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Revision as of 11:20, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 477110881 of page Cyclothiazide for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'DrugBank', 'ChEMBL', 'StdInChI', 'StdInChIKey').  Latest revision as of 19:14, 5 September 2024 edit 2409:40d1:102f:60b4:8000:: (talk) Changing iupac name according to IUPAC Blue BookTags: Mobile edit Mobile web edit 
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{{short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 460111148 | verifiedrevid = 477166277
| IUPAC_name = 3-(bicyclohept-5-en-2-yl)-6-chloro-3,4-dihydro-2''H''-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide | IUPAC_name = 3-(bicyclohept-5-en-2-yl)-6-chloro-1,1-dioxo-1,2,3,4-tetrahydro-1λ<sup>6</sup>,2,4-benzothiadiazine-7-sulfonamide
| image = Cyclothiazide.png | image = Cyclothiazide.png

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
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| legal_status = Rx-only | legal_status = Rx-only
| routes_of_administration = | routes_of_administration =

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
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| elimination_half-life = | elimination_half-life =
| excretion = | excretion =

<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 4167
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 2259-96-3 | CAS_number = 2259-96-3
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| PubChem = 2910 | PubChem = 2910
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = <!-- blanked - oldvalue: DB00606 --> | DrugBank = DB00606
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 571445 | ChemSpiderID = 4535011
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = P71U09G5BW | UNII = P71U09G5BW
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| KEGG = D01256 | KEGG = D01256
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 61593 --> | ChEMBL = 61593
<!--Chemical data-->
| C=14 | H=16 | Cl=1 | N=3 | O=4 | S=2 | C=14 | H=16 | Cl=1 | N=3 | O=4 | S=2
| molecular_weight = 389.88 g/mol
| smiles = O=S(=O)(c1c(Cl)cc2c(c1)S(=O)(=O)NC(N2)C43\C=C/(C3)C4)N | smiles = O=S(=O)(c1c(Cl)cc2c(c1)S(=O)(=O)NC(N2)C43\C=C/(C3)C4)N
⚫ | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| InChI = 1/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) | 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
⚫ | InChIKey = BOCUKUHCLICSIY-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫ | StdInChIKey = BOCUKUHCLICSIY-QJWLJZLASA-N
| 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?/m1/s1
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BOCUKUHCLICSIY-IHGGMMSTSA-N
}} }}

'''Cyclothiazide''' ('''Anhydron''', '''Acquirel''', '''Doburil''', '''Fluidil''', '''Renazide''', '''Tensodiural''', '''Valmiran'''), sometimes abbreviated '''CTZ''', is a ] (]) ] and ] that was originally introduced in the United States in 1963 by ] and was subsequently also marketed in ] and ].<ref name="isbn3-88763-075-0">{{cite book | author = Swiss Pharmaceutical Society | title = Index Nominum 2000: International Drug Directory (Book with CD-ROM) | publisher = Medpharm Scientific Publishers | location = Boca Raton | year = 2000 | pages = 1932 | isbn = 978-3-88763-075-1 | url = https://books.google.com/books?id=5GpcTQD_L2oC&q=Cyclothiazide&pg=PA287}}</ref><ref name="isbn0-8155-1144-2">{{cite book | vauthors = Sittig M | title = Pharmaceutical manufacturing encyclopedia | publisher = Noyes Publications | location = Park Ridge, N.J., U.S.A | year = 1988 | pages = 1756 | isbn = 978-0-8155-1144-1 | url = https://books.google.com/books?id=X2EyLsG4bcUC&q=Cyclothiazide&pg=PA418}}</ref> Related ]s include ], ], and ].<ref name="isbn0-8493-8307-2">{{cite book | vauthors = Skolnick P, Palfreyman MG, Reynolds IJ | title = Direct and allosteric control of glutamate receptors | publisher = CRC Press | location = Boca Raton | year = 1994 | pages = 174 | isbn = 978-0-8493-8307-6 | url = https://books.google.com/books?id=Fp9RLJTt7NkC&q=Cyclothiazide&pg=PA65}}</ref>

