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

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
Structure of CHLORCYCLIZINE

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

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

2013
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
Screening for anti-HIV drugs that can combine virucidal and virustatic activities synergistically.
2000 Apr
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
Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography.
2006 Feb 13
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.
2007 Apr 20
Chlorpromazine and chlorcyclizine in the prevention of postoperative nausea and vomiting. Acta Anaesth. Scandinav. 1958, 2, 153-162.
2007 Sep
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 Fri Dec 15 19:07:00 GMT 2023
Edited
by admin
on Fri Dec 15 19:07:00 GMT 2023
Record UNII
M26C4IP44P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORCYCLIZINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
chlorcyclizine [INN]
Common Name English
CHLORCYCLIZINE [HSDB]
Common Name English
ALERGICIDE
Brand Name English
PIPERAZINE, 1-((4-CHLOROPHENYL)PHENYLMETHYL)-4-METHYL-
Systematic Name English
Chlorcyclizine [WHO-DD]
Common Name English
NSC-25246
Code English
COMPD 47-282
Code English
1-(P-CHLORO-.ALPHA.-PHENYLBENZYL)-4-METHYLPIPERAZINE
Common Name English
PERAZYL
Brand Name English
CHLORCYCLIZINE [MI]
Common Name English
TRIHISTAN
Brand Name English
CHLORCYCLIZINE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
WHO-VATC QR06AE04
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
LIVERTOX 191
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
WHO-ATC R06AE04
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
Code System Code Type Description
NSC
25246
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
SMS_ID
100000081560
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
DRUG CENTRAL
593
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
MESH
C084597
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
WIKIPEDIA
CHLORCYCLIZINE
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
HSDB
3217
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
RXCUI
2354
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY RxNorm
PUBCHEM
2710
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
INN
1301
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
ChEMBL
CHEMBL22150
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
NCI_THESAURUS
C81138
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
DRUG BANK
DB08936
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
FDA UNII
M26C4IP44P
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
CAS
82-93-9
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
EVMPD
SUB06178MIG
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID9048011
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
DAILYMED
M26C4IP44P
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-446-0
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY
MERCK INDEX
m3352
Created by admin on Fri Dec 15 19:07:00 GMT 2023 , Edited by admin on Fri Dec 15 19:07:00 GMT 2023
PRIMARY Merck Index
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
ENANTIOMER -> RACEMATE
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC