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MedKoo Cat#: 464682 | Name: Cinnarizine-d8

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cinnarizine-d8 is intended for use as an internal standard for the quantification of cinnarizine by GC- or LC-MS. Cinnarizine is a calcium channel inhibitor and histamine H4 receptor antagonist (Ki = 142 nM). It inhibits L- and T-type calcium channels in isolated guinea pig atrial cells in a voltage-dependent manner. Cinnarizine inhibits L-type calcium currents in isolated guinea pig type II vestibular hair cells (IC50 = 1.5 µM). In vivo, cinnarizine (10 mg/kg) inhibits ethanol-induced gastric ulcer formation in rats. Formulations containing cinnarizine have been used in the treatment of nausea and vomiting due to vertigo, Meniere's disease, or chemotherapy.

Chemical Structure

Cinnarizine-d8
Cinnarizine-d8
CAS#1185242-27-6

Theoretical Analysis

MedKoo Cat#: 464682

Name: Cinnarizine-d8

CAS#: 1185242-27-6

Chemical Formula: C26H20D8N2

Exact Mass: 376.2755

Molecular Weight: 376.57

Elemental Analysis: C, 82.93; H, 9.63; N, 7.44

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Synonym
Cinnarizine-d8; Cinnarizine d8;
IUPAC/Chemical Name
1-benzhydryl-4-cinnamylpiperazine-2,2,3,3,5,5,6,6-d8
InChi Key
DERZBLKQOCDDDZ-RVEWZOGKSA-N
InChi Code
InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2/b13-10+/i19D2,20D2,21D2,22D2
SMILES Code
[2H]C1(C([2H])(N(C([2H])(C([2H])(N1C(C2=CC=CC=C2)C3=CC=CC=C3)[2H])[2H])C/C=C/C4=CC=CC=C4)[2H])[2H]
Appearance
Solid 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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 376.57 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.

