Chlorcyclizine

Chlorcyclizine (Di-Paralene, Mantadil, Pruresidine, Trihistan) is a first-generation antihistamine of the diphenylmethylpiperazine group marketed in the United States and certain other countries.[1][2][3] It is used primarily to treat allergy symptoms such as rhinitis, urticaria, and pruritus, and may also be used as an antiemetic.[1][2][3] In addition to its antihistamine effects, chlorcyclizine also has some anticholinergic, antiserotonergic, and local anesthetic properties.[4][5] It also has been studied as a potential treatment for various flaviviruses like Hepatitis C and Zika Virus.[6][7][8]

Chlorcyclizine
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa682619
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 1-[(4-Chlorophenyl)(phenyl)methyl]-4-methylpiperazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.315
Chemical and physical data
FormulaC18H21ClN2
Molar mass300.83 g·mol−1
3D model (JSmol)
  • Clc1ccc(cc1)C(c2ccccc2)N3CCN(CC3)C
  • InChI=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 checkY
  • Key:WFNAKBGANONZEQ-UHFFFAOYSA-N checkY
  (verify)

See also

References
  1. Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.
  2. Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
  3. Hall JA, Morton I (1999). Concise dictionary of pharmacological agents: properties and synonyms. Kluwer Academic. ISBN 0-7514-0499-3.
  4. Dorland Staff (2008). Dorland Dictionnaire Medical Bilingue Francais-anglais / Anglais-francais: + E-book a Telecharger (French ed.). Elsevier (Educa Books). ISBN 978-2-84299-899-8.
  5. Rogóz Z, Skuza G, Sowińska H (November 1981). "The effect of the antihistaminic drugs on the central action of 5-hydroxytryptophan in mice". Polish Journal of Pharmacology and Pharmacy. 33 (4): 459–465. PMID 6120505.
  6. He S, Lin B, Chu V, Hu Z, Hu X, Xiao J, et al. (April 2015). "Repurposing of the antihistamine chlorcyclizine and related compounds for treatment of hepatitis C virus infection". Science Translational Medicine. 7 (282): 282ra49. doi:10.1126/scitranslmed.3010286. PMC 6420960. PMID 25855495.
  7. Chamoun-Emanuelli AM, Pécheur EI, Chen Z (September 2014). "Benzhydrylpiperazine compounds inhibit cholesterol-dependent cellular entry of hepatitis C virus". Antiviral Research. 109: 141–148. doi:10.1016/j.antiviral.2014.06.014. PMID 25019406.
  8. Santos FR, Nunes DA, Lima WG, Davyt D, Santos LL, Taranto AG, Ferreira JM (February 2020). "Identification of Zika Virus NS2B-NS3 Protease Inhibitors by Structure-Based Virtual Screening and Drug Repurposing Approaches". Journal of Chemical Information and Modeling. 60 (2): 731–737. doi:10.1021/acs.jcim.9b00933. PMID 31850756. S2CID 209409716.
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