Cyclizine

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MedKoo CAT#: 317570

CAS#: 82-92-8 (free base)

Description: Cyclizine is an antihistamine drug used to treat nausea, vomiting and dizziness associated with motion sickness, vertigo and post-operatively following administration of general anaesthesia and opioids. Cyclizine is a histamine H1 antagonist. It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.


Chemical Structure

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Cyclizine
CAS# 82-92-8 (free base)

Theoretical Analysis

MedKoo Cat#: 317570
Name: Cyclizine
CAS#: 82-92-8 (free base)
Chemical Formula: C18H22N2
Exact Mass: 266.18
Molecular Weight: 266.380
Elemental Analysis: C, 81.16; H, 8.32; N, 10.52

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Related CAS #: 303-25-3 (HCl); 5897-18-7 (2HCl); 5897-19-8 (lactate); 303-25-3 (HCl); 82-92-8 (free base)  

Synonym: CYCLIZINE; Marezine; Ciclizina; Nautazine; Valoid; Neo-devomit

IUPAC/Chemical Name: 1-benzhydryl-4-methylpiperazine

InChi Key: UVKZSORBKUEBAZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3

SMILES Code: CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=CC=C3

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: 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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO, not in water 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 266.38 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Borukhova S, Noël T, Hessel V. Continuous-Flow Multistep Synthesis of Cinnarizine, Cyclizine, and a Buclizine Derivative from Bulk Alcohols. ChemSusChem. 2015 Dec 9. doi: 10.1002/cssc.201501367. [Epub ahead of print] PubMed PMID: 26663906.

2: Arnestad M, Eldor KB, Stray-Pedersen A, Bachs L, Karinen R. Suicide due to cyclizine overdose. J Anal Toxicol. 2014 Mar;38(2):110-2. doi: 10.1093/jat/bkt100. Epub 2013 Dec 8. PubMed PMID: 24324230.

3: Ahmadi A, Khalili M, Chavrogh S, Nahri-Niknafs B. Synthesis and Anti-inflammatory Performance of Newly Cyclizine Derivatives on Adult Male Wistar Rats. Iran J Pharm Res. 2012 Fall;11(4):1027-37. PubMed PMID: 24250533; PubMed Central PMCID: PMC3813157.

4: Wojcikiewicz TG, Peck MJ. Transient paralysis after cyclizine administration. Anaesthesia. 2013 Dec;68(12):1284-5. doi: 10.1111/anae.12515. PubMed PMID: 24219270.

5: Norman B. Transient paralysis after cyclizine administration. Anaesthesia. 2013 Dec;68(12):1284. doi: 10.1111/anae.12512. PubMed PMID: 24219268.

6: Woodfield J, St George EJ. Post-operative cyclizine misuse. Scott Med J. 2013 Nov;58(4):e1-2. doi: 10.1177/0036933013508039. PubMed PMID: 24215049.

7: McDevitt L, Mowat IR. Transient paralysis after cyclizine administration. Anaesthesia. 2013 Oct;68(10):1084. doi: 10.1111/anae.12426. PubMed PMID: 24047307.

8: Kamour A, George S, Vale A. Prolonged tachycardia following analytically confirmed cyclizine ingestion. Clin Toxicol (Phila). 2013 Jun;51(5):456-7. doi: 10.3109/15563650.2013.794283. Epub 2013 May 7. PubMed PMID: 23646828.

9: Lee P. Locked-in syndrome as a result of cyclizine administration. J Pain Symptom Manage. 2013 May;45(5):e5-7. doi: 10.1016/j.jpainsymman.2013.02.005. Epub 2013 Apr 6. PubMed PMID: 23571205.

10: Al-Shaalan NH. Extractive spectrophotometric assay of cyclizine in a pharmaceutical formulation and biological fluids. Saudi Pharm J. 2012 Jul;20(3):255-62. doi: 10.1016/j.jsps.2012.02.002. Epub 2012 Feb 21. PubMed PMID: 24115904; PubMed Central PMCID: PMC3792629. ^