Cyclothiazide

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Chemical compound

title: "Cyclothiazide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["diuretics", "sulfonamides", "ampa-receptor-positive-allosteric-modulators", "kainate-receptor-agonists", "benzothiadiazines", "chloroarenes", "gabaa-receptor-negative-allosteric-modulators", "carbonic-anhydrase-inhibitors", "convulsants", "mglu1-receptor-antagonists", "alkene-derivatives"] description: "Chemical compound" topic_path: "general/diuretics" source: "https://en.wikipedia.org/wiki/Cyclothiazide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | verifiedrevid = 477166277 | 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 | image = Cyclothiazide.png | image_class = skin-invert-image | tradename = | pregnancy_category = | legal_status = Rx-only | routes_of_administration = | bioavailability = | metabolism = | elimination_half-life = | excretion = | IUPHAR_ligand = 4167 | CAS_number_Ref = | CAS_number = 2259-96-3 | ATC_prefix = C03 | ATC_suffix = AA09 | PubChem = 2910 | DrugBank_Ref = | DrugBank = DB00606 | ChemSpiderID_Ref = | ChemSpiderID = 4535011 | UNII_Ref = | UNII = P71U09G5BW | KEGG_Ref = | KEGG = D01256 | ChEMBL_Ref = | ChEMBL = 61593 | C=14 | H=16 | Cl=1 | N=3 | O=4 | S=2 | smiles = O=S(=O)(c1c(Cl)cc2c(c1)S(=O)(=O)NC(N2)C4[C@@H]3\C=C/C@@HC4)N | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = BOCUKUHCLICSIY-QJWLJZLASA-N

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. 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 GABAA receptor negative allosteric modulator, potently inhibiting GABAA-mediated currents. In animals it is a powerful convulsant, robustly enhancing epileptiform activity and inducing seizures, but without producing any apparent neuronal death.

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

Synthesis

::figure[src="https://upload.wikimedia.org/wikipedia/commons/f/f1/Cyclothiazide_synthesis.svg" caption="assign1 = [[Boehringer Ingelheim]] }}"] ::

References

References

  1. Swiss Pharmaceutical Society. (2000). "Index Nominum 2000: International Drug Directory (Book with CD-ROM)". Medpharm Scientific Publishers.
  2. (1988). "Pharmaceutical manufacturing encyclopedia". Noyes Publications.
  3. (1994). "Direct and allosteric control of glutamate receptors". CRC Press.
  4. (September 1993). "Benzothiadiazides inhibit rapid glutamate receptor desensitization and enhance glutamatergic synaptic currents". The Journal of Neuroscience.
  5. (1993). "Modulation of AMPA/kainate receptors by analogues of diazoxide and cyclothiazide in thin slices of rat hippocampus". Receptors & Channels.
  6. (2005). "Anxiety and anxiolytic drugs". Springer.
  7. (October 2003). "Cyclothiazide potently inhibits gamma-aminobutyric acid type A receptors in addition to enhancing glutamate responses". Proceedings of the National Academy of Sciences of the United States of America.
  8. (March 2006). "Cyclothiazide induces robust epileptiform activity in rat hippocampal neurons both in vitro and in vivo". The Journal of Physiology.
  9. (October 2010). "Cyclothiazide induces seizure behavior in freely moving rats". Brain Research.
  10. (March 2007). "Cyclothiazide selectively inhibits mGluR1 receptors interacting with a common allosteric site for non-competitive antagonists". Neuropharmacology.
  11. (1961). "Diuretics. V. 3,4-Dihydro-1,2,4-benzothiadiazine 1,1-Dioxides". The Journal of Organic Chemistry.
  12. {{cite patent

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diureticssulfonamidesampa-receptor-positive-allosteric-modulatorskainate-receptor-agonistsbenzothiadiazineschloroarenesgabaa-receptor-negative-allosteric-modulatorscarbonic-anhydrase-inhibitorsconvulsantsmglu1-receptor-antagonistsalkene-derivatives