lymphoedema
hypertension in combination with chronic renal disease

Pharmacokinetics

After oral administration, 20 mg of xipamide are resorbed quickly and reach the peak plasma concentration of 3 mg/l within an hour. The diuretic effect starts about an hour after administration, reaches its peak between the third and sixth hour, and lasts for nearly 24 hours.

One third of the dose is glucuronidized, the rest is excreted directly through the kidney (1/3) and the faeces (2/3). The total plasma clearance is 30-40 ml/min. Xipamide can be filtrated by haemodialysis but not by peritoneal dialysis.^[2]

Dosage

Initially 40 mg, it can be reduced to 10–20 mg to prevent a relapse.^[2]

The lowest effective dose is 5 mg. More than 60 mg have no additional effects.^[1]

Adverse Effects

more than 1/10 of all patients^[1]
- hypokalaemia, which can lead to nausea, muscular weakness or cramps, and ECG abnormities
1/100 to 1/10
- hyponatraemia, which can lead to headache, nausea, drowsiness or confusion
- orthostatic hypotension
- initially increase of urea, uric acid and creatinine, which can lead to a gout attack in predisposed patients
1/1000 to 1/10,000
- allergic reactions of the skin
- hyperlipidaemia
less than 1/10,000
- haemorrhagic pancreatitis
- acute interstitial nephritis
- thrombocytopenia, leucopenia

Contraindications

anuria
praecoma and coma hepaticum
hypovolemia, hyponatremia, hypokalemia
hypercalcemia
gout
sulfonamide hypersensitivity
pregnancy, lactation period^[1]^[2]

Interactions

Not recommended combinations

Xipamide lowers the renal clearance of lithium which can lead to lithium intoxication.^[1] (This interaction is classified as medium.^[3])

Combinations requiring special precautions

The product information requests special precautions for these combinations:^[1]

The antihypertensive effect can be increased by ACE inhibitors, barbiturates, phenothiazines, tricyclic antidepressants, alcohol, etc. (Classified as minor.^[3])

NSAIDs can reduce the antihypertensive and diuretic effects. Xipamide increases the neurotoxicity of high doses of salicylates. (Classified as minor.^[3])

Toxicity of cardiac glycosides is increased due to hypokalemia and hypomagnesemia.(Classified as minor.^[3])

Antiarrhythmic agents (classes Ia and III), phenothiazines and other antipsychotics increase the risk of torsade de pointes due to hypokalemia.

Interactions not included in the product information

Xipamide can reduce the effect of antidiabetics. (Classified as minor.^[3])

Banned use in sport

On 17 July 2012, cyclist Fränk Schleck was removed from the Tour de France by his team RadioShack-Nissan after his A-sample returned traces of xipamide.^[4]

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 ^1.6 Jasek, W, ed. (2007). Austria-Codex (in German). 1 (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. pp. 600–603. ISBN 978-3-85200-181-4.
↑ ^2.0 ^2.1 ^2.2 ^2.3 ^2.4 Dinnendahl, V, Fricke, U, ed. (2007). Arzneistoff-Profile (in German). 10 (21 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.
↑ ^3.0 ^3.1 ^3.2 ^3.3 ^3.4 Klopp, T, ed. (2007). Arzneimittel-Interaktionen (in German) (2007/2008 ed.). Arbeitsgemeinschaft für Pharmazeutische Information. ISBN 978-3-85200-184-5.
↑ Richard Williams in Pau (17 July 2012). "Frank Schleck tests positive for banned diuretic and is out of Tour". London: The Guardian. Retrieved 2012-07-18.

[Austria-Codex-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 ^1.6 Jasek, W, ed. (2007). Austria-Codex (in German). 1 (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. pp. 600–603. ISBN 978-3-85200-181-4.

[Arzneistoff-Profile-2] 2.0 ^2.1 ^2.2 ^2.3 ^2.4 Dinnendahl, V, Fricke, U, ed. (2007). Arzneistoff-Profile (in German). 10 (21 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.

[Arzneimittel-Interaktionen-3] 3.0 ^3.1 ^3.2 ^3.3 ^3.4 Klopp, T, ed. (2007). Arzneimittel-Interaktionen (in German) (2007/2008 ed.). Arbeitsgemeinschaft für Pharmazeutische Information. ISBN 978-3-85200-184-5.

[4] Richard Williams in Pau (17 July 2012). "Frank Schleck tests positive for banned diuretic and is out of Tour". London: The Guardian. Retrieved 2012-07-18.

[1]

[2]

[3]

[4]

Clinical data


AHFS/Drugs.com	International Drug Names
Pregnancy category	contraindication
Routes of administration	oral
ATC code	C03BA10 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	95%
Protein binding	98%
Metabolism	glucuronide (30%)
Elimination half-life	5.8 to 8.2 hours
Excretion	renal (1/3) and biliary (2/3)
Identifiers
IUPAC name 4-chloro-N-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide
CAS Number	14293-44-8^Y
PubChem CID	26618
ChemSpider	24795^N
UNII	4S9EY0NUEC
KEGG	D06341^Y
ChEMBL	ChEMBL517199^N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₁₅H₁₅ClN₂O₄S
Molar mass	354.80 g/mol
3D model (JSmol)	Interactive image
SMILES CC1=C(C(=CC=C1)C)NC(=O)C2=CC(=C(C=C2O)Cl)S(=O)(=O)N
InChI InChI=1S/C15H15ClN2O4S/c1-8-4-3-5-9(2)14(8)18-15(20)10-6-13(23(17,21)22)11(16)7-12(10)19/h3-7,19H,1-2H3,(H,18,20)(H2,17,21,22)^N Key:MTZBBNMLMNBNJL-UHFFFAOYSA-N^N
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