U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H21ClN2.2ClH
Molecular Weight 373.748
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORCYCLIZINE DIHYDROCHLORIDE

SMILES

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

InChI

InChIKey=FLEBQACKYGHXTR-UHFFFAOYSA-N
InChI=1S/C18H21ClN2.2ClH/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;2*1H

HIDE SMILES / InChI

Molecular Formula C18H21ClN2
Molecular Weight 300.826
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment: Chlorcyclizine is known to cross the blood-brain barrier and cause side effects such as sedation

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AHIST

Approved Use

Uses temporarily relieves these symptoms due to hay fever or other upper respiratory allergies: runny nose sneezing itching of the nose or throat itchy, watery eyes

Launch Date

1.35820804E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
79.71 ng/mL
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORCYCLIZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources: Page: Supplemental Table 3 p.9
unhealthy, 54–61
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis C
Age Group: 54–61
Sex: M+F
Population Size: 12
Sources: Page: Supplemental Table 3 p.9
Other AEs: Drowsiness, Dry mouth...
Other AEs:
Drowsiness (42%)
Dry mouth
Headaches (17%)
Lightheadedness (17%)
Nervousness (17%)
Concentration impaired (17%)
Numbness (25%)
Fatigue (17%)
Urination difficulty (8%)
Sources: Page: Supplemental Table 3 p.9
25 mg 3 times / day multiple, oral
Recommended
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Sources:
unhealthy
Other AEs: Drowsiness, Excitability...
AEs

AEs

AESignificanceDosePopulation
Dry mouth
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources: Page: Supplemental Table 3 p.9
unhealthy, 54–61
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis C
Age Group: 54–61
Sex: M+F
Population Size: 12
Sources: Page: Supplemental Table 3 p.9
Concentration impaired 17%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources: Page: Supplemental Table 3 p.9
unhealthy, 54–61
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis C
Age Group: 54–61
Sex: M+F
Population Size: 12
Sources: Page: Supplemental Table 3 p.9
Fatigue 17%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources: Page: Supplemental Table 3 p.9
unhealthy, 54–61
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis C
Age Group: 54–61
Sex: M+F
Population Size: 12
Sources: Page: Supplemental Table 3 p.9
Headaches 17%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources: Page: Supplemental Table 3 p.9
unhealthy, 54–61
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis C
Age Group: 54–61
Sex: M+F
Population Size: 12
Sources: Page: Supplemental Table 3 p.9
Lightheadedness 17%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources: Page: Supplemental Table 3 p.9
unhealthy, 54–61
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis C
Age Group: 54–61
Sex: M+F
Population Size: 12
Sources: Page: Supplemental Table 3 p.9
Nervousness 17%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources: Page: Supplemental Table 3 p.9
unhealthy, 54–61
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis C
Age Group: 54–61
Sex: M+F
Population Size: 12
Sources: Page: Supplemental Table 3 p.9
Numbness 25%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources: Page: Supplemental Table 3 p.9
unhealthy, 54–61
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis C
Age Group: 54–61
Sex: M+F
Population Size: 12
Sources: Page: Supplemental Table 3 p.9
Drowsiness 42%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources: Page: Supplemental Table 3 p.9
unhealthy, 54–61
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis C
Age Group: 54–61
Sex: M+F
Population Size: 12
Sources: Page: Supplemental Table 3 p.9
Urination difficulty 8%
75 mg 2 times / day multiple, oral
Highest studied dose
Dose: 75 mg, 2 times / day
Route: oral
Route: multiple
Dose: 75 mg, 2 times / day
Sources: Page: Supplemental Table 3 p.9
unhealthy, 54–61
n = 12
Health Status: unhealthy
Condition: Chronic hepatitis C
Age Group: 54–61
Sex: M+F
Population Size: 12
Sources: Page: Supplemental Table 3 p.9
Drowsiness
25 mg 3 times / day multiple, oral
Recommended
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Sources:
unhealthy
Excitability
25 mg 3 times / day multiple, oral
Recommended
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim
PubMed

PubMed

TitleDatePubMed
PHYSIOLOGICAL DISTRIBUTION AND METABOLIC INACTIVATION OF CHLORCYCLIZINE AND CYCLIZINE.
1965 Jul
Pruritogenic activity of prostaglandin E2.
1977
Experimental myopathy induced by amphiphilic cationic compounds including several psychotropic drugs.
1979
Screening for anti-HIV drugs that can combine virucidal and virustatic activities synergistically.
2000 Apr
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
Quantitative enantiomeric analysis of chlorcyclizine, hydroxyzine, and meclizine by capillary electrophoresis.
2003 Jul
A capillary zone electrophoresis (CZE) method for the determination of cyclizine hydrochloride in tablets and suppositories.
2004 Apr 1
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system.
2005 Feb
Carrier mediated transport of chlorpheniramine and chlorcyclizine across bovine olfactory mucosa: implications on nose-to-brain transport.
2005 Mar
Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography.
2006 Feb 13
Pronounced inhibitory effect of chlorcyclizine (CCZ) in experimental hepatocarcinoma.
2006 Jan-Feb
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.
2007 Apr 20
Enantiomeric quality control of antihistamines in pharmaceuticals by affinity electrokinetic chromatography with human serum albumin as chiral selector.
2007 Jun 5
Chlorpromazine and chlorcyclizine in the prevention of postoperative nausea and vomiting. Acta Anaesth. Scandinav. 1958, 2, 153-162.
2007 Sep
Effects of the histamine H1 antagonist chlorcyclizine on rat fetal palate development.
2010 Dec
Patents

Sample Use Guides

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).
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:01:13 UTC 2023
Edited
by admin
on Thu Jul 06 02:01:13 UTC 2023
Record UNII
61Y56T95YL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORCYCLIZINE DIHYDROCHLORIDE
MI  
Common Name English
CHLORCYCLIZINE DIHYDROCHLORIDE [MI]
Common Name English
PIPERAZINE, 1-(P-CHLORO-.ALPHA.-PHENYLBENZYL)-4-METHYL-, DIHYDROCHLORIDE
Common Name English
PIPERAZINE, 1-((4-CHLOROPHENYL)PHENYLMETHYL)-4-METHYL-, HYDROCHLORIDE (1:2)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID40926270
Created by admin on Thu Jul 06 02:01:13 UTC 2023 , Edited by admin on Thu Jul 06 02:01:13 UTC 2023
PRIMARY
PUBCHEM
101605
Created by admin on Thu Jul 06 02:01:13 UTC 2023 , Edited by admin on Thu Jul 06 02:01:13 UTC 2023
PRIMARY
CAS
129-71-5
Created by admin on Thu Jul 06 02:01:13 UTC 2023 , Edited by admin on Thu Jul 06 02:01:13 UTC 2023
PRIMARY
MERCK INDEX
M3352
Created by admin on Thu Jul 06 02:01:13 UTC 2023 , Edited by admin on Thu Jul 06 02:01:13 UTC 2023
PRIMARY Merck Index
FDA UNII
61Y56T95YL
Created by admin on Thu Jul 06 02:01:13 UTC 2023 , Edited by admin on Thu Jul 06 02:01:13 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE