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Updating {{drugbox}} (changes to verified fields - updated 'KEGG_Ref') per Chem/Drugbox validation (report errors or bugs)
 
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{{Short description|Chemical compound}}
{{drugbox
{{Drugbox
| Verifiedfields = changed
| UNII_Ref = {{fdacite|changed|FDA}}
| Watchedfields = changed
| verifiedrevid = 437187307
| IUPAC_name = 1-[(4-Chlorophenyl)(phenyl)methyl]-4-methylpiperazine
| image = Chlorcyclizine.png

<!--Clinical data-->
| tradename =
| Drugs.com = {{drugs.com|international|chlorcyclizine}}
| MedlinePlus = a682619
| pregnancy_category =
| legal_status = Rx-only
| routes_of_administration = Oral
<!--Pharmacokinetic data-->
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 82-93-9
| ATC_prefix = R06
| ATC_suffix = AE04
| PubChem = 2710
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2609
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M26C4IP44P
| UNII = M26C4IP44P
| verifiedrevid = 414062299
| IUPAC_name = 1-[(4-chlorophenyl)(phenyl)methyl]-4-methylpiperazine
| image = Chlorcyclizine.png
| InChI = 1/C18H21ClN2/c1-20-11-13-21(14-12-20)18(15-5-3-2-4-6-15)16-7-9-17(19)10-8-16/h2-10,18H,11-14H2,1H3
| InChIKey = WFNAKBGANONZEQ-UHFFFAOYAF
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 22150
| ChEMBL = 22150

<!--Chemical data-->
| C=18 | H=21 | Cl=1 | N=2
| smiles = Clc1ccc(cc1)C(c2ccccc2)N3CCN(CC3)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H21ClN2/c1-20-11-13-21(14-12-20)18(15-5-3-2-4-6-15)16-7-9-17(19)10-8-16/h2-10,18H,11-14H2,1H3
| StdInChI = 1S/C18H21ClN2/c1-20-11-13-21(14-12-20)18(15-5-3-2-4-6-15)16-7-9-17(19)10-8-16/h2-10,18H,11-14H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WFNAKBGANONZEQ-UHFFFAOYSA-N
| StdInChIKey = WFNAKBGANONZEQ-UHFFFAOYSA-N
| CAS_number = 82-93-9
| ATC_prefix = R06
| ATC_suffix = AE04
| PubChem = 2710
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2609
| C = 18 | H = 21 | Cl = 1 | N = 2
| molecular_weight = 300.826 g/mol
| smiles = Clc1ccc(cc1)C(c2ccccc2)N3CCN(CC3)C
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_category =
| legal_status = Rx-only
| routes_of_administration = Oral
}}
}}


