xipamide   Click here for help

GtoPdb Ligand ID: 7900

Synonyms: BE-1293 | Diurexan® | MJF-10938
Approved drug
xipamide is an approved drug (UK (2002))
Compound class: Synthetic organic
Comment: Xipamide is a sulfonamide diuretic.

xipamide is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 117.87
Molecular weight 354.04
XLogP 2.55
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O=C(c1cc(c(cc1O)Cl)S(=O)(=O)N)Nc1c(C)cccc1C
Isomeric SMILES O=C(c1cc(c(cc1O)Cl)S(=O)(=O)N)Nc1c(C)cccc1C
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)
InChI Key MTZBBNMLMNBNJL-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Xipamide is used for the treatment of oedema and hypertension.
This drug is not approved by the US FDA or EMA. It has been used in the UK since 2002, and is available in other countries under various trade names. Click here to link to Drugs.com's list of internationally marketed xipamide drugs.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Xipamide acts on the kidneys in a similar manner to the thiazide diuretics, acting to reduce sodium reabsorption in the distal convoluted tubule. These drugs block the active reabsorption of chloride in the ascending loop of Henle by inhibiting the thiazide-sensitive sodium-chloride symporter, NCC (SLC12A3). This results in excretion of sodium, chloride and water, thus reducing fluid retention and oedema. At high concentrations xipamide can also inhibit carbonic anhydrases [1].
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)