CHLORCYCLIZINE PAMOATE

US Approved OTC

First approved in 1949

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H16O6.C18H21ClN2
Molecular Weight	689.195
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(Cl)C=C3.OC(=O)C4=CC5=C(C=CC=C5)C(CC6=C7C=CC=CC7=CC(C(O)=O)=C6O)=C4O

InChI

InChIKey=WUJMCJWDNKVBOU-UHFFFAOYSA-N

InChI=1S/C23H16O6.C18H21ClN2/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29;1-20-11-13-21(14-12-20)18(15-5-3-2-4-6-15)16-7-9-17(19)10-8-16/h1-10,24-25H,11H2,(H,26,27)(H,28,29);2-10,18H,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	( + / - )

Molecular Formula	C23H16O6
Molecular Weight	388.3695
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d50b5154-20a3-4c5b-ad7b-08c081340b12&type=display | http://www.pharmaceutical-journal.com/news-and-analysis/antihistamine-could-be-used-as-a-cheaper-hepatitis-c-therapy-study-suggests/20068312.article

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 Target ID: CHEMBL231 Sources: https://www.drugbank.ca/drugs/DB08936 \| https://www.ncbi.nlm.nih.gov/pubmed/21058326	Antagonist 2778
Hepatitis C virus 22 Target ID: CHEMBL379 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26599718	Inhibitor 8297		0.044 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 100 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d50b5154-20a3-4c5b-ad7b-08c081340b12&type=display	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 1.35820804E12

C_max

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 270 P-gp 1537 MRP1 107

Drug as victim

Target	Modality	Activity
CYP 270	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/5265/	yes
MRP1 107	substrate 3367 Sources: https://ir.uiowa.edu/cgi/viewcontent.cgi?article=7864&context=etd#page=60 Page: 60.0	yes
P-gp 1537	substrate 3367 Sources: https://ir.uiowa.edu/cgi/viewcontent.cgi?article=7864&context=etd#page=60 Page: 60.0	yes

Sourcing

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
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

Title	Date	PubMed
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis.	2007 Apr 20	17339039

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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:15:34 UTC 2023` Edited by `admin` on `Fri Dec 15 19:15:34 UTC 2023`
Record UNII	73R47NSS6P
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CHLORCYCLIZINE PAMOATE

Common Name

English

CHLORCYCLIZINE EMBONATE

Common Name

English

2-NAPHTHALENECARBOXYLIC ACID, 4,4'-METHYLENEBIS 3-HYDROXY-, COMPD. WITH 1-((4-CHLOROPHENYL)PHENYLMETHYL)-4-METHYLPIPERAZINE

Common Name

English

Code System Code Type Description

PUBCHEM

24296

Created by admin on Fri Dec 15 19:15:34 UTC 2023 , Edited by admin on Fri Dec 15 19:15:34 UTC 2023

PRIMARY

CAS

10450-53-0

Created by admin on Fri Dec 15 19:15:34 UTC 2023 , Edited by admin on Fri Dec 15 19:15:34 UTC 2023

PRIMARY

FDA UNII

73R47NSS6P

Created by admin on Fri Dec 15 19:15:34 UTC 2023 , Edited by admin on Fri Dec 15 19:15:34 UTC 2023

PRIMARY

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ENANTIOMER -> RACEMATE


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CHLORCYCLIZINE

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d50b5154-20a3-4c5b-ad7b-08c081340b12&type=display | http://www.pharmaceutical-journal.com/news-and-analysis/antihistamine-could-be-used-as-a-cheaper-hepatitis-c-therapy-study-suggests/20068312.article

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

Doses

AEs

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=d50b5154-20a3-4c5b-ad7b-08c081340b12&type=display | http://www.pharmaceutical-journal.com/news-and-analysis/antihistamine-could-be-used-as-a-cheaper-hepatitis-c-therapy-study-suggests/20068312.article

C_max