Levocetirizine | CAS#130018-77-8

MedKoo Cat#: 341328 | Name: Levocetirizine

Description:

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

Levocetirizine is simply the isolated levorotary enantiomer of cetirizine,

Chemical Structure

Levocetirizine

CAS#130018-77-8 (free acid)

Theoretical Analysis

MedKoo Cat#: 341328

Name: Levocetirizine

CAS#: 130018-77-8 (free acid)

Chemical Formula: C21H25ClN2O3

Exact Mass: 388.1554

Molecular Weight: 388.89

Elemental Analysis: C, 64.86; H, 6.48; Cl, 9.12; N, 7.20; O, 12.34

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

130018-77-8 (free acid) 130018-87-0 (2HCl)

Synonym

Levocetirizine; Xarlin; Xusal.

IUPAC/Chemical Name

Acetic acid, (2-(4-((R)-(4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-

InChi Key

ZKLPARSLTMPFCP-OAQYLSRUSA-N

InChi Code

InChI=1S/C21H25ClN2O3/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)/t21-/m1/s1

SMILES Code

OC(=O)COCCN1CCN(CC1)[C@H](c2ccccc2)c3ccc(Cl)cc3

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

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Levocetirizine ((R)-Cetirizine) is a third-generation peripheral H1-receptor antagonist.

In vitro activity:

The addition of levocetirizine to eosinophil cultures caused a dose-dependent decrease in the ability of cells to produce RANTES and eotaxin in response to antigen stimulation, and the minimum concentration that caused a significant decrease was 0.05 μM. Reference: In Vivo. 2014 Jul-Aug;28(4):657-66. https://pubmed.ncbi.nlm.nih.gov/24982238/

In vivo activity:

Levocetirizine attenuated lung edema and mitigated the increases in BALF protein levels, LDH activity, and lung leukocyte recruitment in LPS-challenged rats. Additionally, TNF-α protein levels in BALF and lung tissue were diminished by levocetirizine administration. Levocetirizine also exhibited a potent antioxidant activity as indicated by a decrease in lung tissue levels of malondialdehyde and an enhancement of superoxide dismutase activity. Reference: Biomed Res Int. 2018 Aug 13;2018:7019759. https://pubmed.ncbi.nlm.nih.gov/30186866/

Preparing Stock Solutions

The following data is based on the product molecular weight 388.89 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

Formulation protocol:

1. Kanei A, Asano K, Kanai K, Furuta A, Sasaki K, Suzaki H. Inhibitory action of levocetirizine on the production of eosinophil chemoattractants RANTES and eotaxin in vitro and in vivo. In Vivo. 2014 Jul-Aug;28(4):657-66. PMID: 24982238. 2. Komatsuzaki T, Suzaki I, Hirano K, Kanai K, Asano K, Suzaki H. Suppression of osteopontin functions by levocetirizine, a histamine H1 receptor antagonist, in vitro. Biomed Res Int. 2013;2013:735835. doi: 10.1155/2013/735835. Epub 2013 Dec 30. PMID: 24490170; PMCID: PMC3893813. 3. Fahmi ANA, Shehatou GSG, Salem HA. Levocetirizine Pretreatment Mitigates Lipopolysaccharide-Induced Lung Inflammation in Rats. Biomed Res Int. 2018 Aug 13;2018:7019759. doi: 10.1155/2018/7019759. PMID: 30186866; PMCID: PMC6110004. 4. Nakasone T, Wakuda H, Sugimoto Y, Kamei C. Effects of ICI204,448, naloxone methiodide and levocetirizine on the scratching behavior induced by a κ-opioid antagonist, nor-BNI, in ICR mice. Immunopharmacol Immunotoxicol. 2017 Oct;39(5):292-295. doi: 10.1080/08923973.2017.1354879. Epub 2017 Jul 26. PMID: 28745076.

In vitro protocol:

In vivo protocol:

1. Fahmi ANA, Shehatou GSG, Salem HA. Levocetirizine Pretreatment Mitigates Lipopolysaccharide-Induced Lung Inflammation in Rats. Biomed Res Int. 2018 Aug 13;2018:7019759. doi: 10.1155/2018/7019759. PMID: 30186866; PMCID: PMC6110004. 2. Nakasone T, Wakuda H, Sugimoto Y, Kamei C. Effects of ICI204,448, naloxone methiodide and levocetirizine on the scratching behavior induced by a κ-opioid antagonist, nor-BNI, in ICR mice. Immunopharmacol Immunotoxicol. 2017 Oct;39(5):292-295. doi: 10.1080/08923973.2017.1354879. Epub 2017 Jul 26. PMID: 28745076.

