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.com	International Drug Names
MedlinePlus	a682619
Routes of administration	Oral
ATC code	R06AE04 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 1-[(4-Chlorophenyl)(phenyl)methyl]-4-methylpiperazine
CAS Number	82-93-9^Y
PubChem CID	2710
ChemSpider	2609^Y
UNII	M26C4IP44P
ChEMBL	ChEMBL22150^Y
CompTox Dashboard (EPA)	DTXSID9048011
ECHA InfoCard	100.001.315
Chemical and physical data
Formula	C18H21ClN2
Molar mass	300.83 g·mol^−1
3D model (JSmol)	Interactive image
SMILES Clc1ccc(cc1)C(c2ccccc2)N3CCN(CC3)C
InChI 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^Y Key:WFNAKBGANONZEQ-UHFFFAOYSA-N^Y
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See also

• Cyclizine
• Homochlorcyclizine
• Meclizine

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. David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
3. Hall, Judith A.; Morton, Ian (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 Edition). Elsevier (Educa Books). ISBN 2-84299-899-5.
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): 459–65. PMID 6120505.
6. He, S.; Lin, B.; Chu, V.; Hu, Z.; Hu, X.; Xiao, J.; Wang, A. Q.; Schweitzer, C. J.; Li, Q.; Imamura, M.; Hiraga, N.; Southall, N.; Ferrer, M.; Zheng, W.; Chayama, K.; Marugan, J. J.; Liang, T. J. (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, Ana Maria; Pecheur, Eve-Isabelle; Chen, Zhilei (July 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.
8. Santos, Felipe R. S.; Nunes, Damiana A. F.; Lima, William G.; Davyt, Danilo; Santos, Luciana L.; Taranto, Alex G.; M. S. Ferreira, Jaqueline (2019). "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. ISSN 1549-9596.