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Compound Detail

CHEMBL220491

BRINZOLAMIDE
💊 Approved Drug
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💊 Approved Drug
CCN[C@H]1CN(CCCOC)S(=O)(=O)c2sc(S(N)(=O)=O)cc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL220491
Name BRINZOLAMIDE
Phase Approved
Structure Type MOL
InChI Key HCRKCZRJWPKOAR-JTQLQIEISA-N
Therapeutic ✓ Yes

Known Names

AL-4862 Azopt Brinzolamida Brinzolamide Brinzolamide component of azarga Brinzolamide component of simbrinza NSC-760050
30
Targets
256
Activities
3
Assay Types
0
PK Parameters
20
Publications
7
Known Names
4
Indications
1
Mechanisms

Molecular Properties

383.5
MW (Da)
0.09
ALogP
7
HBA
2
HBD
118.8
PSA (Ų)
0.64
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1998
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product
USAN Stem -zolamide
USAN Year 1997

Extended Properties

Molecular Formula C12H21N3O5S3
MW 383.52
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness -0.84

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Carbonic anhydrase II inhibitor INHIBITOR Carbonic anhydrase 2 ✓ ✓

Indications

Glaucoma Glaucoma, Open-Angle Ocular Hypertension Central Serous Chorioretinopathy

ATC Classification

S01EC04
brinzolamide
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S01EC54
brinzolamide, combinations
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

Ki 252 meas. best 9.9
IC50 3 meas. best 8.49
Kd 1 meas. best 10.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 2
CHEMBL205
 Kd 10.05 10.05 0.1 1
Carbonic anhydrase 2
CHEMBL205
 Ki 9.9 8.4897 0.1 65
Carbonic anhydrase 6
CHEMBL3025
 Ki 9.05 9.05 0.9 6
Unchecked
CHEMBL612545
 Ki 8.6 6.6209 2.5 44
Carbonic anhydrase 7
CHEMBL2326
 Ki 8.55 8.55 2.8 8
Carbonic anhydrase 1
CHEMBL261
 Ki 8.52 5.14 3.0 45
Carbonic anhydrase 12
CHEMBL3242
 Ki 8.52 8.5146 3.0 13
Carbonic anhydrase 2
CHEMBL205
 IC50 8.49 7.92 3.2 2
Carbonic anhydrase, alpha family
CHEMBL3621035
 Ki 8.38 8.38 4.2 1
Carbonic anhydrase 13
CHEMBL2186
 Ki 8.0 8.0 10.0 1
Carbonic anhydrase 13
CHEMBL3912
 Ki 7.96 7.96 11.0 1
Carbonate dehydratase
CHEMBL3745586
 Ki 7.91 7.91 12.3 1
Carbonic anhydrase 14
CHEMBL3510
 Ki 7.62 7.62 24.0 6
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Ki 7.52 7.52 30.0 4
AGAP002992-PA
CHEMBL3399914
 Ki 7.5 7.5 31.4 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 7.44 7.413 36.0 23
Carbonic anhydrase 4
CHEMBL281
 Ki 7.35 7.3483 45.0 6
Carbonic anhydrase 4
CHEMBL3729
 IC50 7.34 7.34 45.3 1
Alpha carbonic anhydrase
CHEMBL1075028
 Ki 7.32 7.32 48.2 2
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 7.3 7.3 50.0 4
Carbonic anhydrase 15
CHEMBL5973
 Ki 7.21 7.21 61.0 1
Carbonic anhydrase 2
CHEMBL1697676
 Ki 7.06 7.06 87.0 1
Carbonic anhydrase
CHEMBL5931
 Ki 6.94 6.94 114.0 1
Delta carbonic anhydrase
CHEMBL3097982
 Ki 6.93 6.93 118.0 1
Carbonic anhydrase 2
CHEMBL6068
 Ki 6.9 6.9 127.0 1
Carbonic anhydrase
CHEMBL1649055
 Ki 6.77 6.77 169.0 1
PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)
CHEMBL5767
 Ki 6.7 6.7 201.0 1
Carbonic anhydrase
CHEMBL4211
 Ki 6.68 6.645 210.0 2
Astrosclerin-3
CHEMBL1944499
 Ki 6.56 6.56 278.0 1
Beta-carbonic anhydrase 1
CHEMBL5631
 Ki 6.08 6.08 839.0 2
Carbonic anhydrase
CHEMBL5337
 Ki 5.96 5.96 1095.0 2
Carbonic anhydrase 4
CHEMBL3729
 Ki 5.4 5.4 3950.0 2
Carbonic anhydrase
CHEMBL6185
 Ki 5.36 5.36 4350.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 2 Kd = 0.089 nM 10.05 Binding affinity to human carbonic anhydrase 2 incubated for 1 hr using labeled ... 25728019
Carbonic anhydrase 2 Ki = 0.1259 nM 9.9 Inhibition of human recombinant carbonic anhydrase 2 by dansylamide (DNSA) compe... 23317571
Carbonic anhydrase 6 Ki = 0.9 nM 9.05 Inhibition of full length human recombinant CA VI 17228881
Carbonic anhydrase 6 Ki = 0.9 nM 9.05 Inhibition of human carbonic anhydrase 6 17475500
Carbonic anhydrase 6 Ki = 0.9 nM 9.05 Inhibition of human full length carbonic anhydrase 6 by stopped flow CO2 hydrase... 18359629
Carbonic anhydrase 6 Ki = 0.9 nM 9.05 Inhibition of human full length recombinant carbonic anhydrase 6 by stopped flow... 19193158
Carbonic anhydrase 6 Ki = 0.9 nM 9.05 Inhibition of human recombinant CA6 by stopped-flow CO2 hydration assay 21208801
Carbonic anhydrase 6 Ki = 0.9 nM 9.05 Inhibition of human carbonic anhydrase6 preincubated for 15 mins by stopped-flow... 24090602
Unchecked Ki = 2.5 nM 8.6 Inhibition of recombinant Vibrio cholerae carbonic anhydrase expressed in Escher... 23181552
Unchecked Ki = 2.5 nM 8.6 Inhibition of Vibrio cholerae alpha-carbonic anhydrase using CO2 as substrate pr... 26850377
Carbonic anhydrase 7 Ki = 2.8 nM 8.55 Inhibition of recombinant human carbonic anhydrase 7 incubated for 6 hrs prior t... 32031797
Carbonic anhydrase 7 Ki = 2.8 nM 8.55 Inhibition of human carbonic anhydrase7 preincubated for 15 mins by stopped-flow... 24090602
Carbonic anhydrase 7 Ki = 2.8 nM 8.55 Inhibition of human cytosolic carbonic anhydrase 7 preincubated for 15 mins at r... 23965175
Carbonic anhydrase 7 Ki = 2.8 nM 8.55 Inhibition of human cytosolic carbonic anhydrase 7 preincubated for 15 mins by s... 23867389
Carbonic anhydrase 7 Ki = 2.8 nM 8.55 Inhibition of human full length carbonic anhydrase 7 by stopped flow CO2 hydrase... 18359629
Carbonic anhydrase 7 Ki = 2.8 nM 8.55 Inhibition of human cloned CA7 by stopped-flow CO2 hydration method 17125255
Carbonic anhydrase 7 Ki = 2.8 nM 8.55 Ki value against human carbonic anhydrase VII 15686895
Carbonic anhydrase 7 Ki = 2.8 nM 8.55 Inhibition of human carbonic anhydrase 7 17475500
Carbonic anhydrase 2 Ki = 3.0 nM 8.52 Inhibition of human carbonic anhydrase 2 preincubated for 15 mins measured for 1... 22424239
Carbonic anhydrase 2 Ki = 3.0 nM 8.52 Inhibition of human carbonic anhydrase 2 after 15 mins by CO2 hydrase assay at p... 21377369

