Loratadine | CAS#79794-75-5 | Histamine H1 Receptor Antagonist

MedKoo Cat#: 318163 | Name: Loratadine

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Description:

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

Loratadine is a second-generation histamine H1 receptor antagonist used in the treatment of allergic rhinitis and urticaria. Unlike most classical antihistamines it lacks central nervous system depressing effects such as drowsiness. It has been shown to inhibit the release of leukotriene C4 and histamine from rodent mast cells and to inhibit allergic bronchospasm in guinea pigs. Loratadine is a selective inverse peripheral histamine H1-receptor agonist.

Chemical Structure

Loratadine

CAS#79794-75-5

Theoretical Analysis

MedKoo Cat#: 318163

Name: Loratadine

CAS#: 79794-75-5

Chemical Formula: C22H23ClN2O2

Exact Mass: 382.1448

Molecular Weight: 382.89

Elemental Analysis: C, 69.01; H, 6.05; Cl, 9.26; N, 7.32; O, 8.36

Price and Availability

Size	Price	Availability	Quantity
1g	USD 150.00	2 Weeks
5g	USD 450.00	2 Weeks

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Related CAS #

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Synonym

Loratadine; Claritin; Loratidine; Clarityn; Alavert; Loratadine Wyeth Brand; Sch 29851; Sch-29851; Sch29851; Wyeth Brand of Loratadine;

IUPAC/Chemical Name

ethyl 4-(8-chloro-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridin-11-ylidene)piperidine-1-carboxylate

InChi Key

JCCNYMKQOSZNPW-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3

SMILES Code

CCOC(=O)N1CCC(=C2C3=C(CCC4=C2N=CC=C4)C=C(C=C3)Cl)CC1

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Loratadine (SCH-29851) is a selective inverse peripheral histamine H1-receptor agonist with an IC50 of >32 μM.

In vitro activity:

Loratadine inhibited in a concentration-dependent manner the hKv1.5 current, the apparent affinity being 1.2 +/- 0.2 microM. Loratadine, 1 microM, increased the time constant of deactivation of tail currents elicited on return to -40 mV after 500 ms depolarizing pulses to +60 mV from 36.2 +/- 3.4 to 64.9 +/- 3.6 ms (n = 6, P < 0.01), thus inducing a 'crossover' phenomenon. Reference: Cardiovasc Res. 1997 Aug;35(2):341-50. https://pubmed.ncbi.nlm.nih.gov/9349397/

In vivo activity:

Loratadine (5 mg/kg) reduced mortality in S. aureus pulmonary infection model mice and acted synergistically with vancomycin to reduce pulmonary bacterial load and levels of inflammatory cytokines in bronchoalveolar lavage fluid. Reference: iScience. 2022 Jan 5;25(2):103731. https://pubmed.ncbi.nlm.nih.gov/35098100/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	78.35
	DMSO	40.1	104.84
	Ethanol	48.1	125.62

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 382.89 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. Delpón E, Valenzuela C, Gay P, Franqueza L, Snyders DJ, Tamargo J. Block of human cardiac Kv1.5 channels by loratadine: voltage-, time- and use-dependent block at concentrations above therapeutic levels. Cardiovasc Res. 1997 Aug;35(2):341-50. doi: 10.1016/s0008-6363(97)00121-1. PMID: 9349397. 2. Genovese A, Patella V, De Crescenzo G, De Paulis A, Spadaro G, Marone G. Loratadine and desethoxylcarbonyl-loratadine inhibit the immunological release of mediators from human Fc epsilon RI+ cells. Clin Exp Allergy. 1997 May;27(5):559-67. doi: 10.1046/j.1365-2222.1997.270860.x. PMID: 9179431. 3. Jang J, Hunto ST, Kim JW, Lee HP, Kim HG, Cho JY. Anti-Inflammatory Activities of an Anti-Histamine Drug, Loratadine, by Suppressing TAK1 in AP-1 Pathway. Int J Mol Sci. 2022 Apr 3;23(7):3986. doi: 10.3390/ijms23073986. PMID: 35409346; PMCID: PMC8999734. 4. Zheng J, Shang Y, Wu Y, Zhao Y, Chen Z, Lin Z, Li P, Sun X, Xu G, Wen Z, Chen J, Wang Y, Wang Z, Xiong Y, Deng Q, Qu D, Yu Z. Loratadine inhibits Staphylococcus aureus virulence and biofilm formation. iScience. 2022 Jan 5;25(2):103731. doi: 10.1016/j.isci.2022.103731. PMID: 35098100; PMCID: PMC8783127.