In 1993, it was discovered that cyclothiazide is a ] of the ] and ]s, capable of reducing or essentially eliminating rapid ] of the former receptor, and potentiating AMPA-mediated ] currents by as much as 18-fold at the highest concentration tested (100 ]).<ref name="isbn0-8493-8307-2"/><ref name="pmid8103555">{{cite journal | vauthors = Yamada KA, Tang CM | title = Benzothiadiazides inhibit rapid glutamate receptor desensitization and enhance glutamatergic synaptic currents | journal = The Journal of Neuroscience | volume = 13 | issue = 9 | pages = 3904–3915 | date = September 1993 | pmid = 8103555 | pmc = 6576449 | doi = 10.1523/JNEUROSCI.13-09-03904.1993 | doi-access = free }}</ref><ref name="pmid7915948">{{cite journal | vauthors = Bertolino M, Baraldi M, Parenti C, Braghiroli D, DiBella M, Vicini S, Costa E | title = Modulation of AMPA/kainate receptors by analogues of diazoxide and cyclothiazide in thin slices of rat hippocampus | journal = Receptors & Channels | volume = 1 | issue = 4 | pages = 267–278 | year = 1993 | pmid = 7915948 }}</ref><ref name="isbn3-540-22568-4">{{cite book | vauthors = Parsons CG, Danysz W, Zieglgänsberger W | chapter = Excitatory Amino Acid Neurotransmission | veditors = Ströhle A, Bilkei-Gorzo A, Holsboer F | title = Anxiety and anxiolytic drugs | publisher = Springer | location = Berlin | year = 2005 | pages = 566 | isbn = 978-3-540-22568-3 | chapter-url = https://books.google.com/books?id=RDP4_sBnsl4C&q=Cyclothiazide&pg=PA256}}</ref> Additionally, in 2003, cyclothiazide was also found to act as a ] ], potently inhibiting GABA<sub>A</sub>-mediated currents.<ref name="pmid14534329">{{cite journal | vauthors = Deng L, Chen G | title = Cyclothiazide potently inhibits gamma-aminobutyric acid type A receptors in addition to enhancing glutamate responses | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 100 | issue = 22 | pages = 13025–13029 | date = October 2003 | pmid = 14534329 | pmc = 240738 | doi = 10.1073/pnas.2133370100 | doi-access = free | bibcode = 2003PNAS..10013025D }}</ref> In animals it is a powerful ], robustly enhancing ] activity and inducing ]s, but without producing any apparent ].<ref name="pmid16423850">{{cite journal | vauthors = Qi J, Wang Y, Jiang M, Warren P, Chen G | title = Cyclothiazide induces robust epileptiform activity in rat hippocampal neurons both in vitro and in vivo | journal = The Journal of Physiology | volume = 571 | issue = Pt 3 | pages = 605–618 | date = March 2006 | pmid = 16423850 | pmc = 1805799 | doi = 10.1113/jphysiol.2005.103812 }}</ref><ref name="pmid20678492">{{cite journal | vauthors = Kong S, Qian B, Liu J, Fan M, Chen G, Wang Y | title = Cyclothiazide induces seizure behavior in freely moving rats | journal = Brain Research | volume = 1355 | pages = 207–213 | date = October 2010 | pmid = 20678492 | pmc = 2947190 | doi = 10.1016/j.brainres.2010.07.088 }}</ref>

Cyclothiazide has been found to act as a ] of the ].<ref name="pmid17095021">{{cite journal | vauthors = Surin A, Pshenichkin S, Grajkowska E, Surina E, Wroblewski JT | title = Cyclothiazide selectively inhibits mGluR1 receptors interacting with a common allosteric site for non-competitive antagonists | journal = Neuropharmacology | volume = 52 | issue = 3 | pages = 744–754 | date = March 2007 | pmid = 17095021 | pmc = 1876747 | doi = 10.1016/j.neuropharm.2006.09.018 }}</ref> It is selective for mGluR1 over other ]s.<ref name="pmid17095021" />

==Synthesis==
] }}</ref>]]

== See also ==
* ]

== References ==
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