1: Weinberger M, Hendeles L. Nonprescription medications for respiratory symptoms: Facts and marketing fictions. Allergy Asthma Proc. 2018 May 1;39(3):169-176. doi: 10.2500/aap.2018.39.4117. PubMed PMID: 29669663. 2: Kikuchi A, Nasir FBM, Inami A, Mohsen A, Watanuki S, Miyake M, Takeda K, Koike D, Ito T, Sasakawa J, Matsuda R, Hiraoka K, Maurer M, Yanai K, Watabe H, Tashiro M. Effects of levocetirizine and diphenhydramine on regional glucose metabolic changes and hemodynamic responses in the human prefrontal cortex during cognitive tasks. Hum Psychopharmacol. 2018 Mar;33(2):e2655. doi: 10.1002/hup.2655. Epub 2018 Mar 13. PubMed PMID: 29532516; PubMed Central PMCID: PMC5900896. 3: Domagała A, Szepietowski J, Reich A. Antihistamines in the treatment of pruritus in psoriasis. Postepy Dermatol Alergol. 2017 Oct;34(5):457-463. doi: 10.5114/ada.2017.71112. Epub 2017 Oct 31. PubMed PMID: 29507561; PubMed Central PMCID: PMC5831281. 4: Okubo K, Uchida E, Terahara T, Akiyama K, Kobayashi S, Tanaka Y. Efficacy and safety of emedastine patch, a novel transdermal drug delivery system for allergic rhinitis: Phase III, multicenter, randomized, double-blinded, placebo-controlled, parallel-group comparative study in patients with seasonal allergic rhinitis. Allergol Int. 2018 Jan 29. pii: S1323-8930(17)30189-2. doi: 10.1016/j.alit.2017.12.005. [Epub ahead of print] PubMed PMID: 29395965. 5: Marrouche N, Williams HC. Letter in response to "Effectiveness and safety of levocetirizine 10 mg versus a combination of levocetirizine 5 mg and montelukast 10 mg in chronic urticaria resistant to levocetirizine 5 mg: A double-blind, randomized, controlled trial" by Sarkar et al.. Indian J Dermatol Venereol Leprol. 2018 Jan-Feb;84(1):59-60. doi: 10.4103/ijdvl.IJDVL_860_17. PubMed PMID: 29271368. 6: Godse KV, Nadkarni N, Patil S, Mehta A. Subcutaneous Autologous Serum Therapy in Chronic Spontaneous Urticaria. Indian J Dermatol. 2017 Sep-Oct;62(5):505-507. doi: 10.4103/ijd.IJD_710_16. PubMed PMID: 28979013; PubMed Central PMCID: PMC5618838. 7: Poluzzi E, Diemberger I, De Ridder M, Koci A, Clo M, Oteri A, Pecchioli S, Bezemer I, Schink T, Pilgaard Ulrichsen S, Boriani G, Sturkenboom MCJ, De Ponti F, Trifirò G. Use of antihistamines and risk of ventricular tachyarrhythmia: a nested case-control study in five European countries from the ARITMO project. Eur J Clin Pharmacol. 2017 Nov;73(11):1499-1510. doi: 10.1007/s00228-017-2317-0. Epub 2017 Aug 22. PubMed PMID: 28831527. 8: An I, Demir V, Ibiloglu I, Akdeniz S. Fixed Drug Eruption Induced by Levocetirizine. Indian Dermatol Online J. 2017 Jul-Aug;8(4):276-278. doi: 10.4103/idoj.IDOJ_348_16. PubMed PMID: 28761848; PubMed Central PMCID: PMC5518583. 9: Kolkhir P, Pogorelov D, Olisova O. CRP, D-dimer, fibrinogen and ESR as predictive markers of response to standard doses of levocetirizine in patients with chronic spontaneous urticaria. Eur Ann Allergy Clin Immunol. 2017 Jul;49(4):189-192. PubMed PMID: 28752724. 10: Nakasone T, Wakuda H, Sugimoto Y, Kamei C. Effects of ICI204,448, naloxone methiodide and levocetirizine on the scratching behavior induced by a κ-opioid antagonist, nor-BNI, in ICR mice. Immunopharmacol Immunotoxicol. 