Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C25H27ClN2 |
| Molecular Weight | 390.948 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(CN2CCN(CC2)[C@@H](C3=CC=CC=C3)C4=CC=C(Cl)C=C4)=CC=C1
InChI
InChIKey=OCJYIGYOJCODJL-VWLOTQADSA-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/t25-/m0/s1
| Molecular Formula | C25H27ClN2 |
| Molecular Weight | 390.948 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|||
Target ID: CHEMBL3401 |
|||
Target ID: Q922E4 Gene ID: 68671.0 Gene Symbol: Pcyt2 Target Organism: Mus musculus (Mouse) |
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 Date2012 |
|||
| 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 Date2012 |
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 |
|
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 |
|
130 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32282831/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECLIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
|
223 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32282831/ |
25 mg 2 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MECLIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FED |
|
149 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32282831/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECLIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FED |
|
131.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32282831/ |
25 mg 1 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MECLIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
|
210.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32282831/ |
25 mg 2 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MECLIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FED |
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 |
|
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 |
|
671 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32282831/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECLIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
|
2030 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32282831/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECLIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FED |
|
656 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32282831/ |
25 mg 1 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MECLIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
|
1891 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32282831/ |
25 mg 2 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MECLIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FED |
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 |
|
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 |
|
8.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32282831/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECLIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
|
3.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32282831/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
MECLIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
50 mg single, oral Recommended |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Other AEs: Drowsiness... |
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 |
|
25 mg single, oral Recommended |
unhealthy, 6-10 |
|
100 mg multiple, oral Recommended Dose: 100 mg Route: oral Route: multiple Dose: 100 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Drowsiness... Other AEs: Drowsiness Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Drowsiness | 30% | 50 mg single, oral Recommended |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Drowsiness | 100 mg multiple, oral Recommended Dose: 100 mg Route: oral Route: multiple Dose: 100 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013-09-05 |
|
| Multi-species analyses of direct activators of the constitutive androstane receptor. | 2011-10 |
|
| Withdrawal symptoms after discontinuation of transdermal scopolamine therapy: treatment with meclizine. | 2009-11-15 |
|
| Use of antiemetic drugs during pregnancy in Sweden. | 2005-12 |
|
| Auditory hallucinations elicited by combined meclizine and metaxalone use at bedtime. | 2004-11 |
|
| Meclizine is an agonist ligand for mouse constitutive androstane receptor (CAR) and an inverse agonist for human CAR. | 2004-10 |
|
| Effects of drug countermeasures for space motion sickness on working memory in humans. | 2003-12-09 |
|
| Relationship between vitamin use, smoking, and nausea and vomiting of pregnancy. | 2003-10 |
|
| Spectrophotometric and LC determination of two binary mixtures containing pyridoxine hydrochloride. | 2003-06-01 |
|
| Delivery outcome after the use of meclozine in early pregnancy. | 2003 |
|
| Discovery of molecular mechanisms of neuroprotection using cell-based bioassays and oligonucleotide arrays. | 2002-10-29 |
|
| Spectrophotometric determination of meclozine HCl and papaverine HCl in their pharmaceutical formulations. | 2002-04-15 |
|
| Pentoxifylline-induced musical hallucinations. | 1993-08 |
|
| Central nervous system effects of meclizine and dimenhydrinate: evidence of acute tolerance to antihistamines. | 1992-11 |
|
| Memory loss, confusion, and disorientation in an elderly woman taking meclizine. | 1987-05 |
|
| Clofibrate myopathy: a case report and a review of the literature. | 1986-02 |
|
| Drug-induced extrapyramidal signs in chronic liver disease--a case report. | 1977 |
Patents
Sample Use Guides
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Apr 01 16:26:37 GMT 2025
by
admin
on
Tue Apr 01 16:26:37 GMT 2025
|
| Record UNII |
LV0F32NYUF
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
189298-47-3
Created by
admin on Tue Apr 01 16:26:37 GMT 2025 , Edited by admin on Tue Apr 01 16:26:37 GMT 2025
|
PRIMARY | |||
|
6604289
Created by
admin on Tue Apr 01 16:26:37 GMT 2025 , Edited by admin on Tue Apr 01 16:26:37 GMT 2025
|
PRIMARY | |||
|
LV0F32NYUF
Created by
admin on Tue Apr 01 16:26:37 GMT 2025 , Edited by admin on Tue Apr 01 16:26:37 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
RACEMATE -> ENANTIOMER |
