Systematic (IUPAC) name | |
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3-(bicyclo[2.2.1]hept-5-en-2-yl)-6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide | |
Clinical data | |
Pregnancy cat. | ? |
Legal status | ℞ Prescription only |
Identifiers | |
CAS number | 2259-96-3 |
ATC code | C03AA09 |
PubChem | CID 2910 |
DrugBank | DB00606 |
ChemSpider | 4535011 |
UNII | P71U09G5BW |
KEGG | D01256 |
ChEMBL | CHEMBL61593 |
Chemical data | |
Formula | C14H16ClN3O4S2 |
Mol. mass | 389.88 g/mol |
SMILES | eMolecules & PubChem |
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Cyclothiazide (Anhydron, Acquirel, Doburil, Fluidil, Renazide, Tensodiural, Valmiran) is a benzothiadiazide (thiazide) diuretic and antihypertensive that was originally introduced in the United States in 1963 by Eli Lilly and was subsequently also marketed in Europe and Japan.[1][2] Related drugs include diazoxide, hydrochlorothiazide, and chlorothiazide.[3]
In 1993, it was discovered that cyclothiazide is a positive allosteric modulator of the AMPA receptor, capable of reducing or essentially eliminating rapid desensitization of the receptor, and potentiating glutamate currents by as much as 18-fold at the highest concentration tested (100 μM).[3][4][5][6] Additionally, in 2003, cyclothiazide was also found to act as a GABAA receptor negative allosteric modulator, potently inhibiting GABAA-mediated currents.[7] In animals it is a powerful convulsant, robustly enhancing epileptiform activity and inducing seizures, but without producing any apparent neuronal death.[8][9]
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