Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C25H27ClN2.2ClH |
| Molecular Weight | 463.87 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.CC1=CC=CC(CN2CCN(CC2)[C@@H](C3=CC=CC=C3)C4=CC=C(Cl)C=C4)=C1
InChI
InChIKey=VCTHNOIYJIXQLV-WLOLSGMKSA-N
InChI=1S/C25H27ClN2.2ClH/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;2*1H/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 |
| 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 |
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 Date1.33565763E12 |
|||
| 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: |
|
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 |
|---|---|---|
| Drug-induced extrapyramidal signs in chronic liver disease--a case report. | 1977 |
|
| Clofibrate myopathy: a case report and a review of the literature. | 1986 Feb |
|
| Memory loss, confusion, and disorientation in an elderly woman taking meclizine. | 1987 May |
|
| Central nervous system effects of meclizine and dimenhydrinate: evidence of acute tolerance to antihistamines. | 1992 Nov |
|
| Pentoxifylline-induced musical hallucinations. | 1993 Aug |
|
| Spectrophotometric determination of meclozine HCl and papaverine HCl in their pharmaceutical formulations. | 2002 Apr 15 |
|
| Discovery of molecular mechanisms of neuroprotection using cell-based bioassays and oligonucleotide arrays. | 2002 Oct 29 |
|
| Delivery outcome after the use of meclozine in early pregnancy. | 2003 |
|
| Spectrophotometric and LC determination of two binary mixtures containing pyridoxine hydrochloride. | 2003 Jun 1 |
|
| Relationship between vitamin use, smoking, and nausea and vomiting of pregnancy. | 2003 Oct |
|
| Auditory hallucinations elicited by combined meclizine and metaxalone use at bedtime. | 2004 Nov |
|
| Effects of drug countermeasures for space motion sickness on working memory in humans. | 2004 Nov-Dec |
|
| Meclizine is an agonist ligand for mouse constitutive androstane receptor (CAR) and an inverse agonist for human CAR. | 2004 Oct |
|
| Use of antiemetic drugs during pregnancy in Sweden. | 2005 Dec |
|
| Withdrawal symptoms after discontinuation of transdermal scopolamine therapy: treatment with meclizine. | 2009 Nov 15 |
|
| 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
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
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admin
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Edited
Sat Dec 16 11:28:07 UTC 2023
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| Record UNII |
408UZ554UD
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| Record Status |
Validated (UNII)
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| Record Version |
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