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Compound Detail

CHEMBL18

ETHOXZOLAMIDE
💊 Approved Drug
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💊 Approved Drug
CCOc1ccc2nc(S(N)(=O)=O)sc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL18
Name ETHOXZOLAMIDE
Phase Approved
Structure Type MOL
InChI Key OUZWUKMCLIBBOG-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Cardrase Ethamide Ethoxzolamide NSC-10679
34
Targets
465
Activities
3
Assay Types
0
PK Parameters
20
Publications
4
Known Names
1
Mechanisms

Molecular Properties

258.3
MW (Da)
1.34
ALogP
5
HBA
1
HBD
82.3
PSA (Ų)
0.90
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -zolamide

Extended Properties

Molecular Formula C9H10N2O3S2
MW 258.32
Aromatic Rings 2
Heavy Atoms 16
NP-Likeness -2.07

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Carbonic anhydrase inhibitor INHIBITOR Carbonic anhydrase ✓ ✓

Activity Summary

Ki 444 meas. best 9.31
Kd 11 meas. best 9.15
IC50 10 meas. best 9.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 9
CHEMBL3594
 IC50 9.6 9.3 0.2 2
Carbonic anhydrase 2
CHEMBL205
 IC50 9.52 8.856 0.3 5
Carbonic anhydrase 2
CHEMBL205
 Ki 9.31 8.0272 0.5 107
Unchecked
CHEMBL612545
 Ki 9.16 6.7284 0.7 55
Carbonic anhydrase 2
CHEMBL205
 Kd 9.15 9.055 0.7 2
Carbonic anhydrase 7
CHEMBL2326
 Kd 9.15 9.15 0.7 2
Carbonic anhydrase 7
CHEMBL2326
 Ki 9.11 9.1009 0.8 11
Carbonic anhydrase V
CHEMBL2111457
 Ki 8.7 8.7 2.0 1
Carbonic anhydrase 14
CHEMBL3510
 Ki 8.6 7.85 2.5 12
Carbonic anhydrase, alpha family
CHEMBL3621035
 Ki 8.39 8.39 4.1 1
Carbonic anhydrase 1
CHEMBL261
 IC50 8.1 7.69 8.0 3
Carbonate dehydratase
CHEMBL3745586
 Ki 8.03 8.03 9.3 1
Carbonic anhydrase 13
CHEMBL3912
 Kd 7.89 7.89 13.0 2
Carbonic anhydrase 4
CHEMBL281
 Ki 7.89 7.89 13.0 11
Carbonic anhydrase 1
CHEMBL261
 Kd 7.85 7.85 14.0 2
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Ki 7.72 7.72 19.0 8
Carbonic anhydrase 12
CHEMBL3242
 Ki 7.66 7.6448 22.0 27
Carbonic anhydrase 1
CHEMBL261
 Ki 7.6 7.5379 25.0 97
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 7.6 7.6 25.0 8
Carbonic anhydrase 2
CHEMBL6068
 Ki 7.57 7.57 27.0 1
Carbonic anhydrase 6
CHEMBL3025
 Kd 7.48 7.48 33.0 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 7.47 7.4004 34.0 52
Carbonic anhydrase 12
CHEMBL3242
 Kd 7.44 7.44 36.0 2
Alpha carbonic anhydrase
CHEMBL1075028
 Ki 7.41 7.41 39.4 2
Carbonic anhydrase 6
CHEMBL3025
 Ki 7.37 7.056 43.0 10
Carbonic anhydrase 13
CHEMBL2186
 Ki 7.3 7.3 50.0 4
Carbonic anhydrase 15
CHEMBL5973
 Ki 7.24 7.24 58.0 2
Delta carbonic anhydrase
CHEMBL3097982
 Ki 7.07 7.07 85.1 1
Carbonic anhydrase 2
CHEMBL1697676
 Ki 7.06 7.06 87.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 7.03 6.8189 93.0 9
Carbonic anhydrase
CHEMBL5931
 Ki 7.01 5.905 98.4 2
Carbonic anhydrase
CHEMBL1649055
 Ki 6.98 6.98 105.0 1
Carbonic anhydrase
CHEMBL4211
 Ki 6.81 6.76 155.0 2
AGAP002992-PA
CHEMBL3399914
 Ki 6.73 6.73 185.0 1
Carbonic anhydrase
CHEMBL3932
 Ki 6.7 6.415 200.0 2
Astrosclerin-3
CHEMBL1944499
 Ki 6.41 6.41 387.0 1
Beta-carbonic anhydrase 1
CHEMBL5631
 Ki 5.99 5.99 1030.0 1
Carbonic anhydrase
CHEMBL5337
 Ki 5.97 5.97 1070.0 4
Carbonic anhydrase
CHEMBL6185
 Ki 5.5 5.5 3125.0 1
Carbonic anhydrase 3
CHEMBL2885
 Ki 5.3 5.3 5000.0 1
Carbonic anhydrase
CHEMBL3926
 Ki 5.27 5.27 5350.0 1
Carbonic anhydrase 3
CHEMBL1944498
 Ki 5.03 5.03 9443.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 9 IC50 = 0.25 nM 9.6 Inhibition of human carbonic anhydrase-9 incubated for 15 mins prior to testing ... 30746068
Carbonic anhydrase 2 IC50 = 0.3 nM 9.52 Inhibition of full length carbonic anhydrase-2 in human erythrocytes 23664215
Carbonic anhydrase 2 IC50 = 0.4 nM 9.4 In vitro inhibition against purified human erythrocyte carbonic anhydrase II was... 3560154
Carbonic anhydrase 2 Ki = 0.49 nM 9.31 In vitro binding to human erythrocyte carbonic anhydrase was determined by fluor... 3560154
Unchecked Ki = 0.69 nM 9.16 Inhibition of recombinant Vibrio cholerae carbonic anhydrase expressed in Escher... 23181552
Unchecked Ki = 0.69 nM 9.16 Inhibition of Vibrio cholerae alpha-carbonic anhydrase using CO2 as substrate pr... 26850377
Carbonic anhydrase 7 Kd = 0.71 nM 9.15 Binding affinity to human recombinant CA7 at 37 degC and pH 7.0 by thermal shift... 23394791
Carbonic anhydrase 7 Kd = 0.71 nM 9.15 Binding affinity to human recombinant carbonic anhydrase 7 by thermal shift assa... 24103428
Carbonic anhydrase 2 Kd = 0.71 nM 9.15 Binding affinity to human recombinant carbonic anhydrase 2 by thermal shift assa... 24103428
Carbonic anhydrase 7 Ki = 0.78 nM 9.11 Ki value against human carbonic anhydrase VII 15686895
Carbonic anhydrase 7 Ki = 0.8 nM 9.1 Inhibition of human recombinant full length CA7 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 7 Ki = 0.8 nM 9.1 Inhibition of human cytosolic carbonic anhydrase 7 preincubated for 15 mins at r... 23965175
Carbonic anhydrase 7 Ki = 0.8 nM 9.1 Inhibition of human cloned CA7 by stopped-flow CO2 hydration method 17125255
Carbonic anhydrase 7 Ki = 0.8 nM 9.1 Inhibition of human carbonic anhydrase 7 17475500
Carbonic anhydrase 7 Ki = 0.8 nM 9.1 Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins by... 24287559
Carbonic anhydrase 7 Ki = 0.8 nM 9.1 Inhibition of human cytosolic carbonic anhydrase 7 preincubated for 15 mins by s... 23867389
Carbonic anhydrase 7 Ki = 0.8 nM 9.1 Inhibition of human recombinant carbonic anhydrase 7 by stopped flow CO2 hydrati... 19435663
Carbonic anhydrase 7 Ki = 0.8 nM 9.1 Inhibition of human full length carbonic anhydrase 7 by stopped flow CO2 hydrase... 18359629
Carbonic anhydrase 7 Ki = 0.8 nM 9.1 Inhibition of full length human carbonic anhydrase 7 preincubated for 15 mins by... 20472429
Carbonic anhydrase 7 Ki = 0.8 nM 9.1 Inhibition of human recombinant full length CA7 by stopped flow CO2 hydration as... 19186056

Literature References

PubMed DOI Target Context # Activities
31158845 10.1038/s41586-019-1291-3 ADMET 190
- 10.5281/zenodo.13943903 ADMET 89
23159038 10.1016/j.bmc.2012.10.016 Carbonic anhydrase 12 14
18572411 10.1016/j.bmc.2008.06.005 Aquaporin-4 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
26832216 10.1016/j.bmcl.2016.01.023 Unchecked 4
18042384 10.1016/j.bmcl.2007.11.025 Unchecked 4
17646100 10.1016/j.bmcl.2007.07.019 Unchecked 4
25913118 10.1016/j.bmcl.2015.04.007 Unchecked 4
18481843 10.1021/jm800121c Unchecked 4
18242998 10.1016/j.bmc.2008.01.034 Unchecked 4
24792813 10.1016/j.bmc.2014.04.006 Unchecked 3
20014752 10.1021/tx900326k Hepatotoxicity 3
26174556 10.1016/j.bmcl.2015.06.079 Unchecked 3
25773015 10.1016/j.bmc.2015.02.045 Unchecked 3
15546717 10.1016/j.bmcl.2004.09.085 Carbonic anhydrase 3
17540563 10.1016/j.bmcl.2007.05.045 Unchecked 3
25129169 10.1016/j.bmc.2014.07.048 Unchecked 3
38150360 10.1021/acs.jmedchem.3c01020 Acanthamoeba castellanii 3
3560154 10.1021/jm00387a002 Carbonic anhydrase 2 2

Data from ChEMBL 36 via Core Engine