U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of CYCLOTHIAZIDE

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
Molecular Formula C14H16ClN3O4S2
Molecular Weight 389.878
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

CNS Active
3913
Sources: www.ncbi.nlm.nih.gov/pubmed/21269843
Curator's Comment: Cyclothiazide evokes epileptiform activities in hippocampal neurons and induces seizure behavior.

Originator

Approval Year

1963
70
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
ANHYDRON

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT3
642

OAT1
599

OAT2
145

OAT4
146
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OAT4
146
 no [IC50 >5000 uM]
OAT3
644
 yes [IC50 27.9 uM]
OAT2
147
 yes [IC50 39.2 uM]
OAT1
603
 yes [IC50 84.3 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Antihypertensive, saluretic and hypokalaemic effects of cyclothiazide in comparison with hydrochlorthiazide with amiloride supplement.
1982
Benzothiadiazides inhibit rapid glutamate receptor desensitization and enhance glutamatergic synaptic currents.
1993 Sep
Similar increases in extracellular lactic acid in the limbic system during epileptic and/or olfactory stimulation.
2000
Novel AMPA receptor potentiators LY392098 and LY404187: effects on recombinant human AMPA receptors in vitro.
2001 Jun
Patents

Patents

WO1998010786 A3
1

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:35:08 GMT 2023
Edited
by admin
on Fri Dec 15 16:35:08 GMT 2023
Record UNII
P71U09G5BW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLOTHIAZIDE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
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
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
WHO-VATC QC03AB09
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
WHO-ATC C03AB09
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
WHO-VATC QC03AA09
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
NCI_THESAURUS C49185
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
Code System Code Type Description
FDA UNII
P71U09G5BW
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
INN
1138
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
ECHA (EC/EINECS)
218-859-7
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID3022871
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
CAS
2259-96-3
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
NSC
758431
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
ChEMBL
CHEMBL61593
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
MESH
C004639
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
WIKIPEDIA
CYCLOTHIAZIDE
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
MERCK INDEX
m4022
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
761
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
CHEBI
31448
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
SMS_ID
100000083757
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
NCI_THESAURUS
C65358
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
PUBCHEM
2910
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
RXCUI
22033
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY RxNorm
EVMPD
SUB06864MIG
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
DRUG BANK
DB00606
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
HSDB
3310
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
RS_ITEM_NUM
1159008
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
IUPHAR
4167
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
Related Record Type Details
OAT-2
TRANSPORTER -> INHIBITOR
OAT-3
TRANSPORTER -> INHIBITOR
AMPA-SELECTIVE GLUTAMATE RECEPTOR 2
TARGET->POSITIVE ALLOSTERIC MODULATOR (PAM)
OAT-1
TRANSPORTER -> INHIBITOR
Related Record Type Details
Structure of CYCLOTHIAZIDE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966