2017 Oct;39(5):292-295. doi: 10.1080/08923973.2017.1354879. Epub 2017 Jul 26. PubMed PMID: 28745076. 11: Carnovale C, Russo S, Biondelli G, Gentili M, Pozzi M, Antoniazzi S, Radice S, Clementi E. Levocetirizine-induced Psychiatric Disorders in a Pediatric Patient: A Case Report and a Pharmacovigilance Database Analysis. J Pharmacol Pharmacother. 2017 Apr-Jun;8(2):74-76. doi: 10.4103/jpp.JPP_14_17. PubMed PMID: 28706402; PubMed Central PMCID: PMC5497403. 12: Sarkar TK, Sil A, Pal S, Ghosh C, Das NK. Effectiveness and safety of levocetirizine 10 mg versus a combination of levocetirizine 5 mg and montelukast 10 mg in chronic urticaria resistant to levocetirizine 5 mg: A double-blind, randomized, controlled trial. Indian J Dermatol Venereol Leprol. 2017 Sep-Oct;83(5):561-568. doi: 10.4103/ijdvl.IJDVL_551_16. PubMed PMID: 28656910. 13: Motola D, Donati M, Biagi C, Calamelli E, Cipriani F, Melis M, Monaco L, Vaccheri A, Ricci G. Safety profile of H1-antihistamines in pediatrics: an analysis based on data from VigiBase. Pharmacoepidemiol Drug Saf. 2017 Oct;26(10):1164-1171. doi: 10.1002/pds.4246. Epub 2017 Jun 27. PubMed PMID: 28653802. 14: Paśko P, Rodacki T, Domagała-Rodacka R, Palimonka K, Marcinkowska M, Owczarek D. Second generation H1 - antihistamines interaction with food and alcohol-A systematic review. Biomed Pharmacother. 2017 Sep;93:27-39. doi: 10.1016/j.biopha.2017.06.008. Epub 2017 Jun 13. Review. PubMed PMID: 28622592. 15: Goyal V, Gupta A, Gupta O, Lal D, Gill M. Comparative Efficacy and Safety of Ebastine 20 mg, Ebastine 10 mg and Levocetirizine 5 mg in Acute Urticaria. J Clin Diagn Res. 2017 Mar;11(3):WC06-WC09. doi: 10.7860/JCDR/2017/23961.9550. Epub 2017 Mar 1. PubMed PMID: 28511488; PubMed Central PMCID: PMC5427414. 16: Barniol C, Dehours E, Mallet J, Houze-Cerfon CH, Lauque D, Charpentier S. Levocetirizine and Prednisone Are Not Superior to Levocetirizine Alone for the Treatment of Acute Urticaria: A Randomized Double-Blind Clinical Trial. Ann Emerg Med. 2018 Jan;71(1):125-131.e1. doi: 10.1016/j.annemergmed.2017.03.006. Epub 2017 May 3. PubMed PMID: 28476259. 17: Noguchi S, Nishimura T, Mukaida S, Benet LZ, Nakashima E, Tomi M. Cellular Uptake of Levocetirizine by Organic Anion Transporter 4. J Pharm Sci. 2017 Sep;106(9):2895-2898. doi: 10.1016/j.xphs.2017.03.026. Epub 2017 Apr 4. PubMed PMID: 28385546. 18: Abo Dena AS, Abdel Gaber SA. In vitro drug interaction of levocetirizine and diclofenac: Theoretical and spectroscopic studies. Spectrochim Acta A Mol Biomol Spectrosc. 2017 Jun 15;181:239-248. doi: 10.1016/j.saa.2017.03.043. Epub 2017 Mar 20. PubMed PMID: 28371723. 19: Jung MC, Kim JK, Cho JY, Song JW, Lee B, Park JW, Seo J, Kim SE. A case of levocetirizine-induced liver injury. Clin Mol Hepatol. 2016 Dec;22(4):495-498. doi: 10.3350/cmh.2016.0023. Epub 2016 Dec 25. PubMed PMID: 28081586; PubMed Central PMCID: PMC5266344. 20: Snidvongs K, Seresirikachorn K, Khattiyawittayakun L, Chitsuthipakorn W. Sedative Effects of Levocetirizine: A Systematic Review and Meta-Analysis of Randomized Controlled Studies. Drugs. 2017 Feb;77(2):175-186. doi: 10.1007/s40265-016-0682-0. Review. PubMed PMID: 28070872.