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Compound Detail

CHEMBL20

ACETAZOLAMIDE
💊 Approved Drug
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💊 Approved Drug
CC(=O)Nc1nnc(S(N)(=O)=O)s1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL20
Name ACETAZOLAMIDE
Phase Approved
Structure Type MOL
InChI Key BZKPWHYZMXOIDC-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Acetamox Acetazolamida Acetazolamide Acetazolamidum Atenezo Defiltran Diamox Diamox sr Didoc Diuriwas Donmox Edemox +6 more
50
Targets
2,613
Activities
3
Assay Types
11
PK Parameters
20
Publications
18
Known Names
20
Indications
4
Mechanisms

Molecular Properties

222.2
MW (Da)
-0.86
ALogP
6
HBA
2
HBD
115.0
PSA (Ų)
0.63
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1953
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -zolamide

Extended Properties

Molecular Formula C4H6N4O3S2
MW 222.25
Aromatic Rings 1
Heavy Atoms 13
NP-Likeness -2.49

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Carbonic anhydrase I inhibitor INHIBITOR Carbonic anhydrase 1 ✓ ✓
Carbonic anhydrase II inhibitor INHIBITOR Carbonic anhydrase 2 ✓ ✓
Carbonic anhydrase XII inhibitor INHIBITOR Carbonic anhydrase 12 ✓ ✓
Carbonic anhydrase IV inhibitor INHIBITOR Carbonic anhydrase 4 ✓ ✓

Indications

Altitude Sickness Edema Epilepsy Glaucoma Glaucoma, Angle-Closure Heart Failure Heart Failure Seizures Apnea Carcinoma, Hepatocellular Hydrocephalus, Normal Pressure Pseudotumor Cerebri Chronic Pain Cysticercosis Helicobacter Infections Hypertension, Pulmonary Kidney Diseases Landau-Kleffner Syndrome Macular Edema Multiple Sclerosis

ATC Classification

S01EC01
acetazolamide
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Drug Warnings

Black Box Warning
dermatological toxicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States

