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'''Xipamide''' is a [[diuretic]]. It is typically used to lower blood pressure by means of drawing sodium and potassium from the blood.  This causes water to be drawn from the blood into the kidneys where it is excreted in [[urine]].  This has the overall affect of decreasing the volume of fluid circulating through the blood vessels thereby decreasing blood pressure. <ref>[http://www.tiscali.co.uk/lifestyle/healthfitness/health_advice/netdoctor/archive/100003248.html Xipamide<!-- Bot generated title -->]</ref>
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 448072116
| IUPAC_name = 4-chloro-''N''-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide
| image = Xipamide.png
| image2 = Xipamide balls.png


==References==
<!--Clinical data-->
| tradename =
| Drugs.com = {{drugs.com|international|xipamide}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = contraindication
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = Rx
| routes_of_administration = oral


<!--Pharmacokinetic data-->
| bioavailability = 95%
| protein_bound = 98%
| metabolism = [[glucuronide]] (30%)
| elimination_half-life = 5.8 to 8.2 hours
| excretion = [[renal]] (1/3) and biliary (2/3)


<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 14293-44-8
| ATC_prefix = C03
| ATC_suffix = BA10
| ATC_supplemental = 
| PubChem = 26618
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4S9EY0NUEC
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D06341
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 517199
|  ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 24795
|  InChI = 1/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)
|  InChIKey = MTZBBNMLMNBNJL-UHFFFAOYAO
|  StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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)
|  StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = MTZBBNMLMNBNJL-UHFFFAOYSA-N
<!--Chemical data-->
| chemical_formula = 
| C=15 | H=15 | Cl=1 | N=2 | O=4 | S=1
| molecular_weight = 354.80 g/mol
| smiles = CC1=C(C(=CC=C1)C)NC(=O)C2=CC(=C(C=C2O)Cl)S(=O)(=O)N
}}
'''Xipamide''' is a sulfonamide [[diuretic]] drug marketed by [[Eli Lilly and Company|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 diuretic]]s, xipamide acts on the kidneys to reduce [[sodium]] reabsorption in the [[distal convoluted tubule]]. This increases the [[osmolarity]] in the [[Lumen (anatomy)|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).<ref name="Austria-Codex" />
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.<ref name="Arzneistoff-Profile">{{cite book|title=Arzneistoff-Profile|editor=Dinnendahl, V, Fricke, U|publisher=Govi Pharmazeutischer Verlag|location=Eschborn, Germany|year=2007|edition=21|volume=10|isbn=978-3-7741-9846-3|language=German}}</ref>
== Uses ==
Xipamide is used for<ref name="Austria-Codex" /><ref name="Arzneistoff-Profile" />
*[[cardiac]] oedema caused by [[Heart Failure#Acute decompensation|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&nbsp;mg of xipamide are resorbed quickly and reach the peak plasma concentration of 3&nbsp;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 [[glucuronidation|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]].<ref name="Arzneistoff-Profile" />
== Dosage ==
Initially 40&nbsp;mg, it can be reduced to 10–20&nbsp;mg to prevent a relapse.<ref name="Arzneistoff-Profile" />
The lowest effective dose is 5&nbsp;mg. More than 60&nbsp;mg have no additional effects.<ref name="Austria-Codex" />
== Adverse effects ==
*'''more than 1/10 of all patients'''<ref name="Austria-Codex" />
**[[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 (medicine)|sulfonamide]] hypersensitivity
*pregnancy, lactation period<ref name="Austria-Codex" /><ref name="Arzneistoff-Profile" />
== Interactions ==
===Not recommended combinations===
*Xipamide lowers the renal clearance of [[lithium pharmacology|lithium]] which can lead to lithium intoxication.<ref name="Austria-Codex">{{cite book|title=Austria-Codex|editor=Jasek, W|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2007|edition=2007/2008|volume=1|pages=600–603|isbn=978-3-85200-181-4|language=German}}</ref> (This interaction is classified as ''medium''.<ref name="Arzneimittel-Interaktionen">{{cite book|title=Arzneimittel-Interaktionen|editor=Klopp, T|publisher=Arbeitsgemeinschaft für Pharmazeutische Information|year=2007|edition=2007/2008|isbn=978-3-85200-184-5|language=German}}</ref>)
===Combinations requiring special precautions===
The product information requests special precautions for these combinations:<ref name="Austria-Codex" />
*The antihypertensive effect can be increased by [[ACE inhibitor]]s, [[barbiturate]]s, [[phenothiazine]]s, [[tricyclic antidepressant]]s, [[alcohol]], etc. (Classified as ''minor''.<ref name="Arzneimittel-Interaktionen" />)
*[[NSAID]]s can reduce the antihypertensive and diuretic effects. Xipamide increases the neurotoxicity of high doses of salicylates. (Classified as ''minor''.<ref name="Arzneimittel-Interaktionen" />)
*Toxicity of [[cardiac glycoside]]s is increased due to hypokalemia and [[hypomagnesemia]].(Classified as ''minor''.<ref name="Arzneimittel-Interaktionen" />)
*[[Antiarrhythmic agent]]s (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''.<ref name="Arzneimittel-Interaktionen" />)
== 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.<ref>{{cite news|author=Richard Williams in Pau |url=http://www.guardian.co.uk/sport/2012/jul/17/tour-de-france-frank-schleck |title=Frank Schleck tests positive for banned diuretic and is out of Tour |publisher=The Guardian |date= 17 July 2012|accessdate=2012-07-18 |location=London}}</ref>
== References ==
{{Reflist}}
{{Reflist}}
 
{{Diuretics}}
[[Category:Diuretics]]
[[Category:Diuretics]]
 
[[Category:Eli Lilly and Company]]
[[it:Xipamide]]
[[Category:Organochlorides]]
[[pt:Xipamida]]
[[Category:Salicylanilides]]
{{WikiDoc Sources}}
[[Category:Sulfonamides]]

Revision as of 01:19, 25 July 2014

Xipamide
Clinical data
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • contraindication
Routes of
administration		oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability95%
Protein binding98%
Metabolismglucuronide (30%)
Elimination half-life5.8 to 8.2 hours
Excretionrenal (1/3) and biliary (2/3)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
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
FormulaC15H15ClN2O4S
Molar mass354.80 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

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]

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

Contraindications

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]

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

Interactions not included in the product information

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. ↑ 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. ↑ 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. ↑ 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.

Template:Diuretics

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