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targets (4) transporters (1)
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Identification
Name Ethoxzolamide
Accession Number DB00311 (APRD00732, DB07727)
Type small molecule
Groups approved
Description

A carbonic anhydrase inhibitor used as diuretic and in glaucoma. It may cause hypokalemia. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
6-Ethoxy-1,3-benzothiazole-2-sulfonamide
Ethoxazolamide
Ethoxyzolamide
Etoxzolamide
Salts Not Available
Brand names
Name Company
Cardrase
Diuretic C
Ethamide
Glaucotensil
Redupresin
Brand mixtures Not Available
Categories
  • Diuretics
  • Carbonic Anhydrase Inhibitors
CAS number 452-35-7
Weight Average: 258.317
Monoisotopic: 258.013283576
Chemical Formula C9H10N2O3S2
InChI Key InChIKey=OUZWUKMCLIBBOG-UHFFFAOYSA-N
InChI
InChI=1S/C9H10N2O3S2/c1-2-14-6-3-4-7-8(5-6)15-9(11-7)16(10,12)13/h3-5H,2H2,1H3,(H2,10,12,13)
Plain Text
IUPAC Name
6-ethoxy-1,3-benzothiazole-2-sulfonamide
SMILES
CCOC1=CC2=C(C=C1)N=C(S2)S(N)(=O)=O
Plain Text
Mass Spec show (10.1 KB)
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Ethers
  • Anisoles
  • Benzothiazoles
Substructures
  • Phenols and Derivatives
  • Sulfonyls
  • Ethers
  • Benzene and Derivatives
  • Thiazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Sulfonamides
  • Benzothiazoles
  • Phenyl Esters
Pharmacology
Indication For use in the treatment of duodenal ulcers, as a diuretic, and in the treatment of glaucoma, and may also be useful in the treatment of seizures associated with epilepsy.
Pharmacodynamics Ethoxzolamide, a sulfonamide, inhibits carbonic anhydrase activity in proximal renal tubules to decrease reabsorption of water, sodium, potassium, bicarbonate. It also decreases carbonic anhydrase in the CNS, increasing the seizure threshold. This reduction in carbonic anhydrase also reduces the intraocular pressure in the eye by decreasing aqueous humor.
Mechanism of action Ethoxzolamide binds and inhibits carbonic anhydrase I. Carbonic anhydrase plays an essential role in facilitating the transport of carbon dioxide and protons in the intracellular space, across biological membranes and in the layers of the extracellular space. The inhibition of this enzyme effects the balance of applicable membrane equilibrium systems. This reduction in carbonic anhydrase also reduces the intraocular pressure in the eye by decreasing aqueous humor.
Absorption Rapidly absorbed with 65% bioavailability
Volume of distribution Not Available
Protein binding ~89%
Metabolism Not Available
Route of elimination Not Available
Half life 2.5-5.5 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
  • Allergan pharmaceutical
Packagers Not Available
Dosage forms
Form Route Strength
Capsule Oral
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 189 °C PhysProp
water solubility 40 mg/L YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 2.01 HANSCH,C ET AL. (1995)
logS -3.81 ADME Research, USCD
Predicted Properties
Property Value Source
water solubility 6.88e-01 g/l ALOGPS
logP 1.87 ALOGPS
logP 1.6 ChemAxon
logS -2.6 ALOGPS
pKa (strongest acidic) 7.51 ChemAxon
pKa (strongest basic) -1.9 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 82.28 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 59.97 ChemAxon
polarizability 25.27 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D02441 Link_out
PubChem Compound 3295 Link_out
PubChem Substance 46509023 Link_out
ChemSpider 3179 Link_out
BindingDB 10882 Link_out
ChEBI 101096 Link_out
ChEMBL 101096 Link_out
Therapeutic Targets Database DAP000598 Link_out
PharmGKB PA164754743 Link_out
HET EZL Link_out
Wikipedia http://en.wikipedia.org/wiki/Ethoxzolamide Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Carbonic anhydrase 1

Pharmacological action: yes
Actions: inhibitor

Reversible hydration of carbon dioxide

Organism class: human
UniProt ID: P00915 Link_out
Gene: CA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kohling R, Vreugdenhil M, Bracci E, Jefferys JG: Ictal epileptiform activity is facilitated by hippocampal GABAA receptor-mediated oscillations. J Neurosci. 2000 Sep 15;20(18):6820-9. Pubmed
  2. Perez Velazquez JL: Bicarbonate-dependent depolarizing potentials in pyramidal cells and interneurons during epileptiform activity. Eur J Neurosci. 2003 Sep;18(5):1337-42. Pubmed
  3. Heck RW, Tanhauser SM, Manda R, Tu C, Laipis PJ, Silverman DN: Catalytic properties of mouse carbonic anhydrase V. J Biol Chem. 1994 Oct 7;269(40):24742-6. Pubmed
  4. Siffert W, Gros G: Carbonic anhydrase C in white-skeletal-muscle tissue. Biochem J. 1982 Sep 1;205(3):559-66. Pubmed
  5. Scozzafava A, Briganti F, Ilies MA, Supuran CT: Carbonic anhydrase inhibitors: synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes. J Med Chem. 2000 Jan 27;43(2):292-300. Pubmed
  6. Bertucci A, Innocenti A, Zoccola D, Scozzafava A, Tambutte S, Supuran CT: Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorg Med Chem. 2009 Jul 15;17(14):5054-8. Epub 2009 May 30. Pubmed

2. Carbonic anhydrase 2

Pharmacological action: yes
Actions: inhibitor

Reversible hydration of carbon dioxide

Organism class: human
UniProt ID: P00918 Link_out
Gene: CA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. Pubmed

3. Carbonic anhydrase 4

Pharmacological action: yes
Actions: inhibitor

Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4

Organism class: human
UniProt ID: P22748 Link_out
Gene: CA4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. Pubmed

4. Carbonic anhydrase 7

Pharmacological action: yes
Actions: inhibitor

Reversible hydration of carbon dioxide

Organism class: human
UniProt ID: P43166 Link_out
Gene: CA7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. Pubmed
Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Uwai Y, Saito H, Hashimoto Y, Inui KI: Interaction and transport of thiazide diuretics, loop diuretics, and acetazolamide via rat renal organic anion transporter rOAT1. J Pharmacol Exp Ther. 2000 Oct;295(1):261-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19