Cyclothiazide

Cyclothiazide
Clinical data

ATC code	C03AA09 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 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
CAS Number	2259-96-3^Y
PubChem CID	2910
IUPHAR/BPS	4167
DrugBank	DB00606^N
ChemSpider	4535011^N
UNII	P71U09G5BW
KEGG	D01256^Y
ChEMBL	CHEMBL61593^N
ECHA InfoCard	100.017.146
Chemical and physical data
Formula	C₁₄H₁₆ClN₃O₄S₂
Molar mass	389.88 g/mol
3D model (Jmol)	Interactive image
SMILES O=S(=O)(c1c(Cl)cc2c(c1)S(=O)(=O)NC(N2)C4[C@@H]3\C=C/[C@@H](C3)C4)N
InChI 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)/t7-,8+,9?,14?/m0/s1^N Key:BOCUKUHCLICSIY-QJWLJZLASA-N^N
^NY (what is this?)

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. Related drugs include diazoxide, hydrochlorothiazide, and chlorothiazide.

In 1993, it was discovered that cyclothiazide is a positive allosteric modulator of the AMPA and kainate receptors, capable of reducing or essentially eliminating rapid desensitization of the former receptor, and potentiating AMPA-mediated glutamate currents by as much as 18-fold at the highest concentration tested (100 μM). Additionally, in 2003, cyclothiazide was also found to act as a GABA_A receptor negative allosteric modulator, potently inhibiting GABA_A-mediated currents. In animals it is a powerful convulsant, robustly enhancing epileptiform activity and inducing seizures, but without producing any apparent neuronal death.