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
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
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 |
|||
Target ID: CHEMBL379 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26599718 |
0.044 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AHIST Approved UseUses
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 Date1.35820804E12 |
Cmax
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: 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%) Sources: Page: Supplemental Table 3 p.9Dry mouth Headaches (17%) Lightheadedness (17%) Nervousness (17%) Concentration impaired (17%) Numbness (25%) Fatigue (17%) Urination difficulty (8%) |
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 Health Status: unhealthy Condition: Respiratory allergies Sources: |
Other AEs: Drowsiness, Excitability... Other AEs: Drowsiness Sources: Excitability |
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: 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 Health Status: unhealthy Condition: Respiratory allergies Sources: |
|
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 Health Status: unhealthy Condition: Respiratory allergies Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/5265/ |
yes | |||
Page: 60.0 |
yes | |||
Page: 60.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
PHYSIOLOGICAL DISTRIBUTION AND METABOLIC INACTIVATION OF CHLORCYCLIZINE AND CYCLIZINE. | 1965 Jul |
|
Experimental myopathy induced by amphiphilic cationic compounds including several psychotropic drugs. | 1979 |
|
Quantitative enantiomeric analysis of chlorcyclizine, hydroxyzine, and meclizine by capillary electrophoresis. | 2003 Jul |
|
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. | 2005 Feb |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7683592
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
Edited
Fri Dec 15 18:50:29 UTC 2023
by
admin
on
Fri Dec 15 18:50:29 UTC 2023
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Record UNII |
61Y56T95YL
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Record Status |
Validated (UNII)
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Record Version |
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |