CHLORCYCLIZINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H21ClN2
Molecular Weight	300.826
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(Cl)C=C3

InChI

InChIKey=WFNAKBGANONZEQ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C18H21ClN2
Molecular Weight	300.826
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

Chlorcyclizine is a first generation phenylpiperazine class antihistamine used to treat urticaria, rhinitis, pruritus, and other allergy symptoms. Chlorcyclizine also has some local anesthetic, anticholinergic, and antiserotonergic properties, and can be used as an antiemetic. Chlorcyclizine temporarily relieves the symptoms due to hay fever or other upper respiratory allergies. It has also being shown to possess in vitro and in vivo activity against hepatitis C virus.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315	Antagonist 2,778
Hepatitis C virus 22	Inhibitor 8,297		0.044 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 100	Primary		Approved 8,429	AHIST

C_max

C_max

Value	Dose	Co-administered	Analyte	Population
79.71 ng/mL	75 mg single, oral		CHLORCYCLIZINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
75 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 54–61 n = 12	Other AEs: Drowsiness, Dry mouth...
25 mg 3 times / day multiple, oral Recommended	unhealthy	Other AEs: Drowsiness, Excitability...

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AEs

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AE	Significance	Dose	Population
Dry mouth		75 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 54–61 n = 12
Concentration impaired	17%	75 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 54–61 n = 12
Fatigue	17%	75 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 54–61 n = 12
Headaches	17%	75 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 54–61 n = 12
Lightheadedness	17%	75 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 54–61 n = 12

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 270 P-gp 1,537 MRP1 107

Drug as victim

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Target	Modality	Activity
CYP 270	substrate 3,367	yes
MRP1 107	substrate 3,367	yes
P-gp 1,537	substrate 3,367	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	DY573099	https://www.001chemical.com/chem/82-93-9
Alfa Chemistry	AP82939	https://reagents.alfa-chemistry.com/product/chlorcyclizine-cas-82-93-9-17031.html
BLD Pharm	BD120656	http://www.bldpharm.com/products/82-93-9.html
ChemMol	30105016	http://www.chemmol.com/chemmol/30105016.html
ChemMol	99160492	http://www.chemmol.com/chemmol/99160492.html

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PubMed

Show entries

Title	Date	PubMed
Pruritogenic activity of prostaglandin E2.	1977	74166
Experimental myopathy induced by amphiphilic cationic compounds including several psychotropic drugs.	1979	34807
Biotransformation of cyclizine in greyhounds. 1: Identification and analysis of cyclizine and some basic metabolites in canine urine by gas chromatography-mass spectrometry.	2002 Sep	12396276
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system.	2005 Feb	15342952
Pronounced inhibitory effect of chlorcyclizine (CCZ) in experimental hepatocarcinoma.	2006 Jan-Feb	16433035

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Patents

Sample Use Guides

In Vivo Use Guide

1 tablet by mouth every 6-8 hours, not to exceed 3 tablets in 24 hours, or as directed by a doctor

Route of Administration: Oral

In Vitro Use Guide

Plocamadiene A (1 ug/mL)- produced slow onset, sustained contraction of the guinea-pig isolated ileum (GPI), was significantly reduced by H1-histamine receptor antagonist chlorcyclizine (10 nmol/L).