Xipamide

Xipamide
Names
IUPAC name
  • 4-chloro-N-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide
Clinical data
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • contraindication
Routes of
use		By mouth
External links
AHFS/Drugs.comInternational Drug Names
Legal
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetics
Bioavailability95%
Protein binding98%
Metabolismglucuronide (30%)
Elimination half-life5.8 to 8.2 hours
Excretionkidney (1/3) and bile duct (2/3)
Identifiers
CAS Number
  • 14293-44-8 checkY
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
ATC code
Chemical and physical data
FormulaC15H15ClN2O4S
Molar mass354.81 g·mol−1
3D model (JSmol)
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

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.[1]

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).[2]

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 kidney failure renders xipamide ineffective.[3]

Uses

Xipamide is used for[2][3]

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.[3]

Dosage

Initially 40 mg, it can be reduced to 10–20 mg to prevent a relapse.[3]

The lowest effective dose is 5 mg. More than 60 mg have no additional effects.[2]

Adverse effects

Contraindications

Interactions

  • Xipamide lowers the renal clearance of lithium which can lead to lithium intoxication.[2] (This interaction is classified as medium.[4])

Combinations requiring special precautions

The product information requests special precautions for these combinations:[2]

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.[5]

References

  1. ↑ "2.9. Cardiovascular system: oedema". BNF 86: September 2023 - March 2024. BMJ Group and the Pharmaceutical Press. 2023. p. 254. ISBN 978-0857114617.
  2. 1 2 3 4 5 6 7 Jasek W, ed. (2007). Austria-Codex (in Deutsch). Vol. 1 (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. pp. 600–603. ISBN 978-3-85200-181-4.
  3. 1 2 3 4 5 Dinnendahl V, Fricke U, eds. (2007). Arzneistoff-Profile (in Deutsch). Vol. 10 (21 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.
  4. 1 2 3 4 5 Klopp T, ed. (2007). Arzneimittel-Interaktionen (in Deutsch) (2007/2008 ed.). Arbeitsgemeinschaft für Pharmazeutische Information. ISBN 978-3-85200-184-5.
  5. ↑ Williams R (17 July 2012). "Frank Schleck tests positive for banned diuretic and is out of Tour". The Guardian. London. Archived from the original on 2013-11-11. Retrieved 2012-07-18.
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