In vitro protocol:

In vivo protocol:

1. Jang J, Hunto ST, Kim JW, Lee HP, Kim HG, Cho JY. Anti-Inflammatory Activities of an Anti-Histamine Drug, Loratadine, by Suppressing TAK1 in AP-1 Pathway. Int J Mol Sci. 2022 Apr 3;23(7):3986. doi: 10.3390/ijms23073986. PMID: 35409346; PMCID: PMC8999734. 2. Zheng J, Shang Y, Wu Y, Zhao Y, Chen Z, Lin Z, Li P, Sun X, Xu G, Wen Z, Chen J, Wang Y, Wang Z, Xiong Y, Deng Q, Qu D, Yu Z. Loratadine inhibits Staphylococcus aureus virulence and biofilm formation. iScience. 2022 Jan 5;25(2):103731. doi: 10.1016/j.isci.2022.103731. PMID: 35098100; PMCID: PMC8783127.

1: Moukharskaya J, Abrams DM, Ashikaga T, Khan F, Schwartz J, Wilson K, Verschraegen C, Openshaw T, Valentine J, Eneman J, Unger P, Ades S. Randomized phase II study of loratadine for the prevention of bone pain caused by pegfilgrastim. Support Care Cancer. 2016 Feb 19. [Epub ahead of print] PubMed PMID: 26894485. 2: Verma S, Singh SK, Verma PR. Fabrication of lipidic nanocarriers of loratadine for facilitated intestinal permeation using multivariate design approach. Drug Dev Ind Pharm. 2016 Feb;42(2):288-306. doi: 10.3109/03639045.2015.1052078. Epub 2015 Jun 19. PubMed PMID: 26087658. 3: Chakraborty P, Parcha V, Chakraborty DD, Ghosh A. Comparative study on the predictability of statistical models (RSM and ANN) on the behavior of optimized buccoadhesive wafers containing Loratadine and their in vivo assessment. Drug Deliv. 2016 Mar;23(3):1026-37. doi: 10.3109/10717544.2014.930759. Epub 2014 Jul 3. PubMed PMID: 24988949. 4: Verma S, Singh SK. LC-ESI-MS/MS estimation of loratadine-loaded self-nanoemulsifying drug delivery systems in rat plasma: Pharmacokinetic evaluation and computer simulations by GastroPlus™. J Pharm Biomed Anal. 2016 Feb 8;124:10-21. doi: 10.1016/j.jpba.2016.02.008. [Epub ahead of print] PubMed PMID: 26922577. 5: Sherafudeen SP, Vasantha PV. Development and evaluation of in situ nasal gel formulations of loratadine. Res Pharm Sci. 2015 Nov-Dec;10(6):466-76. PubMed PMID: 26779266; PubMed Central PMCID: PMC4698857. 6: Romeo C, Li Q, Copeland L. Severe pegfilgrastim-induced bone pain completely alleviated with loratadine: A case report. J Oncol Pharm Pract. 2015 Aug;21(4):301-4. doi: 10.1177/1078155214527858. Epub 2014 Mar 24. PubMed PMID: 24664474. 7: Patel JZ, Ahenkorah S, Vaara M, Staszewski M, Adams Y, Laitinen T, Navia-Paldanius D, Parkkari T, Savinainen JR, Walczyński K, Laitinen JT, Nevalainen TJ. Loratadine analogues as MAGL inhibitors. Bioorg Med Chem Lett. 2015 Apr 1;25(7):1436-42. doi: 10.1016/j.bmcl.2015.02.037. Epub 2015 Feb 24. PubMed PMID: 25752982. 8: Li W, Doherty J, Moench P, Flarakos J, Tse FL. LC-MS/MS bioanalysis of loratadine (Claritin) in dried blood spot (DBS) samples collected by subjects in a clinical research study. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Mar 1;983-984:117-24. doi: 10.1016/j.jchromb.2014.12.033. Epub 2015 Jan 13. PubMed PMID: 25645810. 9: Li H, Tan Y, Yang L, Gao L, Wang T, Yang X, Quan D. Dissolution evaluation in vitro and bioavailability in vivo of self-microemulsifying drug delivery systems for pH-sensitive drug loratadine. J Microencapsul. 2015;32(2):175-80. doi: 10.3109/02652048.2014.985340. Epub 2014 Nov 21. PubMed PMID: 25413271. 