Cyclothiazide

Cyclothiazide

Clinical data

ATC code
C03AA09 (WHO)

Legal status

Legal status

℞ (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 Y

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?)  (verify)

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 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 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]
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[edit]

Cyclothiazide synthesis:[11] E. Müller, K. Hasspacher, U.S. Patent 3,275,625 (1966 to Boehringer Ingelheim).

References[edit]

^ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 1932. ISBN 3-88763-075-0. 
^ Sittig,
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