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Compound Detail

CHEMBL61593

CYCLOTHIAZIDE
💊 Approved Drug
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💊 Approved Drug
NS(=O)(=O)c1cc2c(cc1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL61593
Name CYCLOTHIAZIDE
Phase Approved
Structure Type MOL
InChI Key BOCUKUHCLICSIY-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

35483 Anhydron Ciclotiazida Cyclothiazide Fluidil NSC-758431
8
Targets
16
Activities
2
Assay Types
0
PK Parameters
20
Publications
6
Known Names
1
Indications
1
Mechanisms

Molecular Properties

389.9
MW (Da)
1.23
ALogP
5
HBA
3
HBD
118.4
PSA (Ų)
0.66
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Discontinued
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -thiazide
USAN Year 1963

Extended Properties

Molecular Formula C14H16ClN3O4S2
MW 389.89
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness -0.67

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Thiazide-sensitive sodium-chloride cotransporter inhibitor INHIBITOR Solute carrier family 12 member 3 ✓ ✓

Indications

Cardiovascular Diseases

ATC Classification

C03AA09
cyclothiazide
Level 1: CARDIOVASCULAR SYSTEM
Level 2: DIURETICS

Activity Summary

EC50 15 meas. best 6.0
IC50 1 meas. best 5.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glutamate receptor 1
CHEMBL2009
 EC50 6.0 5.35 1000.0 4
Glutamate receptor 2
CHEMBL4016
 EC50 5.65 5.385 2240.0 2
Glutamate receptor 4
CHEMBL3190
 EC50 5.42 5.42 3800.0 2
Unchecked
CHEMBL612545
 EC50 5.41 5.2725 3910.0 4
Glutamate receptor ionotropic, AMPA
CHEMBL2093871
 IC50 5.21 5.21 6100.0 1
Glutamate receptor AMPA 1/2
CHEMBL3883294
 EC50 5.18 5.18 6600.0 1
Glutamate receptor 2
CHEMBL3503
 EC50 5.12 5.12 7600.0 1
Glutamate receptor 3
CHEMBL3595
 EC50 4.86 4.86 13700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glutamate receptor 1 EC50 = 1000.0 nM 6.0 Agonist activity at recombinant GluA1 receptor flip isoform expressed in Xenopus... 20096591
Glutamate receptor 1 EC50 = 2000.0 nM 5.7 Activity at recombinant GluA1 receptor flip isoform expressed in Xenopus oocytes... 20096591
Glutamate receptor 2 EC50 = 2240.0 nM 5.65 Activity at human recombinant GluA2 receptor flip isoform expressed in HEK293 ce... 20096591
Glutamate receptor 4 EC50 = 3800.0 nM 5.42 Tested for potentiation towards human iGluR4 receptor expressed in HEK293 cells 11087558
Glutamate receptor 4 EC50 = 3800.0 nM 5.42 Activity against human GLUR4 flip expressed in HEK293 cells assessed as glutamat... 16879964
Unchecked EC50 = 3910.0 nM 5.41 Activity at human recombinant GluA4 receptor flip isoform expressed in HEK293 ce... 20096591
Unchecked EC50 = 5000.0 nM 5.3 Activity at recombinant GluA2A4 receptor flip isoform expressed in Xenopus oocyt... 20096591
Unchecked EC50 = 5900.0 nM 5.23 Activity at recombinant GluA4 receptor flip isoform expressed in Xenopus oocytes... 20096591
Glutamate receptor ionotropic, AMPA IC50 = 6100.0 nM 5.21 Inhibition of binding to AMPA receptor from rat cerebral cortex 11462971
Glutamate receptor AMPA 1/2 EC50 = 6600.0 nM 5.18 Activity at recombinant GluA1A2 receptor flip isoform expressed in Xenopus oocyt... 20096591
Unchecked EC50 = 7100.0 nM 5.15 Activity at Wistar rat cortex AMPA receptor expressed in Xenopus laevis oocytes ... 17552506
Glutamate receptor 2 EC50 = 7600.0 nM 5.12 Agonist activity at rat flip iGluR2(Q) expressed in Xenopus laevis oocytes by wh... 18811139
Glutamate receptor 2 EC50 = 7600.0 nM 5.12 Agonist activity at human GluA2(Q)i expressed in HEK293 cells assessed as enhanc... 26653877
Glutamate receptor 1 EC50 = 10000.0 nM 5.0 Activity at recombinant GluA1 receptor flop isoform expressed in Xenopus oocytes... 20096591
Glutamate receptor 3 EC50 = 13700.0 nM 4.86 Activity at human recombinant GluA3 receptor flip isoform expressed in HEK293 ce... 20096591
Glutamate receptor 1 EC50 = 19800.0 nM 4.7 Activity at human recombinant GluA1 receptor flip isoform expressed in HEK293 ce... 20096591

Literature References

PubMed DOI Target Context # Activities
20096591 10.1016/j.bmc.2009.12.072 Glutamate receptor 1 8
20096591 10.1016/j.bmc.2009.12.072 Glutamate receptor AMPA 1/2 7
- 10.1016/S0960-894X(01)80542-4 Glutamate receptor ionotropic, AMPA 7
19338354 10.1021/jm8012882 Unchecked 6
20096591 10.1016/j.bmc.2009.12.072 Unchecked 5
31803402 10.1039/C9MD00262F Glutamate receptor ionotropic, AMPA 4
20096591 10.1016/j.bmc.2009.12.072 Glutamate receptor 3 4
17552506 10.1021/jm070120i Unchecked 4
20096591 10.1016/j.bmc.2009.12.072 Glutamate receptor AMPA 2/3 3
18980844 10.1016/j.bmc.2008.10.036 Unchecked 3
16879964 10.1016/j.bmcl.2006.07.035 Glutamate receptor 4 2
20108934 10.1021/jm901495t Oocyte 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
16879964 10.1016/j.bmcl.2006.07.035 Glutamate receptor 2 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
9685234 10.1021/jm970694v Rattus norvegicus 2
9685234 10.1021/jm970694v Glutamate receptor ionotropic, AMPA 2
- 10.1016/S0960-894X(96)00547-1 Glutamate receptor 1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
20096591 10.1016/j.bmc.2009.12.072 Glutamate receptor 2 2

Data from ChEMBL 36 via Core Engine