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Details

Stereochemistry RACEMIC
Molecular Formula C18H21ClN2.ClH
Molecular Weight 337.287
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORCYCLIZINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=MSIJLVMSKDXAQN-UHFFFAOYSA-N
InChI=1S/C18H21ClN2.ClH/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;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

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

CNS Active
3913
Curator's Comment: Chlorcyclizine is known to cross the blood-brain barrier and cause side effects such as sedation

Originator

Approval Year

1949
70
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Inhibitor
8297
 0.044 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30711416/
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d50b5154-20a3-4c5b-ad7b-08c081340b12&type=display
unhealthy
Health Status: unhealthy
Condition: Respiratory allergies
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d50b5154-20a3-4c5b-ad7b-08c081340b12&type=display
Other AEs: Drowsiness, Excitability...
Other AEs:
Drowsiness
Excitability
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d50b5154-20a3-4c5b-ad7b-08c081340b12&type=display
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://pubmed.ncbi.nlm.nih.gov/30711416
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:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d50b5154-20a3-4c5b-ad7b-08c081340b12&type=display
unhealthy
Health Status: unhealthy
Condition: Respiratory allergies
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d50b5154-20a3-4c5b-ad7b-08c081340b12&type=display
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:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d50b5154-20a3-4c5b-ad7b-08c081340b12&type=display
unhealthy
Health Status: unhealthy
Condition: Respiratory allergies
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d50b5154-20a3-4c5b-ad7b-08c081340b12&type=display
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
270

P-gp
1537

MRP1
107
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 yes
MRP1
107
 yes
P-gp
1537
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
Hairui
HR144783
http://www.hairuichem.com/en/product/82-93-9.html
Molcore
MC573099
https://www.molcore.com/product/82-93-9
Sigma-Aldrich
SML1473_SIGMA
https://www.sigmaaldrich.com/catalog/product/sigma/sml1473?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule
S523476
http://www.smolecule.com/products/s523476
THE BioTek
bt-264138
https://www.thebiotek.com/product/inhibitors/bt-264138
THE BioTek
bt-295533
https://www.thebiotek.com/product/others/bt-295533
iChemical
EBD1758
http://www.ichemical.com/chemicals/cas-82-93-9
mcule
MCULE-4720374498
https://mcule.com/MCULE-4720374498/
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

Patents

20020028243
14
20020064547
6

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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:15:36 GMT 2023
Edited
by admin
on Fri Dec 15 19:15:36 GMT 2023
Record UNII
NPB7A7874U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORCYCLIZINE HYDROCHLORIDE
EP   MART.   MI   VANDF   WHO-DD  
Common Name English
CHLORCYCLIZINE HYDROCHLORIDE [VANDF]
Common Name English
CHLORCYCLIZINE HCL
Common Name English
NSC-169496
Code English
PERAZIL
Brand Name English
1-(P-CHLORO-.ALPHA.-PHENYLBENZYL)-4-METHYLPIPERAZINE MONOHYDROCHLORIDE
Common Name English
CHLORCYCLIZINIUM CHLORIDE
Common Name English
CHLORCYCLIZINE MONOHYDROCHLORIDE
Common Name English
CHLORCYCLIZINE HYDROCHLORIDE [MART.]
Common Name English
CHLORCYCLIZINE HYDROCHLORIDE [MI]
Common Name English
HISTANTIN
Brand Name English
PIPERAZINE, 1-((4-CHLOROPHENYL)PHENYLMETHYL)-4-METHYL-, MONOHYDROCHLORIDE
Common Name English
AH-289
Code English
1-(P-CHLOROBENZHYDRYL)-4-METHYLPIPERAZINE MONOHYDROCHLORIDE
Common Name English
DI-PARALENE
Brand Name English
CHLORCYCLIZINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
Chlorcyclizine hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 341.12
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
Code System Code Type Description
FDA UNII
NPB7A7874U
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID7045360
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
ChEMBL
CHEMBL22150
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
CAS
14362-31-3
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
DRUG BANK
DBSALT001022
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
EVMPD
SUB01212MIG
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
PUBCHEM
62413
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
DAILYMED
NPB7A7874U
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
NSC
169496
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
ECHA (EC/EINECS)
238-335-1
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
CAS
1620-21-9
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
NON-SPECIFIC STOICHIOMETRY
NCI_THESAURUS
C76669
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
MERCK INDEX
m3352
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY Merck Index
SMS_ID
100000092802
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY
RXCUI
235725
Created by admin on Fri Dec 15 19:15:37 GMT 2023 , Edited by admin on Fri Dec 15 19:15:37 GMT 2023
PRIMARY RxNorm
Related Record Type Details
Structure of CHLORCYCLIZINE
PARENT -> SALT/SOLVATE
Structure of CHLORCYCLIZINE HYDROCHLORIDE, (R)-
ENANTIOMER -> RACEMATE
Structure of CHLORCYCLIZINE HYDROCHLORIDE, (S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of CHLORCYCLIZINE
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