Recalculate based on batch purity %
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
1: Plescia F, Salvago P, Dispenza F, Messina G, Cannizzaro E, Martines F. Efficacy and Pharmacological Appropriateness of Cinnarizine and Dimenhydrinate in the Treatment of Vertigo and Related Symptoms. Int J Environ Res Public Health. 2021 Apr 30;18(9):4787. doi: 10.3390/ijerph18094787. PMID: 33946152. 2: Shahba AA, Tashish AY, Alanazi FK, Kazi M. Combined Self-Nanoemulsifying and Solid Dispersion Systems Showed Enhanced Cinnarizine Release in Hypochlorhydria/Achlorhydria Dissolution Model. Pharmaceutics. 2021 Apr 28;13(5):627. doi: 10.3390/pharmaceutics13050627. PMID: 33924928. 3: Klitgaard M, Müllertz A, Berthelsen R. Estimating the Oral Absorption from Self-Nanoemulsifying Drug Delivery Systems Using an In Vitro Lipolysis- Permeation Method. Pharmaceutics. 2021 Apr 2;13(4):489. doi: 10.3390/pharmaceutics13040489. PMID: 33918449; PMCID: PMC8065752. 4: Cinnarizine/dimenhydrinate for vertigo. Aust Prescr. 2021 Apr;44(2):62-63. doi: 10.18773/austprescr.2021.009. Epub 2021 Mar 4. PMID: 33911336; PMCID: PMC8075741. 5: Francke NM, Bunjes H. Drug localization and its effect on the physical stability of poloxamer 188-stabilized colloidal lipid emulsions. Int J Pharm. 2021 Apr 15;599:120394. doi: 10.1016/j.ijpharm.2021.120394. Epub 2021 Mar 3. PMID: 33675931. 6: Lai A, Sahbaz Y, Ford L, Nguyen TH, Haque S, Williams HD, Benameur H, Scammells PJ, Porter CJH. Stabilising disproportionation of lipophilic ionic liquid salts in lipid-based formulations. Int J Pharm. 2021 Mar 15;597:120292. doi: 10.1016/j.ijpharm.2021.120292. Epub 2021 Feb 11. PMID: 33581479. 7: Brinkmann J, Becker I, Kroll P, Luebbert C, Sadowski G. Predicting the API partitioning between lipid-based drug delivery systems and water. Int J Pharm. 2021 Feb 15;595:120266. doi: 10.1016/j.ijpharm.2021.120266. Epub 2021 Jan 21. PMID: 33486017. 8: Ilie AR, Griffin BT, Vertzoni M, Kuentz M, Kolakovic R, Prudic-Paus A, Malash A, Bohets H, Herman J, Holm R. Exploring precipitation inhibitors to improve in vivo absorption of cinnarizine from supersaturated lipid-based drug delivery systems. Eur J Pharm Sci. 2021 Apr 1;159:105691. doi: 10.1016/j.ejps.2020.105691. Epub 2020 Dec 24. PMID: 33359616. 9: Brinkmann J, Exner L, Luebbert C, Sadowski G. In-Silico Screening of Lipid- Based Drug Delivery Systems. Pharm Res. 2020 Nov 23;37(12):249. doi: 10.1007/s11095-020-02955-0. PMID: 33230602; PMCID: PMC7683453. 10: Mangla B, Jain A, Malik DS. Exploring the Potentials of Corn Fiber Gum in Fabricating Mucoadhesive Floating Tablet of Poorly Gastro-retainable Drug. Recent Pat Antiinfect Drug Discov. 2020 Nov 11. doi: 10.2174/1574891X15999201111200523. Epub ahead of print. PMID: 33183208. 11: Kitchens BP, Snyder RJ, Cuffy CA. A Literature Review of Pharmacological Agents to Improve Venous Leg Ulcer Healing. Wounds. 2020 Jul;32(7):195-207. PMID: 33166265. 12: Ilie AR, Griffin BT, Vertzoni M, Kuentz M, Cuyckens F, Wuyts K, Kolakovic R, Holm R. Toward simplified oral lipid-based drug delivery using mono-/di- glycerides as single component excipients. Drug Dev Ind Pharm. 2020 Dec;46(12):2051-2060. doi: 10.1080/03639045.2020.1843475. Epub 2020 Nov 9. PMID: 33124918. 13: Abdelmonem R, Hamed RR, Abdelhalim SA, ElMiligi MF, El-Nabarawi MA. Formulation and Characterization of Cinnarizine Targeted Aural Transfersomal Gel for Vertigo Treatment: A Pharmacokinetic Study on Rabbits. Int J Nanomedicine. 2020 Aug 19;15:6211-6223. doi: 10.2147/IJN.S258764. PMID: 32904111; PMCID: PMC7450212. 14: Wang H, Li S, Liu L, Wang J, Wang Y, Guo W. Interactions between dipfluzine- based complexes and cytochrome P450 enzymes: Information on salt, cocrystal, and salt cocrystal complexes. Environ Toxicol Pharmacol. 2020 Nov;80:103487. doi: 10.1016/j.etap.2020.103487. Epub 2020 Sep 1. PMID: 32889110. 15: Türkeş C, Demir Y, Beydemir Ş. Some calcium-channel blockers: kinetic and in silico studies on paraoxonase-I. J Biomol Struct Dyn. 2020 Aug 12:1-9. doi: 10.1080/07391102.2020.1806927. Epub ahead of print. PMID: 32783605. 16: Vo AQ, Zhang J, Nyavanandi D, Bandari S, Repka MA. Hot melt extrusion paired fused deposition modeling 3D printing to develop hydroxypropyl cellulose based floating tablets of cinnarizine. Carbohydr Polym. 2020 Oct 15;246:116519. doi: 10.1016/j.carbpol.2020.116519. Epub 2020 Jun 4. PMID: 32747229; PMCID: PMC7403534. 17: Olusesi A, Oyeniran O. Persistence of Non-Vertigo Symptoms in Meniere Disease During Remission - A Preliminary Report. Otolaryngol Pol. 2020 Feb 5;74(4):31-36. doi: 10.5604/01.3001.0013.7927. PMID: 32636348. 18: Togha M, Martami F, Abdollahi M, Mozafari M, Cheraghali H, Rafiee P, Shafaei M. Cinnarizine as an alternative recommendation for migraine prophylaxis: a narrative review. Expert Rev Neurother. 2020 Sep;20(9):943-951. doi: 10.1080/14737175.2020.1787834. Epub 2020 Jul 9. PMID: 32597267. 19: Bertoni S, Albertini B, Passerini N. Different BCS Class II Drug-Gelucire Solid Dispersions Prepared by Spray Congealing: Evaluation of Solid State Properties and In Vitro Performances. Pharmaceutics. 2020 Jun 12;12(6):548. doi: 10.3390/pharmaceutics12060548. PMID: 32545643; PMCID: PMC7356387. 20: Wang H, Li S, Wang X, He C, Wang T, Wang Y, Guo W. Vasodilation activity of dipfluzine metabolites in isolated rat basilar arteries and their underlying mechanisms. Environ Toxicol Pharmacol. 2020 Oct;79:103430. doi: 10.1016/j.etap.2020.103430. Epub 2020 Jun 13. PMID: 32544426.