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Compound Detail

CHEMBL19

METHAZOLAMIDE
💊 Approved Drug
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💊 Approved Drug
CC(=O)/N=c1/sc(S(N)(=O)=O)nn1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL19
Name METHAZOLAMIDE
Phase Approved
Structure Type MOL
InChI Key FLOSMHQXBMRNHR-QPJJXVBHSA-N
Therapeutic ✓ Yes

Known Names

L-584601 Metazolamida Methazolamide Methenamide Neptazane Neptazaneat NSC-758426 VVP-808 VVP808
35
Targets
444
Activities
3
Assay Types
0
PK Parameters
20
Publications
9
Known Names
5
Indications
4
Mechanisms

Molecular Properties

236.3
MW (Da)
-1.42
ALogP
6
HBA
1
HBD
107.4
PSA (Ų)
0.64
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1959
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -zolamide

Extended Properties

Molecular Formula C5H8N4O3S2
MW 236.28
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness -1.87

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Carbonic anhydrase VII inhibitor INHIBITOR Carbonic anhydrase 7 ✓ ✓
Carbonic anhydrase I inhibitor INHIBITOR Carbonic anhydrase 1 ✓ ✓
Carbonic anhydrase II inhibitor INHIBITOR Carbonic anhydrase 2 ✓ ✓
Carbonic anhydrase IV inhibitor INHIBITOR Carbonic anhydrase 4 ✓ ✓

Indications

Glaucoma Glaucoma, Open-Angle Essential Tremor Uterine Cervical Neoplasms Altitude Sickness

ATC Classification

S01EC05
methazolamide
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

Ki 428 meas. best 8.96
IC50 15 meas. best 9.6
Kd 1 meas. best 7.26

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 9
CHEMBL3594
 IC50 9.6 8.585 0.2 2
Carbonic anhydrase 3
CHEMBL2885
 Ki 8.96 8.96 1.1 1
Carbonic anhydrase 7
CHEMBL2326
 Ki 8.68 8.68 2.1 10
Carbonic anhydrase V
CHEMBL2111457
 Ki 8.6 8.6 2.5 1
Carbonic anhydrase 12
CHEMBL3242
 Ki 8.47 8.43 3.4 25
Unchecked
CHEMBL612545
 Ki 8.44 6.6874 3.6 50
Carbonic anhydrase 2
CHEMBL205
 IC50 8.32 7.8433 4.8 6
Carbonate dehydratase
CHEMBL3745586
 Ki 8.09 8.09 8.2 1
Carbonic anhydrase 2
CHEMBL205
 Ki 8.05 7.8462 9.0 103
Carbonic anhydrase 6
CHEMBL3025
 Ki 8.0 8.0 10.0 7
Carbonic anhydrase 1
CHEMBL261
 IC50 7.85 7.405 14.0 4
Carbonic anhydrase 1
CHEMBL261
 Ki 7.85 6.8733 14.0 96
Carbonic anhydrase 13
CHEMBL3912
 Ki 7.72 7.72 19.0 1
Carbonic anhydrase 13
CHEMBL2186
 Ki 7.72 7.72 19.0 7
Carbonic anhydrase
CHEMBL2095180
 IC50 7.7 7.7 20.0 1
Alpha carbonic anhydrase
CHEMBL1075028
 Ki 7.67 7.67 21.2 2
Carbonic anhydrase, alpha family
CHEMBL3621035
 Ki 7.58 7.58 26.5 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 7.57 7.5088 27.0 49
Carbonic anhydrase 4
CHEMBL281
 Ki 7.44 7.0438 36.0 16
Carbonic anhydrase 4
CHEMBL281
 IC50 7.44 7.44 36.0 2
Carbonic anhydrase 14
CHEMBL3510
 Ki 7.37 7.37 43.0 9
Carbonic anhydrase 2
CHEMBL205
 Kd 7.26 7.26 54.8 1
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Ki 7.21 7.21 62.0 8
Carbonic anhydrase 2
CHEMBL1697676
 Ki 7.2 7.2 63.0 1
Carbonic anhydrase 15
CHEMBL5973
 Ki 7.19 7.19 65.0 1
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 7.19 7.19 65.0 8
Carbonic anhydrase
CHEMBL6185
 Ki 6.93 6.93 118.0 1
Carbonic anhydrase
CHEMBL5931
 Ki 6.92 6.92 119.0 1
Carbonic anhydrase
CHEMBL1649055
 Ki 6.88 6.88 132.0 1
Carbonic anhydrase
CHEMBL3932
 Ki 6.85 6.81 140.0 2
Carbonic anhydrase
CHEMBL4211
 Ki 6.77 6.71 171.0 2
Delta carbonic anhydrase
CHEMBL3097982
 Ki 6.77 6.77 170.0 1
AGAP002992-PA
CHEMBL3399914
 Ki 6.74 6.74 184.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 6.62 5.3863 240.0 8
Astrosclerin-3
CHEMBL1944499
 Ki 6.49 6.49 326.0 1
Carbonic anhydrase
CHEMBL5337
 Ki 6.32 6.32 484.0 2
PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)
CHEMBL5767
 Ki 6.25 6.25 562.0 1
Carbonic anhydrase 2
CHEMBL6068
 Ki 6.18 6.18 660.0 1
Beta-carbonic anhydrase 1
CHEMBL5631
 Ki 6.11 6.11 781.0 2
Carbonic anhydrase
CHEMBL3926
 Ki 4.49 4.49 32100.0 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 recombinant human carbonic anhydrase 9 after 15 mins by stopped fl... 23429054
Carbonic anhydrase 3 Ki = 1.1 nM 8.96 Inhibition of human carbonic anhydrase 3 17475500
Carbonic anhydrase 7 Ki = 2.1 nM 8.68 Inhibition of human recombinant CA7 assessed as inhibition constant incubated fo... 38436571
Carbonic anhydrase 7 Ki = 2.1 nM 8.68 Inhibition of human cytosolic carbonic anhydrase 7 preincubated for 15 mins at r... 23965175
Carbonic anhydrase 7 Ki = 2.1 nM 8.68 Inhibition of human cytosolic carbonic anhydrase 7 preincubated for 15 mins by s... 23867389
Carbonic anhydrase 7 Ki = 2.1 nM 8.68 Inhibition of human recombinant cytosolic carbonic anhydrase 7 preincubated for ... 21620713
Carbonic anhydrase 7 Ki = 2.1 nM 8.68 Inhibition of human recombinant full length CA7 by stopped-flow CO2 hydration me... 19119014
Carbonic anhydrase 7 Ki = 2.1 nM 8.68 Inhibition of human recombinant full length CA7 by stopped flow CO2 hydration as... 19186056
Carbonic anhydrase 7 Ki = 2.1 nM 8.68 Inhibition of human full length carbonic anhydrase 7 by stopped flow CO2 hydrase... 18359629
Carbonic anhydrase 7 Ki = 2.1 nM 8.68 Inhibition of human carbonic anhydrase 7 17475500
Carbonic anhydrase 7 Ki = 2.1 nM 8.68 Inhibition of human cloned CA7 by stopped-flow CO2 hydration method 17125255
Carbonic anhydrase 7 Ki = 2.1 nM 8.68 Ki value against human carbonic anhydrase VII 15686895
Carbonic anhydrase V Ki = 2.5 nM 8.6 Mean inhibitory constant towards human carbonic anhydrase V determined by spectr... 15837316
Carbonic anhydrase 12 Ki = 3.4 nM 8.47 Ki value against human carbonic anhydrase XII (hCA XII) 15686894
Carbonic anhydrase 12 Ki = 3.4 nM 8.47 Inhibition of human catalytic domain carbonic anhydrase 12 by stopped flow CO2 h... 18359629
Carbonic anhydrase 12 Ki = 3.4 nM 8.47 Inhibition of human recombinant CA12 by CO2 hydration assay 17157501
Carbonic anhydrase 12 Ki = 3.4 nM 8.47 Inhibition of human carbonic anhydrase 12 17475500
Carbonic anhydrase 12 Ki = 3.4 nM 8.47 Inhibition of human recombinant CA12 by CO2 hydration stopped flow assay 18042384
Carbonic anhydrase 12 Ki = 3.4 nM 8.47 Inhibition of catalytic domain of human cloned CA12 by stopped-flow CO2 hydratio... 17125255
Carbonic anhydrase 12 Ki = 3.4 nM 8.47 Inhibition of human recombinant CA12 catalytic domain by stopped flow CO2 hydrat... 19186056

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
16033263 10.1021/jm0501073 ADMET 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
10649985 10.1021/jm990479+ ADMET 6
15084132 10.1021/jm031079w Unchecked 6
18242998 10.1016/j.bmc.2008.01.034 Unchecked 4
26832216 10.1016/j.bmcl.2016.01.023 Unchecked 4
18042384 10.1016/j.bmcl.2007.11.025 Unchecked 4
25913118 10.1016/j.bmcl.2015.04.007 Unchecked 4
11784136 10.1021/jm0109199 Mus musculus 4
18481843 10.1021/jm800121c Unchecked 4
17540563 10.1016/j.bmcl.2007.05.045 Unchecked 3
15546717 10.1016/j.bmcl.2004.09.085 Carbonic anhydrase 3
24792813 10.1016/j.bmc.2014.04.006 Unchecked 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
25773015 10.1016/j.bmc.2015.02.045 Unchecked 3
26174556 10.1016/j.bmcl.2015.06.079 Unchecked 3
25129169 10.1016/j.bmc.2014.07.048 Unchecked 3

Data from ChEMBL 36 via Core Engine