Xipamide

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Xipamide
File:Xipamide.svg
File:Xipamide balls.png
Systematic (IUPAC) name
4-chloro-N-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy
category
  • contraindication
Legal status
  • ℞ (Prescription only)
Routes of
administration
oral
Pharmacokinetic data
Bioavailability 95%
Protein binding 98%
Metabolism glucuronide (30%)
Biological half-life 5.8 to 8.2 hours
Excretion renal (1/3) and biliary (2/3)
Identifiers
CAS Number 14293-44-8 YesY
ATC code C03BA10 (WHO)
PubChem CID: 26618
IUPHAR/BPS 7900
ChemSpider 24795 N
UNII 4S9EY0NUEC YesY
KEGG D06341 YesY
ChEMBL CHEMBL517199 N
Chemical data
Formula C15H15ClN2O4S
Molecular mass 354.80 g/mol
  • CC1=C(C(=CC=C1)C)NC(=O)C2=CC(=C(C=C2O)Cl)S(=O)(=O)N
  • 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
 NYesY (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]

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

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