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Compound Detail

CHEMBL218490

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

Basic Information

ChEMBL ID CHEMBL218490
Name DORZOLAMIDE
Phase Approved
Structure Type MOL
InChI Key IAVUPMFITXYVAF-XPUUQOCRSA-N
Therapeutic ✓ Yes

Known Names

Dorzant Dorzolamida Dorzolamide Dorzolamide, trans-(-)- Trusopt
35
Targets
367
Activities
3
Assay Types
1
PK Parameters
20
Publications
5
Known Names
5
Indications

Molecular Properties

324.4
MW (Da)
0.61
ALogP
6
HBA
2
HBD
106.3
PSA (Ų)
0.85
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1994
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product
USAN Stem -zolamide
USAN Year 1992

Extended Properties

Molecular Formula C10H16N2O4S3
MW 324.45
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -0.51

Indications

Glaucoma Glaucoma, Open-Angle Ocular Hypertension Macular Degeneration Wet Macular Degeneration

ATC Classification

S01EC03
dorzolamide
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

Ki 354 meas. best 9.7
IC50 12 meas. best 9.74
Kd 1 meas. best 10.37

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 2
CHEMBL205
 Kd 10.37 10.37 0.0 1
Carbonic anhydrase 2
CHEMBL205
 IC50 9.74 8.8071 0.2 7
Carbonic anhydrase 2
CHEMBL205
 Ki 9.7 8.1344 0.2 91
Carbonic anhydrase 12
CHEMBL3242
 Ki 8.52 8.4632 3.0 19
Carbonic anhydrase 7
CHEMBL2326
 Ki 8.46 8.46 3.5 9
Unchecked
CHEMBL612545
 Ki 8.24 6.4548 5.7 48
Carbonic anhydrase, alpha family
CHEMBL3621035
 Ki 8.15 8.15 7.0 1
Carbonate dehydratase
CHEMBL3745586
 Ki 8.1 8.1 8.0 1
Carbonic anhydrase 6
CHEMBL3025
 Ki 8.0 7.9971 10.0 7
Androgen receptor
CHEMBL3072
 Ki 7.96 7.96 11.0 1
Carbonic anhydrase 13
CHEMBL3912
 Ki 7.75 7.75 18.0 1
Carbonic anhydrase 13
CHEMBL2186
 Ki 7.75 7.75 18.0 6
Alpha carbonic anhydrase
CHEMBL1075028
 Ki 7.74 7.74 18.1 2
Carbonic anhydrase 14
CHEMBL3510
 Ki 7.57 7.57 27.0 7
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Ki 7.48 7.48 33.0 5
Carbonic anhydrase 5A, mitochondrial
CHEMBL4789
 Ki 7.38 7.38 42.0 5
Carbonic anhydrase 4
CHEMBL281
 Ki 7.37 7.365 43.0 16
Carbonic anhydrase 4
CHEMBL281
 IC50 7.37 7.37 43.0 1
Carbonic anhydrase 4
CHEMBL3729
 IC50 7.37 7.37 43.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 7.37 5.5811 43.0 9
Delta carbonic anhydrase
CHEMBL3097982
 Ki 7.3 7.3 49.6 1
Carbonic anhydrase 9
CHEMBL3594
 IC50 7.28 7.28 52.0 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 7.28 7.28 52.0 29
Carbonic anhydrase 15
CHEMBL5973
 Ki 7.21 7.21 61.0 1
Androgen receptor
CHEMBL1871
 IC50 7.19 7.19 65.0 1
Carbonic anhydrase 2
CHEMBL6068
 Ki 7.0 7.0 99.0 1
Carbonic anhydrase
CHEMBL5931
 Ki 6.96 6.96 110.0 1
Carbonic anhydrase
CHEMBL1649055
 Ki 6.95 6.95 113.0 1
PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)
CHEMBL5767
 Ki 6.86 6.86 137.0 1
AGAP002992-PA
CHEMBL3399914
 Ki 6.56 6.56 275.0 1
Astrosclerin-3
CHEMBL1944499
 Ki 6.55 6.55 280.0 1
Carbonic anhydrase
CHEMBL3932
 Ki 6.39 6.08 410.0 2
Carbonic anhydrase 1
CHEMBL261
 Ki 6.3 4.4115 500.0 67
Beta-carbonic anhydrase 1
CHEMBL5631
 Ki 6.13 6.13 744.0 2
Carbonic anhydrase
CHEMBL5337
 Ki 6.05 6.05 887.0 2
Carbonic anhydrase
CHEMBL4211
 Ki 5.37 5.365 4310.0 2
Carbonic anhydrase
CHEMBL6185
 Ki 5.18 5.18 6635.0 1
Carbonic anhydrase 3
CHEMBL2885
 Ki 5.1 5.1 8000.0 1
Carbonic anhydrase 2
CHEMBL1697676
 Ki 5.08 5.08 8347.0 1
Carbonic anhydrase
CHEMBL3926
 Ki 4.51 4.51 30700.0 1
Carbonic anhydrase 1
CHEMBL261
 IC50 4.3 4.3 50000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Tmax 1.0 hr Oryctolagus cuniculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 2 Kd = 0.043 nM 10.37 Binding affinity to human carbonic anhydrase 2 incubated for 1 hr using labeled ... 25728019
Carbonic anhydrase 2 IC50 = 0.18 nM 9.74 Tested for ability to inhibit human erythrocyte carbonic-anhydrase-II- (HCA II) ... 8295211
Carbonic anhydrase 2 IC50 = 0.18 nM 9.74 Inhibitory activity against carbonic anhydrase II 12166932
Carbonic anhydrase 2 Ki = 0.1995 nM 9.7 Inhibition of human recombinant carbonic anhydrase 2 by dansylamide (DNSA) compe... 23317571
Carbonic anhydrase 2 IC50 = 0.23 nM 9.64 Compound was evaluated for the inhibitory activity against Human Carbonic anhydr... 8164249
Carbonic anhydrase 2 Ki = 0.28 nM 9.55 Tested for ability to compete with dansylamide for binding to human erythrocyte ... 8295211
Carbonic anhydrase 2 Ki = 0.37 nM 9.43 Compound was evaluated for the affinity towards Human Carbonic anhydrase II (HCA... 8164249
Carbonic anhydrase 2 Ki = 0.37 nM 9.43 Compound was evaluated for the inhibitory constant towards Human Carbonic anhydr... 8164249
Carbonic anhydrase 2 Ki = 0.372 nM 9.43 Dissociation constant against Carbonic anhydrase II was reported in experiment 1 12166932
Carbonic anhydrase 2 IC50 = 1.1 nM 8.96 Compound was evaluated for the inhibitory activity against Human Carbonic anhydr... 8164249
Carbonic anhydrase 2 Ki = 2.0 nM 8.7 Compound was evaluated for the affinity towards Human Carbonic anhydrase II (HCA... 8164249
Carbonic anhydrase 12 Ki = 3.0 nM 8.52 Inhibition of recombinant human transmembrane, tumor-associated form of carbonic... 25913118
Carbonic anhydrase 12 Ki = 3.5 nM 8.46 Inhibition of catalytic domain of human cloned CA12 by stopped-flow CO2 hydratio... 17125255
Carbonic anhydrase 7 Ki = 3.5 nM 8.46 Inhibition of human full length cytosolic carbonic anhydrase 7 after 15 mins by ... 19731956
Carbonic anhydrase 12 Ki = 3.5 nM 8.46 Inhibition of human recombinant CA12 by CO2 hydration assay 17157501
Carbonic anhydrase 7 Ki = 3.5 nM 8.46 Inhibition of human carbonic anhydrase 7 17475500
Carbonic anhydrase 12 Ki = 3.5 nM 8.46 Inhibition of human carbonic anhydrase 12 17475500
Carbonic anhydrase 7 Ki = 3.5 nM 8.46 Inhibition of human full length carbonic anhydrase 7 by stopped flow CO2 hydrase... 18359629
Carbonic anhydrase 12 Ki = 3.5 nM 8.46 Inhibition of human catalytic domain carbonic anhydrase 12 by stopped flow CO2 h... 18359629
Carbonic anhydrase 12 Ki = 3.5 nM 8.46 Inhibition of human membrane-bound carbonic anhydrase 12 catalytic domain after ... 19731956

