Cyclothiazide

Cyclothiazide
Cyclothiazide
Systematic (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
Clinical data
Pregnancy cat.  ?
Legal status ℞ Prescription only
Identifiers
CAS number 2259-96-3 YesY
ATC code C03AA09
PubChem CID 2910
DrugBank DB00606
ChemSpider 4535011 YesY
UNII P71U09G5BW YesY
KEGG D01256 YesY
ChEMBL CHEMBL61593 N
Chemical data
Formula C14H16ClN3O4S2 
Mol. mass 389.88 g/mol
SMILES eMolecules & PubChem
 N(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 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]

References

  1. ^ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. pp. 1932. ISBN 3-88763-075-0. http://books.google.com/books?id=5GpcTQD_L2oC&lpg=PA287&dq=Cyclothiazide&pg=PA287#v=onepage&q=Cyclothiazide&f=false. 
  2. ^ Sittig, Marshall (1988). Pharmaceutical manufacturing encyclopedia. Park Ridge, N.J., U.S.A: Noyes Publications. pp. 1756. ISBN 0-8155-1144-2. http://books.google.com/books?id=X2EyLsG4bcUC&lpg=PA418&dq=Cyclothiazide&pg=PA418#v=onepage&q&f=false. 
  3. ^ a b Skolnick, Phil; Palfreyman, Michael G.; Reynolds, Ian J. (1994). Direct and allosteric control of glutamate receptors. Boca Raton: CRC Press. pp. 174. ISBN 0-8493-8307-2. http://books.google.com/books?id=Fp9RLJTt7NkC&lpg=PA34&dq=Cyclothiazide&pg=PA65#v=onepage&q=Cyclothiazide&f=false. 
  4. ^ Yamada KA, Tang CM (September 1993). "Benzothiadiazides inhibit rapid glutamate receptor desensitization and enhance glutamatergic synaptic currents". Journal of Neuroscience 13 (9): 3904–15. PMID 8103555. http://www.jneurosci.org/cgi/pmidlookup?view=long&pmid=8103555. 
  5. ^ Bertolino M, Baraldi M, Parenti C, et al. (1993). "Modulation of AMPA/kainate receptors by analogues of diazoxide and cyclothiazide in thin slices of rat hippocampus". Receptors & Channels 1 (4): 267–78. PMID 7915948. 
  6. ^ Ströhle, Andreas; Bilkei-Gorzo, A.; Holsboer, Florian (2005). Anxiety and anxiolytic drugs. Berlin: Springer. pp. 566. ISBN 3-540-22568-4. http://books.google.com/books?id=RDP4_sBnsl4C&lpg=PA255&dq=Cyclothiazide&pg=PA256#v=onepage&q=Cyclothiazide&f=false. 
  7. ^ Deng L, Chen G (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 100 (22): 13025–9. doi:10.1073/pnas.2133370100. PMC 240738. PMID 14534329. http://www.pnas.org/cgi/pmidlookup?view=long&pmid=14534329. 
  8. ^ Qi J, Wang Y, Jiang M, Warren P, Chen G (March 2006). "Cyclothiazide induces robust epileptiform activity in rat hippocampal neurons both in vitro and in vivo". The Journal of Physiology 571 (Pt 3): 605–18. doi:10.1113/jphysiol.2005.103812. PMC 1805799. PMID 16423850. http://www.jphysiol.org/cgi/pmidlookup?view=long&pmid=16423850. 
  9. ^ Kong S, Qian B, Liu J, Fan M, Chen G, Wang Y (July 2010). "Cyclothiazide induces seizure behavior in freely moving rats". Brain Research 1355: 207–213. doi:10.1016/j.brainres.2010.07.088. PMC 2947190. PMID 20678492. http://linkinghub.elsevier.com/retrieve/pii/S0006-8993(10)01678-1. 
v · d · eAntihypertensives: diuretics (C03)
Sulfonamides
(except EA)
CA inhibitors (at PT)
Thiazide-likes (primarily DCT)
Potassium-sparing (at CD)
ESC blockers
Osmotic diuretics (PT, DL)
VAs (DCT and CD)

vaptans: Conivaptan • Mozavaptan • Satavaptan • Tolvaptan

tetracyclines: Demeclocycline
Other

M: VAS

anat(a:h/u/t/a/l,v:h/u/t/a/l)/phys/devp/cell/prot

noco/syva/cong/lyvd/tumr, sysi/epon, injr

proc, drug(C2s+n/3/4/5/7/8/9)
v · d · eSymporter inhibitors
Sodium chloride
Sodium, potassium, chloride
v · d · eGABAergics
Receptor
ligands

Agonists: Main site: Bamaluzole • Gaboxadol • Ibotenic acid • Isoguvacine • Isonipecotic acid • Muscimol (Amanita Muscaria) • Progabide • SL 75102 • Thiomuscimol • Tolgabide; Positive allosteric modulators: Barbiturates • Benzodiazepines • Carbamates • Chlormezanone • Clomethiazole • Ethanol (Alcohol) • Etomidate • Kavalactones (Kava) • Loreclezole • Metomidate • Neuroactive steroids • Nonbenzodiazepines (β-Carbolines, Cyclopyrrolones, Imidazopyridines, Pyrazolopyrimidines, etc.) • Phenols • Piperidinediones • Propanidid • Pyrazolopyridines • Quinazolinones • ROD-188 • Skullcap • Stiripentol • Valerenic acid (Valerian)
* See Template:GABAAergics for a full list of GABAA positive allosteric modulators.

Antagonists: Main site: Bicuculline • Gabazine • Pitrazepin; Negative allosteric modulators: α5IA • Bilobalide • Cicutoxin • Cyclothiazide • DMCM • Flumazenil • Flurothyl • Furosemide • L-655,708 • Oenanthotoxin • Penicillin • Pentylenetetrazol • Picrotoxin • PWZ-029 • Ro15-4513 • Sarmazenil • Suritozole • Thujone (Absinthe) • Thiocolchicoside • ZK-93426
Agonists: Main site: 1,4-Butanediol • Baclofen • GBL • GHB • GHV • GVL • Lesogaberan • Phenibut • Progabide • SKF-97,541 • Tolgabide; Positive allosteric modulators: BHF-177 • BHFF • BSPP • CGP-7930 • GS-39783
Antagonists: Main site: CGP-35348 • Phaclofen • Saclofen • SCH-50911
Agonists: Main site: CACA • CAMP • GABOB • N(4)-chloroacetylcytosine arabinoside • Progabide • Tolgabide
Antagonists: Main site: Bilobalide • TPMPA
Reuptake
inhibitors
Plasmalemmal
GAT inhibitors
CI-966 • Deramciclane • EF-1502 • Gabaculine • Guvacine • Nipecotic acid • NNC 05-2090 • SKF-89976A • SNAP-5114 • Tiagabine
Enzyme
inhibitors
GAD inhibitors
Allylglycine
GABA-T inhibitors
3-Hydrazinopropionic acid • Aminooxyacetic acid • Gabaculine • Isoniazid • Phenelzine • Phenylethylidenehydrazine • Sodium valproate • Valnoctamide • Valproate pivoxil • Valproate semisodium (Divalproex sodium) • Valproic acid • Valpromide • Vigabatrin
Others
Glutamate • Glutamine
Others
Gabapentin • L-Theanine • Picamilon • Pregabalin

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