CYCLOTHIAZIDE

Details

Stereochemistry	UNKNOWN
Molecular Formula	C14H16ClN3O4S2
Molecular Weight	389.878
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NS(=O)(=O)C1=CC2=C(NC(NS2(=O)=O)C3CC4CC3C=C4)C=C1Cl

InChI

InChIKey=BOCUKUHCLICSIY-UHFFFAOYSA-N

InChI=1S/C14H16ClN3O4S2/c15-10-5-11-13(6-12(10)23(16,19)20)24(21,22)18-14(17-11)9-4-7-1-2-8(9)3-7/h1-2,5-9,14,17-18H,3-4H2,(H2,16,19,20)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10653443
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/14534329

Cyclothiazide was presumably developed by Eli Lilly for the treatment of hypertension. It is believed that the drug, which belongs to the class of thiazide diuretics, exerts its action by inhibitin sodium reabsorption in the renal tubules. In 1993 it was discovered that cyclothiazide stimulates AMPA receptors thus inducing seizure behavior.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
renal sodium ion absorption 3 Target ID: GO:0070294 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10653443	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18420703	Primary		Approved 8429	ANHYDRON Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT3 642 OAT1 599 OAT2 145 OAT4 146

Drug as perpetrator

Target	Modality	Activity
OAT4 146	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14610216/	no [IC50 >5000 uM]
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14610216/	yes [IC50 27.9 uM]
OAT2 147	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14610216/	yes [IC50 39.2 uM]
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14610216/	yes [IC50 84.3 uM]

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31448	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31448
MolPort	MolPort-003-666-800	https://www.molport.com/shop/molecule-link/MolPort-003-666-800
eMolecules	536638	https://www.emolecules.com/cgi-bin/more?vid=536638

PubMed

Title	Date	PubMed
Antihypertensive, saluretic and hypokalaemic effects of cyclothiazide in comparison with hydrochlorthiazide with amiloride supplement.	1982	7128662
Benzothiadiazides inhibit rapid glutamate receptor desensitization and enhance glutamatergic synaptic currents.	1993 Sep	8103555
Cyclothiazide potently inhibits gamma-aminobutyric acid type A receptors in addition to enhancing glutamate responses.	2003 Oct 28	14534329

Patents

Sample Use Guides

In Vivo Use Guide

2.5 mg daily.

Route of Administration: Oral

In Vitro Use Guide

Cyclothiazide was added at concentration of 100 uM to rat medullary slices to test its effect on AMPA receptor channel desensitization.

Name

Type

Language

CYCLOTHIAZIDE

Official Name

English

Cyclothiazide [WHO-DD]

Common Name

English

CYCLOTHIAZIDE [JAN]

Common Name

English

FLUIDIL

Brand Name

English

CYCLOTHIAZIDE [MI]

Common Name

English

CYCLOTHIAZIDE [HSDB]

Common Name

English

NSC-758431

Code

English

ANHYDRON

Brand Name

English

CYCLOTHIAZIDE [ORANGE BOOK]

Common Name

English

2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE, 3-BICYCLO(2.2.1)HEPT-5-EN-2-YL-6-CHLORO-3,4-DIHYDRO-, 1,1-DIOXIDE

Systematic Name

English

cyclothiazide [INN]

Common Name

English

35483

Code

English

CYCLOTHIAZIDE [MART.]

Common Name

English

6-Chloro-3,4-dihydro-3-(5-norbornen-2-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

Systematic Name

English

CYCLOTHIAZIDE [USAN]

Common Name

English

CYCLOTHIAZIDE [VANDF]

Common Name

English

CYCLOTHIAZIDE [USP-RS]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C03AA09