Cyclothiazide: Difference between revisions

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{{Drugbox
{{Drugbox
| IUPAC_name        =  
| Verifiedfields = changed
| image            =  
| verifiedrevid = 477166277
| CAS_number        =  
| IUPAC_name = 3-(bicyclo[2.2.1]hept-5-en-2-yl)-6-chloro-3,4-dihydro-2''H''-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
| ATC_prefix        = C03
| image = Cyclothiazide.png
| ATC_suffix        = AA09
| PubChem          = 2910
| DrugBank          =
| chemical_formula  = C14H16ClN3O4S2
| molecular_weight  = 389.87754
| bioavailability  =
| protein_bound    =
| metabolism        =
| elimination_half-life =
| excretion        =
| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US      =  <!-- A / B            / C / D / X -->
| pregnancy_category= 
| legal_AU =  <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA =  <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK =  <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US =  <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status      =  
| routes_of_administration =
}}
{{CMG}}


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


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


'''Cyclothiazide''' is a [[diuretic]].
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 2259-96-3
| ATC_prefix = C03
| ATC_suffix = AA09
| PubChem = 2910
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB00606
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4535011
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = P71U09G5BW
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D01256
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 61593


<!--Chemical data-->
| 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)C4[C@@H]3\C=C/[C@@H](C3)C4)N
| 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)
| InChIKey = BOCUKUHCLICSIY-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| 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 = {{stdinchicite|changed|chemspider}}
| StdInChIKey = BOCUKUHCLICSIY-QJWLJZLASA-N
}}


{{Antihypertensives and diuretics}}
'''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 Company|Eli Lilly]] and was subsequently also marketed in [[Europe]] and [[Japan]].<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 = 3-88763-075-0 | oclc = | doi = | url = http://books.google.com/books?id=5GpcTQD_L2oC&lpg=PA287&dq=Cyclothiazide&pg=PA287#v=onepage&q=Cyclothiazide&f=false}}</ref><ref name="isbn0-8155-1144-2">{{cite book | author = Sittig, Marshall | title = Pharmaceutical manufacturing encyclopedia | publisher = Noyes Publications | location = Park Ridge, N.J., U.S.A | year = 1988 | pages = 1756 | isbn = 0-8155-1144-2 | oclc = | doi = | url = http://books.google.com/books?id=X2EyLsG4bcUC&lpg=PA418&dq=Cyclothiazide&pg=PA418#v=onepage&q&f=false}}</ref> Related [[drug]]s include [[diazoxide]], [[hydrochlorothiazide]], and [[chlorothiazide]].<ref name="isbn0-8493-8307-2">{{cite book | author = Skolnick, Phil; Palfreyman, Michael G.; Reynolds, Ian J. | title = Direct and allosteric control of glutamate receptors | publisher = CRC Press | location = Boca Raton | year = 1994 | pages = 174 | isbn = 0-8493-8307-2 | oclc = | doi = | url = http://books.google.com/books?id=Fp9RLJTt7NkC&lpg=PA34&dq=Cyclothiazide&pg=PA65#v=onepage&q=Cyclothiazide&f=false}}</ref>


In 1993, it was discovered that cyclothiazide is a [[positive allosteric modulator]] of the [[AMPA receptor]], capable of reducing or essentially eliminating rapid [[desensitization (medicine)|desensitization]] of the receptor, and potentiating [[glutamate]] currents by as much as 18-fold at the highest concentration tested (100 [[micromolar|μM]]).<ref name="isbn0-8493-8307-2"/><ref name="pmid8103555">{{cite journal | author = Yamada KA, Tang CM | title = Benzothiadiazides inhibit rapid glutamate receptor desensitization and enhance glutamatergic synaptic currents | journal = Journal of Neuroscience | volume = 13 | issue = 9 | pages = 3904–15 |date=September 1993 | pmid = 8103555 | doi = | url = http://www.jneurosci.org/cgi/pmidlookup?view=long&pmid=8103555}}</ref><ref name="pmid7915948">{{cite journal | author = Bertolino M, Baraldi M, Parenti C, ''et al.'' | 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 = 267–78 | year = 1993 | pmid = 7915948 | doi = | url = }}</ref><ref name="isbn3-540-22568-4">{{cite book | author = Ströhle, Andreas; Bilkei-Gorzo, A.; Holsboer, Florian | title = Anxiety and anxiolytic drugs | publisher = Springer | location = Berlin | year = 2005 | pages = 566 | isbn = 3-540-22568-4 | oclc = | doi = | url = http://books.google.com/books?id=RDP4_sBnsl4C&lpg=PA255&dq=Cyclothiazide&pg=PA256#v=onepage&q=Cyclothiazide&f=false
}}</ref> Additionally, in 2003, cyclothiazide was also found to act as a [[GABAA receptor|GABA<sub>A</sub> receptor]] [[negative allosteric modulator]], potently inhibiting GABA<sub>A</sub>-mediated currents.<ref name="pmid14534329">{{cite journal | author = 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 = 13025–9 |date=October 2003 | pmid = 14534329 | pmc = 240738 | doi = 10.1073/pnas.2133370100 | url = http://www.pnas.org/cgi/pmidlookup?view=long&pmid=14534329}}</ref> In animals it is a powerful [[convulsant]], robustly enhancing [[epileptiform]] activity and inducing [[seizure]]s, but without producing any apparent [[neurotoxicity|neuronal death]].<ref name="pmid16423850">{{cite journal | author = 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 = 605–18 |date=March 2006 | pmid = 16423850 | pmc = 1805799 | doi = 10.1113/jphysiol.2005.103812 | url = http://www.jphysiol.org/cgi/pmidlookup?view=long&pmid=16423850}}</ref><ref name="pmid20678492">{{cite journal | author = 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| issue = | pages = 207–213|date=July 2010 | pmid = 20678492 | doi = 10.1016/j.brainres.2010.07.088 | url = http://linkinghub.elsevier.com/retrieve/pii/S0006-8993(10)01678-1 | pmc = 2947190}}</ref>


[[Category:Drugs]]
== References ==
{{Reflist}}


{{WH}}
{{Diuretics}}
{{Symporter inhibitors}}
{{Glutamatergics}}
{{GABAergics}}


{{WS}}
[[Category:Diuretics]]
[[Category:Sulfonamides]]
[[Category:AMPA receptor modulators]]
[[Category:Benzothiadiazines]]
[[Category:Organochlorides]]

Revision as of 01:01, 25 July 2014

Cyclothiazide
Clinical data
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC14H16ClN3O4S2
Molar mass389.88 g/mol
3D model (JSmol)
 ☒N☑Y (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. p. 1932. ISBN 3-88763-075-0.
  2. ↑ Sittig, Marshall (1988). Pharmaceutical manufacturing encyclopedia. Park Ridge, N.J., U.S.A: Noyes Publications. p. 1756. ISBN 0-8155-1144-2.
  3. ↑ 3.0 3.1 Skolnick, Phil; Palfreyman, Michael G.; Reynolds, Ian J. (1994). Direct and allosteric control of glutamate receptors. Boca Raton: CRC Press. p. 174. ISBN 0-8493-8307-2.
  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.
  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. p. 566. ISBN 3-540-22568-4.
  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.
  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.
  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.

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