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
11425561 10.1016/s0960-894x(01)00303-1 Oryctolagus cuniculus 5
11906288 10.1021/jm0108202 Oryctolagus cuniculus 4
26832216 10.1016/j.bmcl.2016.01.023 Unchecked 4
14611846 10.1016/s0960-894x(03)00580-8 Oryctolagus cuniculus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
25913118 10.1016/j.bmcl.2015.04.007 Unchecked 4
25728019 10.1021/acs.jmedchem.5b00043 Oryctolagus cuniculus 4
24792813 10.1016/j.bmc.2014.04.006 Unchecked 3
38150360 10.1021/acs.jmedchem.3c01020 Acanthamoeba castellanii 3
26174556 10.1016/j.bmcl.2015.06.079 Unchecked 3
25773015 10.1016/j.bmc.2015.02.045 Unchecked 3
17540563 10.1016/j.bmcl.2007.05.045 Unchecked 3
25129169 10.1016/j.bmc.2014.07.048 Unchecked 3
24513184 10.1016/j.bmc.2014.01.031 Unchecked 2
24316122 10.1016/j.bmcl.2013.11.030 Unchecked 2
21251841 10.1016/j.bmc.2010.12.048 Unchecked 2
24314394 10.1016/j.bmcl.2013.11.021 Unchecked 2
21757360 10.1016/j.bmc.2011.06.038 Unchecked 2
19846301 10.1016/j.bmcl.2009.10.009 Carbonic anhydrase 2 2

Data from ChEMBL 36 via Core Engine