Details
Stereochemistry | RACEMIC |
Molecular Formula | C25H27ClN2 |
Molecular Weight | 390.9491 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cc1cccc(c1)CN2CCN(CC2)C(c3ccccc3)c4ccc(cc4)Cl
InChI
InChIKey=OCJYIGYOJCODJL-UHFFFAOYSA-N
InChI=1S/C25H27ClN2/c1-20-6-5-7-21(18-20)19-27-14-16-28(17-15-27)25(22-8-3-2-4-9-22)23-10-12-24(26)13-11-23/h2-13,18,25H,14-17,19H2,1H3
Molecular Formula | C25H27ClN2 |
Molecular Weight | 390.9491 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB00737Curator's Comment:: Description was created based on several sources, including
https://www.drugs.com/meclizine.html
Sources: http://www.drugbank.ca/drugs/DB00737
Curator's Comment:: Description was created based on several sources, including
https://www.drugs.com/meclizine.html
Meclizine, a piperazine-derivative H1-receptor antagonist similar to buclizine, cyclizine, and hydroxyzine, is used as an antivertigo/antiemetic agent. Meclizine is used in the management of nausea, vomiting, and dizziness associated with motion sickness and vertigo in diseases affecting the vestibular apparatus. Along with its actions as an antagonist at H1-receptors, meclizine also possesses anticholinergic, central nervous system depressant, and local anesthetic effects. Meclizine depresses labyrinth excitability and vestibular stimulation and may affect the medullary chemoreceptor trigger zone. It is sold under the brand names Bonine, Bonamine, Antivert, Postafen, Sea Legs, and Dramamine II.
CNS Activity
Sources: http://www.drugbank.ca/drugs/DB00737
Curator's Comment:: central nervous system depressant
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26239802 |
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Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26239802 |
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Target ID: Q922E4 Gene ID: 68671.0 Gene Symbol: Pcyt2 Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24142790 |
31.0 µM [Ki] | ||
Target ID: CHEMBL231 Sources: http://www.drugbank.ca/drugs/DB00737 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ANTIVERT Approved UseEffective: Management of nausea and vomiting, and dizziness associated with motion sickness.
Possibly Effective: Management of vertigo associated with diseases affecting the vestibular system. Launch Date1.33565763E12 |
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Primary | ANTIVERT Approved UseEffective: Management of nausea and vomiting, and dizziness associated with motion sickness.
Possibly Effective: Management of vertigo associated with diseases affecting the vestibular system. Launch Date1.33565763E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
99.43 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21903894/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECLIZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
564.03 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21903894/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECLIZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21903894/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECLIZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
25 mg 2 times / day multiple, oral Recommended Dose: 25 mg, 2 times / day Route: oral Route: multiple Dose: 25 mg, 2 times / day Sources: |
unhealthy, 5-10 n = 6 Health Status: unhealthy Condition: Achondroplasia Age Group: 5-10 Sex: M+F Population Size: 6 Sources: |
|
25 mg single, oral Recommended |
unhealthy, 6-10 n = 6 Health Status: unhealthy Condition: Achondroplasia Age Group: 6-10 Sex: M+F Population Size: 6 Sources: |
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100 mg multiple, oral (total daily dose) Recommended Dose: 100 mg Route: oral Route: multiple Dose: 100 mg Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Vertigo Sources: Page: p.1 |
Other AEs: Drowsiness... Other AEs: Drowsiness Sources: Page: p.1 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Drowsiness | 100 mg multiple, oral (total daily dose) Recommended Dose: 100 mg Route: oral Route: multiple Dose: 100 mg Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Vertigo Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
---|---|---|
Spectrophotometric determination of meclozine HCl and papaverine HCl in their pharmaceutical formulations. | 2002 Apr 15 |
|
Auditory hallucinations elicited by combined meclizine and metaxalone use at bedtime. | 2004 Nov |
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Multi-species analyses of direct activators of the constitutive androstane receptor. | 2011 Oct |
|
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/meclizine.html
Usual Adult Dose for Vertigo
-25 to 100 mg orally per day in divided doses
Usual Adult Dose for Motion Sickness
-Initial Dose: 25 to 50 mg orally 1 hour before travel
-Maintenance Dose: Repeat dose every 24 hours if needed
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24142790
50 uM meclizine inhibited respiratory growth of human skin fibroblasts
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 06:53:00 UTC 2021
by
admin
on
Sat Jun 26 06:53:00 UTC 2021
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Record UNII |
3L5TQ84570
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Record Status |
Validated (UNII)
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Record Version |
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Official Name | English | ||
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29578
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WHO-ATC |
R06AE05
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WHO-ATC |
R06AE55
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WHO-VATC |
QR06AE55
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LIVERTOX |
587
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WHO-VATC |
QR06AE05
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NDF-RT |
N0000178372
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NCI_THESAURUS |
C267
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NDF-RT |
N0000009034
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NDF-RT |
N0000009034
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Code System | Code | Type | Description | ||
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6676
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PRIMARY | RxNorm | ||
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DB00737
Created by
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PRIMARY | |||
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4034
Created by
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PRIMARY | |||
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MECLOZINE
Created by
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PRIMARY | |||
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CHEMBL1623
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PRIMARY | |||
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SUB08685MIG
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PRIMARY | |||
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C61610
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PRIMARY | |||
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Meclizine
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PRIMARY | |||
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3L5TQ84570
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PRIMARY | |||
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1649
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PRIMARY | |||
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M7118
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PRIMARY | Merck Index | ||
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2757
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PRIMARY | |||
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209-323-3
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D008468
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3113
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204
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PRIMARY | |||
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569-65-3
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PRIMARY | |||
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569-65-3
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PRIMARY |
Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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ENANTIOMER -> RACEMATE | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
RECOMBINANT ENZYME
SUBSTRATE
Km
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METABOLIC ENZYME -> SUBSTRATE |
SUBSTRATE
Vmax
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |