Synonym
Meclizine hydrochloride; Meclizine dihydrochloride monohydrate; Meclizine Hcl; C25H27ClN2.2HCl.H2O; Roberts Brand of Meclizine Dihydrochloride; Ru Vert M; Ru-Vert-M; RuVertM; Torrens Brand of Meclizine Dihydrochloride;
IUPAC/Chemical Name
1-[(4-chlorophenyl)-phenylmethyl]-4-[(3-methylphenyl)methyl]piperazine dihydrochloride
InChi Key
VCTHNOIYJIXQLV-UHFFFAOYSA-N
InChi Code
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
SMILES Code
CC1=CC(CN2CCN(C(C3=CC=C(Cl)C=C3)C4=CC=CC=C4)CC2)=CC=C1.[H]Cl.[H]Cl
Appearance
White to light yellow crystalline powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Meclizine (NSC 28728) is a histamine H1 receptor antagonist.
In vitro activity:
The protection of meclizine was tested in primary rat cortical cultures highly enriched with neurons (supplementary S1). 6-OHDA induced a dose-dependent increase of Fluoro-jade C (FJ-C) stain, which reflected the neuronal death (supplementary S2A,B). The concentration of 10 μM 6-OHDA was chosen because of remarkable but not overwhelming effect of cell death (21.10 ± 5.37% FJ-C stained cells compared with no-toxin control: 6.65 ± 0.67% FJ-C stained cells). Compared with control, 3.125 μM of meclizine treatment, which was determined by the dose-dependent experiments of the protection of meclizine against 6-OHDA (supplementary S2C), for 24 hours did not increase the neuronal death detected by FJ-C stain. Upon 10 μM of 6-OHDA treatment for 24 hours, 3.125 μM meclizine significantly reduced the neuronal death release from 20.38 ± 1.57% to 12.68 ± 0.74% (p < 0.001) (Fig. 1A). The protection of meclizine was also confirmed by the LDH release assay: upon 10 μM of 6-OHDA treatment for 24 hours, 3.125 μM meclizine significantly reduced LDH release from 10.8 ± 1.4% to 6.8 ± 0.9% (p < 0.05) (Fig. 1B). Propidium iodide binding assay confirmed the protection by meclizine in primary rat cortical cultures (Fig. 1C).
Reference: Sci Rep. 2016 May 5;6:25344. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/27145922/
In vivo activity:
Dementia was induced in mice by intacerebroventricular administration of streptozotocin (STZ) followed by treatment with meclizine, a PXR agonist, and subsequently exposed to the Morris water maze test and biochemical and histopathological analysis to evaluate the effect on cognition. STZ-treated mice exhibited significant enhancement in brain thiobarbituric acid reactive species, interleukin-1β, tumour necrosis factor-α, myeloperoxidase, and acetylcholinestrase activity in addition to diminution in glutathione levels and superoxide dismutase activity in comparison to untreated mice. Administration of meclizine to STZ mice recuperated cognition and biochemical alterations. Concomitant administration of ketoconazole, a PXR antagonist, with meclizine prevented the protective effects. The upshots of our study proclaim that meclizine protects cognitive deficits by virtue of its antioxidant, anticholinesterase, and antiinflammatory properties. Results also signify the potential of PXR in neuroprotective actions of meclizine in dementia.
Reference: Can J Physiol Pharmacol. 2020 Jun;98(6):383-390. https://cdnsciencepub.com/doi/10.1139/cjpp-2019-0421?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%20%200pubmed
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
4.0 |
8.62 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
463.87
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
In vitro protocol:
1. Hong CT, Chau KY, Schapira AH. Meclizine-induced enhanced glycolysis is neuroprotective in Parkinson disease cell models. Sci Rep. 2016 May 5;6:25344. doi: 10.1038/srep25344. PMID: 27145922; PMCID: PMC4857109.
2. Gohil VM, Offner N, Walker JA, Sheth SA, Fossale E, Gusella JF, MacDonald ME, Neri C, Mootha VK. Meclizine is neuroprotective in models of Huntington's disease. Hum Mol Genet. 2011 Jan 15;20(2):294-300. doi: 10.1093/hmg/ddq464. Epub 2010 Oct 25. PMID: 20977989; PMCID: PMC3005902.
In vivo protocol:
1. Singh H, Sodhi RK, Chahal SK, Madan J. Meclizine ameliorates memory deficits in streptozotocin-induced experimental dementia in mice: role of nuclear pregnane X receptors. Can J Physiol Pharmacol. 2020 Jun;98(6):383-390. doi: 10.1139/cjpp-2019-0421. Epub 2020 Jan 14. PMID: 31935134.
2. Kishi S, Campanholle G, Gohil VM, Perocchi F, Brooks CR, Morizane R, Sabbisetti V, Ichimura T, Mootha VK, Bonventre JV. Meclizine Preconditioning Protects the Kidney Against Ischemia-Reperfusion Injury. EBioMedicine. 2015 Jul 29;2(9):1090-101. doi: 10.1016/j.ebiom.2015.07.035. PMID: 26501107; PMCID: PMC4588407.
1: Zhao Y, Quan P, Fang L. Preparation of an oral thin film containing meclizine
hydrochloride: In vitro and in vivo evaluation. Int J Pharm. 2015 Dec
30;496(2):314-22. doi: 10.1016/j.ijpharm.2015.10.008. Epub 2015 Oct 9. PubMed
PMID: 26456247.
2: Peraman R, Manikala M, Kondreddy VK, Yiragamreddy PR. A stability-indicating
RP-HPLC method for the quantitative analysis of meclizine hydrochloride in tablet
dosage form. J Chromatogr Sci. 2015 May-Jun;53(5):793-9. doi:
10.1093/chromsci/bmu127. Epub 2015 Feb 1. PubMed PMID: 25644814.
3: Mirza T, Lunn MJ, Keeley FJ, George RC, Bodenmiller JR. Cleaning level
acceptance criteria and a high pressure liquid chromatography procedure for the
assay of Meclizine Hydrochloride residue in swabs collected from pharmaceutical
manufacturing equipment surfaces. J Pharm Biomed Anal. 1999 Apr;19(5):747-56.
PubMed PMID: 10698538.
4: Wong CK, Urbigkit JR, Conca N, Cohen DM, Munnelly KP. GLC determination of
meclizine hydrochloride in tablet formulations. J Pharm Sci. 1973
Aug;62(8):1340-2. PubMed PMID: 4733473.
5: Grumpelt HR, Maddex BE, Nebus EJ, Rattner JC. Effects of diazepam and
meclizine hydrochloride on emotional upset due to perceptual dissonance and
motion. Percept Mot Skills. 1971 Jun;32(3):753-4. PubMed PMID: 5104948.
6: KENDRICK FJ, KING CT. ORAL ANOMALIES INDUCED IN THE RAT BY MECLIZINE
HYDROCHLORIDE. Oral Surg Oral Med Oral Pathol. 1964 Nov;18:690-6. PubMed PMID:
14199585.
7: KENDRICK FJ, WEAVER SA. ALTERATION IN AMNIOTIC FLUID VOLUME AND OTHER FINDINGS
IN MECLIZINE HYDROCHLORIDE INDUCED ANOMALIES. Proc Soc Exp Biol Med. 1963
Dec;114:747-50. PubMed PMID: 14120339.
8: LOOMIS GR. Evaluation of meclizine hydrochloride in prevention of seasickness.
Mil Med. 1955 Jul;117(1):51-3. PubMed PMID: 14393609.
9: Hom FS, Ebert WR. Determination of meclizine hydrochloride by ion-pair
extraction with methyl orange. J Pharm Sci. 1977 May;66(5):710-3. PubMed PMID:
17714.
10: Martin N, Oosterveld WJ. The vestibular effects of meclizine
hydrochloride-niacin combination (Antivert). Acta Otolaryngol. 1970
Jul;70(1):6-9. PubMed PMID: 5311676.
11: Kutscher AH, Zegarelli EV, Hyman GA, Tovell HM. A case report: prolonged use
of meclizine hydrochloride with total absence of side effects. Ann Allergy. 1966
May;24(5):246-7. PubMed PMID: 5937178.
12: KING CT. Teratogenic effects of meclizine hydrochloride on the rat. Science.
1963 Jul 26;141(3578):353-5. PubMed PMID: 14032825.
13: GUTNER LB, GOULD WJ, HANLEY JW. Effect of meclizine hydrochloride (bonamine)
upon vestibular function; observations with notes on its value in comparison with
cyclizine hydrochloride (marezine) and dimenhydrinate (dramamine). AMA Arch
Otolaryngol. 1955 Nov;62(5):497-503. PubMed PMID: 13268159.
