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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:42 UTC
HMDB IDHMDB0014456
Secondary Accession Numbers
  • HMDB14456
Metabolite Identification
Common NameEthoxzolamide
DescriptionEthoxzolamide is only found in individuals that have used or taken this drug. It is a carbonic anhydrase inhibitor used as diuretic and in glaucoma. It may cause hypokalemia. [PubChem]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.
Structure
Data?1582753182
Synonyms
ValueSource
6-Ethoxy-2-benzothiazolesulfonamideChEBI
6-Ethoxy-benzothiazole-2-sulfonic acid amideChEBI
6-Ethoxybenzothiazole-2-sulfonamideChEBI
EthoxazolamideChEBI
EthoxyzolamideChEBI
CardraseKegg
6-Ethoxy-2-benzothiazolesulphonamideGenerator
6-Ethoxy-benzothiazole-2-sulfonate amideGenerator
6-Ethoxy-benzothiazole-2-sulphonate amideGenerator
6-Ethoxy-benzothiazole-2-sulphonic acid amideGenerator
6-Ethoxybenzothiazole-2-sulphonamideGenerator
6-Ethoxy-1,3-benzothiazole-2-sulfonamideHMDB
EtoxzolamideHMDB
EthamideHMDB
Chemical FormulaC9H10N2O3S2
Average Molecular Weight258.317
Monoisotopic Molecular Weight258.013283576
IUPAC Name6-ethoxy-1,3-benzothiazole-2-sulfonamide
Traditional Nameethoxzolamide
CAS Registry Number452-35-7
SMILES
CCOC1=CC2=C(C=C1)N=C(S2)S(N)(=O)=O
InChI Identifier
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)
InChI KeyOUZWUKMCLIBBOG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazoles
Sub ClassNot Available
Direct ParentBenzothiazoles
Alternative Parents
Substituents
  • 1,3-benzothiazole
  • Alkyl aryl ether
  • Organosulfonic acid amide
  • Benzenoid
  • Azole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Thiazole
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Ether
  • Azacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point189 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.69 g/LNot Available
LogP0.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available152.69http://allccs.zhulab.cn/database/detail?ID=AllCCS00001020
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.69 g/LALOGPS
logP10(1.87) g/LALOGPS
logP10(1.6) g/LChemAxon
logS10(-2.6) g/LALOGPS
pKa (Strongest Acidic)7.51ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.28 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.97 m³·mol⁻¹ChemAxon
Polarizability25.27 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.27431661259
DarkChem[M-H]-154.03631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EthoxzolamideCCOC1=CC2=C(C=C1)N=C(S2)S(N)(=O)=O3440.8Standard polar33892256
EthoxzolamideCCOC1=CC2=C(C=C1)N=C(S2)S(N)(=O)=O2602.9Standard non polar33892256
EthoxzolamideCCOC1=CC2=C(C=C1)N=C(S2)S(N)(=O)=O2457.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethoxzolamide,1TMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N[Si](C)(C)C)SC2=C12399.1Semi standard non polar33892256
Ethoxzolamide,1TMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N[Si](C)(C)C)SC2=C12356.4Standard non polar33892256
Ethoxzolamide,1TMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N[Si](C)(C)C)SC2=C13370.4Standard polar33892256
Ethoxzolamide,2TMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)SC2=C12396.1Semi standard non polar33892256
Ethoxzolamide,2TMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)SC2=C12528.9Standard non polar33892256
Ethoxzolamide,2TMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)SC2=C13195.5Standard polar33892256
Ethoxzolamide,1TBDMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)SC2=C12652.9Semi standard non polar33892256
Ethoxzolamide,1TBDMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)SC2=C12606.7Standard non polar33892256
Ethoxzolamide,1TBDMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)SC2=C13393.1Standard polar33892256
Ethoxzolamide,2TBDMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)SC2=C12867.6Semi standard non polar33892256
Ethoxzolamide,2TBDMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)SC2=C12997.2Standard non polar33892256
Ethoxzolamide,2TBDMS,isomer #1CCOC1=CC=C2N=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)SC2=C13246.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ethoxzolamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-1980000000-ec067e5e789b4033729a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethoxzolamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethoxzolamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxzolamide LC-ESI-qTof , Positive-QTOFsplash10-0uk9-3900000000-26213ae94b481c8760072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxzolamide , positive-QTOFsplash10-0uk9-3900000000-26213ae94b481c8760072017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 10V, Positive-QTOFsplash10-0zfr-0960000000-30176db233c762327bb82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 20V, Positive-QTOFsplash10-0fb9-0920000000-12f2a2d76e8d1872359c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 40V, Positive-QTOFsplash10-067i-6900000000-150c9526ca35c54438182016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 10V, Negative-QTOFsplash10-004i-4930000000-03953ab2f5340a6bde832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 20V, Negative-QTOFsplash10-004i-5900000000-829e196c0d5d75dd73ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 40V, Negative-QTOFsplash10-0ufr-3910000000-a39e42db3eb1f695354e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 10V, Positive-QTOFsplash10-0a4i-0090000000-8af0d07ca07343f13e172021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 20V, Positive-QTOFsplash10-0a4i-0090000000-a6c40b0c6fafeaf3e12b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 40V, Positive-QTOFsplash10-0fvi-1930000000-f047c1738e723ac089f72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 10V, Negative-QTOFsplash10-004i-9150000000-98acc35e866c26644fd52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 20V, Negative-QTOFsplash10-004i-9030000000-bb0adaec97d4ce4f9bd82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxzolamide 40V, Negative-QTOFsplash10-004i-9210000000-2862fcb806ab3f11f4202021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00311 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00311 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00311
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3179
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthoxzolamide
METLIN IDNot Available
PubChem Compound3295
PDB IDNot Available
ChEBI ID101096
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular weight:
28870.0
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:10995826 ]
  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:12956733 ]
  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:7929150 ]
  4. Siffert W, Gros G: Carbonic anhydrase C in white-skeletal-muscle tissue. Biochem J. 1982 Sep 1;205(3):559-66. [PubMed:6816217 ]
  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:10649985 ]
  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. doi: 10.1016/j.bmc.2009.05.063. Epub 2009 May 30. [PubMed:19520577 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular weight:
29245.895
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:18336310 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:
CA4
Uniprot ID:
P22748
Molecular weight:
35032.075
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:18336310 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide.
Gene Name:
CA7
Uniprot ID:
P43166
Molecular weight:
23451.435
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:18336310 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
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:10991988 ]