Activity Summary

Ki 2,284 meas. best 10.22
IC50 229 meas. best 8.59
Kd 100 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 9
CHEMBL3594
 Ki 10.22 7.6108 0.1 333
Carbonic anhydrase 2
CHEMBL205
 Ki 9.46 7.8349 0.3 493
Carbonic anhydrase 1
CHEMBL261
 Ki 9.13 6.5564 0.7 474
Carbonic anhydrase
CHEMBL2095180
 Ki 9.1 9.1 0.8 1
Unchecked
CHEMBL612545
 Ki 9.05 7.0242 0.9 206
Carbonic anhydrase 9
CHEMBL3594
 Kd 9.0 8.0173 1.0 11
Carbonic anhydrase V
CHEMBL2111457
 Ki 8.74 8.74 1.8 1
Carbonic anhydrase 7
CHEMBL2326
 Ki 8.7 8.5403 2.0 88
Carbonic anhydrase 14
CHEMBL3510
 Kd 8.67 7.942 2.1 5
Carbonic anhydrase 7
CHEMBL2326
 Kd 8.62 7.9113 2.4 8
Carbonic anhydrase 12
CHEMBL3242
 Ki 8.6 8.2283 2.5 258
Carbonic anhydrase 2
CHEMBL205
 Kd 8.59 7.745 2.6 16
Carbonic anhydrase 9
CHEMBL3594
 IC50 8.59 6.776 2.6 73
Carbonic anhydrase 3
CHEMBL2885
 Ki 8.51 5.335 3.1 6
Carbonic anhydrase 2
CHEMBL205
 IC50 8.47 7.2133 3.4 79
Carbonic anhydrase, alpha family
CHEMBL3621035
 Ki 8.37 8.37 4.3 1
Carbonate dehydratase
CHEMBL3745586
 Ki 8.35 8.35 4.5 1
Carbonic anhydrase 14
CHEMBL3510
 Ki 8.24 7.3936 5.7 44
Carbonic anhydrase 12
CHEMBL3242
 IC50 8.24 6.9686 5.7 7
Carbonic anhydrase-related protein 11
CHEMBL2420
 Ki 8.24 8.24 5.7 1
Carbonic anhydrase 1
CHEMBL261
 IC50 8.24 6.4619 5.8 31
Carbonic anhydrase 13
CHEMBL3912
 Ki 8.24 7.7928 5.7 18
Unchecked
CHEMBL612545
 IC50 8.15 6.6964 7.0 14
Carbonic anhydrase 4
CHEMBL3729
 Ki 8.07 7.1132 8.6 94
Carbonic anhydrase 2
CHEMBL6068
 Ki 8.05 8.05 9.0 1
Carbonic anhydrase 6
CHEMBL3025
 Kd 8.01 7.0483 9.8 6
Carbonic anhydrase 2
CHEMBL1697676
 Ki 8.0 7.9867 10.0 9
Carbonic anhydrase 13
CHEMBL3912
 Kd 8.0 7.3792 10.0 12
Carbonic anhydrase 6
CHEMBL3025
 Ki 7.96 7.7852 11.0 31
Carbonic anhydrase
CHEMBL6185
 Ki 7.96 7.96 11.0 5
PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)
CHEMBL5767
 Ki 7.92 7.14 12.0 6
Carbonic anhydrase 4
CHEMBL3729
 Kd 7.92 7.368 12.0 5
Alpha carbonic anhydrase
CHEMBL1075028
 Ki 7.8 7.8 16.0 2
Carbonic anhydrase
CHEMBL2096971
 IC50 7.8 7.8 16.0 1
Carbonic anhydrase 7
CHEMBL2216
 Ki 7.8 7.8 16.0 1
Carbonic anhydrase 13
CHEMBL2186
 Ki 7.77 7.77 17.0 15
Carbonic anhydrase
CHEMBL2095180
 IC50 7.7 7.03 20.0 2
Carbonic anhydrase
CHEMBL4211
 Ki 7.7 7.69 20.0 2
Carbonic anhydrase 12
CHEMBL3242
 Kd 7.62 7.061 24.0 10
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Ki 7.61 7.2 24.6 38
Carbonic anhydrase
CHEMBL2401609
 Ki 7.57 7.57 27.0 4
AGAP002992-PA
CHEMBL3399914
 Ki 7.56 7.56 27.3 1
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Kd 7.47 6.89 34.0 5
Carbonic anhydrase 14
CHEMBL3510
 IC50 7.32 6.985 48.0 2
Astrosclerin-3
CHEMBL1944499
 Ki 7.29 7.29 51.0 2
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 7.22 7.1354 60.0 50
Carbonic anhydrase
CHEMBL3932
 Ki 7.22 6.9767 60.0 6
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 IC50 7.16 7.16 69.0 1
Carbonic anhydrase 4
CHEMBL281
 IC50 7.16 7.16 70.0 2
Carbonic anhydrase 4
CHEMBL281
 Ki 7.16 6.9263 70.0 16