10: Peyrovi M, Hadjmohammadi M. Extraction optimization of Loratadine by supramolecular solvent-based microextraction and its determination using HPLC. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Feb 1;980:41-7. doi: 10.1016/j.jchromb.2014.12.008. Epub 2014 Dec 30. PubMed PMID: 25579114. 11: Baumann-Birkbeck L, Grant GD, Anoopkumar-Dukie S, Kavanagh JJ. Drowsiness and motor responses to consecutive daily doses of promethazine and loratadine. Clin Neurophysiol. 2014 Dec;125(12):2390-6. doi: 10.1016/j.clinph.2014.03.026. Epub 2014 Apr 12. PubMed PMID: 24791618. 12: Kontaş S, Atlı Şekeroğlu Z. Investigation of cytotoxic and genotoxic effects of the antihistaminic drug, loratadine, on human lymphocytes. Drug Chem Toxicol. 2015 Jan;38(1):57-62. doi: 10.3109/01480545.2014.900074. Epub 2014 Mar 18. PubMed PMID: 24641298. 13: Cuboni S, Devigny C, Hoogeland B, Strasser A, Pomplun S, Hauger B, Höfner G, Wanner KT, Eder M, Buschauer A, Holsboer F, Hausch F. Loratadine and analogues: discovery and preliminary structure-activity relationship of inhibitors of the amino acid transporter B(0)AT2. J Med Chem. 2014 Nov 26;57(22):9473-9. doi: 10.1021/jm501086v. Epub 2014 Nov 7. PubMed PMID: 25318072. 14: Başak PY, Vural H, Kazanoglu OO, Erturan I, Buyukbayram HI. Effects of loratadine and cetirizine on serum levels of neuropeptides in patients with chronic urticaria. Int J Dermatol. 2014 Dec;53(12):1526-30. doi: 10.1111/ijd.12590. Epub 2014 Sep 10. PubMed PMID: 25209952. 15: Oliveira MG, Amorim WW, Rodrigues-Neto AJ. Reviewing the safety of loratadine for elderly adults: a potential shortcoming of the 2012 Beers criteria. J Am Geriatr Soc. 2014 Aug;62(8):1618-9. doi: 10.1111/jgs.12957. PubMed PMID: 25117000. 16: Hauswald B, Dill C, Boxberger J, Kuhlisch E, Zahnert T, Yarin YM. The effectiveness of acupuncture compared to loratadine in patients allergic to house dust mites. J Allergy (Cairo). 2014;2014:654632. doi: 10.1155/2014/654632. Epub 2014 Jun 5. PubMed PMID: 24995021; PubMed Central PMCID: PMC4068098. 17: Hancu G, Campian C, Rusu A, Mircia E, Kelemen H. Simultaneous determination of loratadine, desloratadine and cetirizine by capillary zone electrophoresis. Adv Pharm Bull. 2014;4(2):161-5. doi: 10.5681/apb.2014.024. Epub 2013 Dec 24. PubMed PMID: 24511480; PubMed Central PMCID: PMC3915816. 18: Arya A, Sharma V, Pathak K. Pharmaceutical evaluation and dynamic vapor sorption studies of fast dissolving intraoral films of Loratadine. Pharm Dev Technol. 2013 Nov-Dec;18(6):1329-38. doi: 10.3109/10837450.2012.685659. Epub 2012 Jun 5. PubMed PMID: 22663089. 19: Brasca R, Romero MA, Goicoechea HC, Kelterer AM, Fabian WM. Spectroscopic behavior of loratadine and desloratadine in different aqueous media conditions studied by means of TD-DFT calculations. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Nov;115:250-8. doi: 10.1016/j.saa.2013.06.037. Epub 2013 Jun 19. PubMed PMID: 23835058. 20: El-Awady M, Belal F, Pyell U. Robust analysis of the hydrophobic basic analytes loratadine and desloratadine in pharmaceutical preparations and biological fluids by sweeping-cyclodextrin-modified micellar electrokinetic chromatography. J Chromatogr A. 2013 Sep 27;1309:64-75. doi: 10.1016/j.chroma.2013.08.020. Epub 2013 Aug 9. PubMed PMID: 23953618.