'''Chlorcyclizine''' ('''Di-Paralene''', '''Mantadil''', '''Pruresidine''', '''Trihistan''') is a [[first-generation antihistamine]] of the [[phenylpiperazine]] class marketed in the [[United States]] and certain other countries.<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 = | isbn = 3-88763-075-0 | oclc = | doi = | url = http://books.google.com/books?id=5GpcTQD_L2oC&lpg=PA1228&dq=Chlorcyclizine&pg=PA212#v=onepage&q&f=false}}</ref><ref name="isbn0-412-46630-9">{{cite book | author = David J. Triggle | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | pages = | isbn = 0-412-46630-9 | oclc = | doi = | url = http://books.google.com/books?id=DeX7jgInYFMC&lpg=PA417&dq=Chlorcyclizine&pg=PA417#v=onepage&q&f=false}}</ref><ref name="isbn0-7514-0499-3">{{cite book | author = Hall, Judith A.; Morton, Ian | title = Concise dictionary of pharmacological agents: properties and synonyms | publisher = Kluwer Academic | location = | year = 1999 | pages = | isbn = 0-7514-0499-3 | oclc = | doi = | url = http://books.google.com/books?id=mqaOMOtk61IC&lpg=PA72&dq=Chlorcyclizine&pg=PA72#v=onepage&q&f=false}}</ref> It is used primarily to treat [[allergy]] [[symptom]]s such as [[rhinitis]], [[urticaria]], and [[pruritus]], and may also be used as an [[antiemetic]].<ref name="isbn3-88763-075-0"/><ref name="isbn0-412-46630-9"/><ref name="isbn0-7514-0499-3"/> In addition to its [[antihistamine]] effects, chlorcyclizine also has some [[anticholinergic]], [[antiserotonergic]], and [[local anesthetic]] properties.<ref name="isbn2-84299-899-5">{{cite book | author = Dorland Staff | title = Dorland Dictionnaire Medical Bilingue Francais-anglais / Anglais-francais: + E-book a Telecharger (French Edition) | publisher = Elsevier (Educa Books) | location = | year = 2008 | pages = | isbn = 2-84299-899-5 | oclc = | doi = | url = http://books.google.com/books?id=tQNqwsnkK-QC&lpg=PA1152&dq=chlorcyclizine%20anticholinergic&lr&as_brr=3&pg=PA1152#v=onepage&q&f=false}}</ref><ref name="pmid6120505">{{cite journal | author = Rogóz Z, Skuza G, Sowińska H | title = The effect of the antihistaminic drugs on the central action of 5-hydroxytryptophan in mice | journal = Polish Journal of Pharmacology and Pharmacy | volume = 33 | issue = 4 | pages = 459–65 | year = 1981 | month = November | pmid = 6120505 | doi = | url = }}</ref>
'''Chlorcyclizine''' ('''Di-Paralene''', '''Mantadil''', '''Pruresidine''', '''Trihistan''') is a [[first-generation antihistamine]] of the [[diphenylmethylpiperazine]] group marketed in the [[United States]] and certain other countries.<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 | isbn = 3-88763-075-0 | url = https://books.google.com/books?id=5GpcTQD_L2oC&q=Chlorcyclizine&pg=PA212}}</ref><ref name="isbn0-412-46630-9">{{cite book | vauthors = Triggle DJ | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | isbn = 0-412-46630-9 | url = https://books.google.com/books?id=DeX7jgInYFMC&q=Chlorcyclizine&pg=PA417}}</ref><ref name="isbn0-7514-0499-3">{{cite book | vauthors = Hall JA, Morton I | title = Concise dictionary of pharmacological agents: properties and synonyms | publisher = Kluwer Academic | year = 1999 | isbn = 0-7514-0499-3 | url = https://books.google.com/books?id=mqaOMOtk61IC&q=Chlorcyclizine&pg=PA72}}</ref> It is used primarily to treat [[allergy]] [[symptom]]s such as [[rhinitis]], [[urticaria]], and [[pruritus]], and may also be used as an [[antiemetic]].<ref name="isbn3-88763-075-0"/><ref name="isbn0-412-46630-9"/><ref name="isbn0-7514-0499-3"/> In addition to its [[antihistamine]] effects, chlorcyclizine has some [[anticholinergic]], [[antiserotonergic]], and [[local anesthetic]] properties.<ref name="isbn2-84299-899-5">{{cite book | author = Dorland Staff | title = Dorland Dictionnaire Medical Bilingue Francais-anglais / Anglais-francais: + E-book a Telecharger | publisher = Elsevier (Educa Books) | year = 2008 | isbn = 978-2-84299-899-8 | url = https://books.google.com/books?id=tQNqwsnkK-QC&q=chlorcyclizine%20anticholinergic&pg=PA1152| edition = French }}</ref><ref name="pmid6120505">{{cite journal | vauthors = Rogóz Z, Skuza G, Sowińska H | title = The effect of the antihistaminic drugs on the central action of 5-hydroxytryptophan in mice | journal = Polish Journal of Pharmacology and Pharmacy | volume = 33 | issue = 4 | pages = 459–465 | date = November 1981 | pmid = 6120505 }}</ref> It has been studied as a potential treatment for various [[flavivirus]]es like [[hepatitis C]] and [[Zika virus]].<ref>{{cite journal | vauthors = He S, Lin B, Chu V, Hu Z, Hu X, Xiao J, Wang AQ, Schweitzer CJ, Li Q, Imamura M, Hiraga N, Southall N, Ferrer M, Zheng W, Chayama K, Marugan JJ, Liang TJ | display-authors = 6 | title = Repurposing of the antihistamine chlorcyclizine and related compounds for treatment of hepatitis C virus infection | journal = Science Translational Medicine | volume = 7 | issue = 282 | pages = 282ra49 | date = April 2015 | pmid = 25855495 | pmc = 6420960 | doi = 10.1126/scitranslmed.3010286 }}</ref><ref>{{cite journal | vauthors = Chamoun-Emanuelli AM, Pécheur EI, Chen Z | title = Benzhydrylpiperazine compounds inhibit cholesterol-dependent cellular entry of hepatitis C virus | journal = Antiviral Research | volume = 109 | pages = 141–148 | date = September 2014 | pmid = 25019406 | doi = 10.1016/j.antiviral.2014.06.014 }}</ref><ref name="SantosNunes2019">{{cite journal | vauthors = Santos FR, Nunes DA, Lima WG, Davyt D, Santos LL, Taranto AG, Ferreira JM | title = Identification of Zika Virus NS2B-NS3 Protease Inhibitors by Structure-Based Virtual Screening and Drug Repurposing Approaches | journal = Journal of Chemical Information and Modeling | volume = 60 | issue = 2 | pages = 731–737 | date = February 2020 | pmid = 31850756 | doi = 10.1021/acs.jcim.9b00933 | s2cid = 209409716 }}</ref>


== See also ==
== See also ==
* [[Cyclizine]]
* [[Cyclizine]]
* [[Homochlorcyclizine]]
* [[Homochlorcyclizine]]
* [[Meclozine]]
* [[Meclizine]]


==References==
== References ==
{{Reflist}}
{{Reflist}}


{{Antihistamines}}
{{Analgesics}}
{{Antiemetics}}
{{Antiemetics}}
{{Analgesics}}
{{Antihistamines}}

{{Cholinergics}}
{{Cholinergics}}
{{Histaminergics}}
{{Histaminergics}}
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[[Category:H1 receptor antagonists]]
[[Category:H1 receptor antagonists]]
[[Category:Organochlorides]]
[[Category:Chlorcyclizines| ]]
[[Category:Piperazines]]
[[Category:4-Methylpiperazin-1-yl compounds]]


{{respiratory-system-drug-stub}}
[[it:Clorciclizina]]
[[th:คลอร์ไซคลิซีน]]