Cyclothiazide

	WikiDoc Resources for Cyclothiazide
Articles
Most recent articles on Cyclothiazide Most cited articles on Cyclothiazide Review articles on Cyclothiazide Articles on Cyclothiazide in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Cyclothiazide Images of Cyclothiazide Photos of Cyclothiazide Podcasts & MP3s on Cyclothiazide Videos on Cyclothiazide
Evidence Based Medicine
Cochrane Collaboration on Cyclothiazide Bandolier on Cyclothiazide TRIP on Cyclothiazide
Clinical Trials
Ongoing Trials on Cyclothiazide at Clinical Trials.gov Trial results on Cyclothiazide Clinical Trials on Cyclothiazide at Google
Guidelines / Policies / Govt
US National Guidelines Clearinghouse on Cyclothiazide NICE Guidance on Cyclothiazide NHS PRODIGY Guidance FDA on Cyclothiazide CDC on Cyclothiazide
Books
Books on Cyclothiazide
News
Cyclothiazide in the news Be alerted to news on Cyclothiazide News trends on Cyclothiazide
Commentary
Blogs on Cyclothiazide
Definitions
Definitions of Cyclothiazide
Patient Resources / Community
Patient resources on Cyclothiazide Discussion groups on Cyclothiazide Patient Handouts on Cyclothiazide Directions to Hospitals Treating Cyclothiazide Risk calculators and risk factors for Cyclothiazide
Healthcare Provider Resources
Symptoms of Cyclothiazide Causes & Risk Factors for Cyclothiazide Diagnostic studies for Cyclothiazide Treatment of Cyclothiazide
Continuing Medical Education (CME)
CME Programs on Cyclothiazide
International
Cyclothiazide en Espanol Cyclothiazide en Francais
Business
Cyclothiazide in the Marketplace Patents on Cyclothiazide
Experimental / Informatics
List of terms related to Cyclothiazide

Cyclothiazide
Clinical data
ATC code	C03AA09 (WHO) ;
Legal status
Legal status	In general: ℞ (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 ;
PubChem CID	2910;
DrugBank	DB00606 ;
ChemSpider	4535011 ;
UNII	P71U09G5BW;
KEGG	D01256 ;
ChEMBL	ChEMBL61593 ;
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
Formula	C14H16ClN3O4S2
Molar mass	389.88 g/mol
3D model (JSmol)	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 ; Key:BOCUKUHCLICSIY-QJWLJZLASA-N ;
(what is this?) (verify)

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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 GABA_A receptor negative allosteric modulator, potently inhibiting GABA_A-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

↑ 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, Marshall (1988). Pharmaceutical manufacturing encyclopedia. Park Ridge, N.J., U.S.A: Noyes Publications. p. 1756. ISBN 0-8155-1144-2.
↑ ^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.
↑ 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.
↑ 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.
↑ Ströhle, Andreas; Bilkei-Gorzo, A.; Holsboer, Florian (2005). Anxiety and anxiolytic drugs. Berlin: Springer. p. 566. ISBN 3-540-22568-4.
↑ 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.
↑ 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.
↑ 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.

[isbn3-88763-075-0-1] 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.

[isbn0-8155-1144-2-2] Sittig, Marshall (1988). Pharmaceutical manufacturing encyclopedia. Park Ridge, N.J., U.S.A: Noyes Publications. p. 1756. ISBN 0-8155-1144-2.

[isbn0-8493-8307-2-3] 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.

[pmid8103555-4] 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.

[pmid7915948-5] 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.

[isbn3-540-22568-4-6] Ströhle, Andreas; Bilkei-Gorzo, A.; Holsboer, Florian (2005). Anxiety and anxiolytic drugs. Berlin: Springer. p. 566. ISBN 3-540-22568-4.

[pmid14534329-7] 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.

[pmid16423850-8] 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.

[pmid20678492-9] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

Clinical data

ATC code	C03AA09 (WHO)
Legal status
Legal status	In general: ℞ (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
DrugBank	DB00606^N
ChemSpider	4535011^N
UNII	P71U09G5BW
KEGG	D01256^Y
ChEMBL	ChEMBL61593^N
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
Formula	C₁₄H₁₆ClN₃O₄S₂
Molar mass	389.88 g/mol
3D model (JSmol)	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

Overview

References

Navigation menu