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-1,1-dioxo-1,2,3,4-tetrahydro-1λ6,2,4-benzothiadiazine-7-sulfonamide;
CAS Number	2259-96-3 ;
PubChem CID	2910;
IUPHAR/BPS	4167;
DrugBank	DB00606 ;
ChemSpider	4535011 ;
UNII	P71U09G5BW;
KEGG	D01256 ;
ChEMBL	ChEMBL61593 ;
CompTox Dashboard (EPA)	DTXSID3022871 ;
ECHA InfoCard	100.017.146
Chemical and physical data
Formula	C14H16ClN3O4S2
Molar mass	389.87 g·mol−1
3D model (JSmol)	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 ; Key:BOCUKUHCLICSIY-QJWLJZLASA-N ;
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Cyclothiazide (Anhydron, Acquirel, Doburil, Fluidil, Renazide, Tensodiural, Valmiran), sometimes abbreviated CTZ, 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]

Quick Facts Clinical data, ATC code ...

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).^[3]^[4]^[5]^[6] Additionally, in 2003, cyclothiazide was also found to act as a GABA_A receptor negative allosteric modulator, potently inhibiting GABA_A-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]

Cyclothiazide has been found to act as a non-competitive antagonist of the mGluR1.^[10] It is selective for mGluR1 over other metabotropic glutamate receptors.^[10]

Synthesis