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
11123998 10.1021/jm001051+ Oryctolagus cuniculus 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
11087579 10.1021/jm000296j Oryctolagus cuniculus 14
11425561 10.1016/s0960-894x(01)00303-1 Oryctolagus cuniculus 10
8164249 10.1021/jm00034a001 Carbonic anhydrase 2 7
10762051 10.1016/s0960-894x(00)00075-5 Oryctolagus cuniculus 7
11229775 10.1016/s0960-894x(00)00722-8 Oryctolagus cuniculus 6
8295211 10.1021/jm00028a006 Carbonic anhydrase 2 5
11906288 10.1021/jm0108202 NON-PROTEIN TARGET 4
25913118 10.1016/j.bmcl.2015.04.007 Unchecked 4
29851481 10.1021/acs.jmedchem.8b00625 Oryctolagus cuniculus 4
10479300 10.1021/jm9901879 Oryctolagus cuniculus 4
11906288 10.1021/jm0108202 Oryctolagus cuniculus 4
14611846 10.1016/s0960-894x(03)00580-8 Oryctolagus cuniculus 4
26832216 10.1016/j.bmcl.2016.01.023 Unchecked 4
24792813 10.1016/j.bmc.2014.04.006 Unchecked 3
8295211 10.1021/jm00028a006 Oryctolagus cuniculus 3
25129169 10.1016/j.bmc.2014.07.048 Unchecked 3
25773015 10.1016/j.bmc.2015.02.045 Unchecked 3

Data from ChEMBL 36 via Core Engine