Pharmacokinetic Data

Parameter Value Units Species
CL 0.65 mL.min-1.kg-1 Homo sapiens
CL 0.65 mL.min-1.kg-1 Homo sapiens
Fu 0.04 - Homo sapiens
Ka 3.4 10'6/M/s Homo sapiens
Ka 2.8 10'7/M/s Homo sapiens
Ka 3.7 10'6/M/s Homo sapiens
Ka 2.2 10'7/M/s Homo sapiens
Ka 4.1 10'5/M/s Homo sapiens
Ka 1.5 10'6/M/s Homo sapiens
MRT 9.5 hr Homo sapiens
T1/2 13.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 9 Ki = 0.06 nM 10.22 Inhibition of human carbonic anhydrase-9 preincubated for 15 mins by stopped flo... 26682703
Carbonic anhydrase 2 Ki = 0.3434 nM 9.46 Binding affinity to human CA2 assessed as inhibition constant using 4-nitropheny... 33121862
Carbonic anhydrase 1 Ki = 0.7472 nM 9.13 Binding affinity to human CA1 assessed as inhibition constant using 4-nitropheny... 33121862
Carbonic anhydrase Ki = 0.8 nM 9.1 Compound was evaluated for the inhibition of Carbonic anhydrase (Non competitive... 3735316
Unchecked Ki = 0.9 nM 9.05 Inhibition of Sulfurihydrogenibium azorense alpha-carbonic anhydrase preincubate... 23072866
Unchecked Ki = 0.9 nM 9.05 Inhibition of Sulfurihydrogenibium azorense carbonic anhydrase preincubated for ... 23078755
Unchecked Ki = 0.9 nM 9.05 Inhibition of Sulfurihydrogenibium azorense alpha-carbonic anhydrase preincubate... 24332658
Unchecked Ki = 0.9 nM 9.05 Inhibition of recombinant Sulfurihydrogenibium yellostonense alpha-carbonic anhy... 26972117
Carbonic anhydrase 2 Ki = 0.94 nM 9.03 Inhibition of human CAH2 expressed in Escherichia coli BL21 (DE3) by stopped flo... 33523653
Carbonic anhydrase 9 Kd = 1.0 nM 9.0 Binding affinity to human CA9 catalytic domain expressed in mammalian expression... 29466001
Carbonic anhydrase V Ki = 1.8 nM 8.74 Mean inhibitory constant towards human carbonic anhydrase V determined by spectr... 15837316
Carbonic anhydrase 7 Ki = 2.0 nM 8.7 Inhibition of human CA7 by stopped-flow CO2 hydrase assay 28277280
Carbonic anhydrase 14 Kd = 2.13 nM 8.67 Binding affinity to recombinant human N-terminal His6-tagged carbonic anhydrase ... 29305297
Carbonic anhydrase 7 Kd = 2.4 nM 8.62 Binding affinity to recombinant human carbonic anhydrase 7 expressed in Escheric... 31740053
Carbonic anhydrase 7 Ki = 2.5 nM 8.6 Inhibition of human recombinant carbonic anhydrase 7 assessed as CO2 hydration p... 30015076
Carbonic anhydrase 7 Ki = 2.5 nM 8.6 Inhibition of human carbonic anhydrase 7 incubated for 15 mins prior to testing ... 29803994
Carbonic anhydrase 12 Ki = 2.5 nM 8.6 Inhibition of human carbonic anhydrase 12 assessed as reduction in CO2 hydration... 31413806
Carbonic anhydrase 7 Ki = 2.5 nM 8.6 Inhibition of recombinant full length human carbonic anhydrase-7 assessed as red... 30530195
Carbonic anhydrase 7 Ki = 2.5 nM 8.6 Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins by... 31476557
Carbonic anhydrase 7 Ki = 2.5 nM 8.6 Inhibition of recombinant human carbonic anhydrase 7 incubated for 6 hrs prior t... 32031797

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1419
- 10.6019/CHEMBL3885881 Rattus norvegicus 455
18295485 10.1016/j.bmcl.2008.02.008 Carbonic anhydrase 9 50
17544174 10.1016/j.ejmech.2007.03.037 No relevant target 38
18295485 10.1016/j.bmcl.2008.02.008 Carbonic anhydrase 2 25
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
28658574 10.1021/acs.jmedchem.7b00766 HT-29 12
33121862 10.1016/j.ejmech.2020.112923 Carbonic anhydrase 2 12
32787141 10.1021/acs.jmedchem.0c00734 Enterococcus faecium 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
33121862 10.1016/j.ejmech.2020.112923 Carbonic anhydrase 1 11
38776401 10.1021/acs.jmedchem.4c00740 Neisseria gonorrhoeae 10
32787141 10.1021/acs.jmedchem.0c00734 Unchecked 10
37077393 10.1021/acsmedchemlett.3c00032 Enterococcus faecium 10
38776401 10.1021/acs.jmedchem.4c00740 Unchecked 9
31629164 10.1016/j.ejmech.2019.111768 Carbonic anhydrase 12 9
31629164 10.1016/j.ejmech.2019.111768 Carbonic anhydrase 9 9
31629164 10.1016/j.ejmech.2019.111768 Carbonic anhydrase 1 9
31629164 10.1016/j.ejmech.2019.111768 Carbonic anhydrase 2 9
17482815 10.1016/j.bmcl.2007.04.063 Unchecked 8

Data from ChEMBL 36 via Core Engine