Loratadine

Base Information

• Chemical Name: Loratadine
• CAS No.: 79794-75-5
• Molecular Formula: C22H23ClN2O2
• Molecular Weight: 382.89
• Hs Code.: DERIVATION
• European Community (EC) Number: 935-907-9,616-734-5
• NSC Number: 758628,721075
• UNII: 7AJO3BO7QN
• DSSTox Substance ID: DTXSID2023224
• Nikkaji Number: J23.749C
• Wikipedia: Loratadine
• Wikidata: Q424049
• NCI Thesaurus Code: C29162
• RXCUI: 28889
• Pharos Ligand ID: RPFNHPTN1B5F
• Metabolomics Workbench ID: 38693
• ChEMBL ID: CHEMBL998
• Mol file: 79794-75-5.mol

Synonyms:4-(8-Chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylic Acid Ethyl Ester;Alavert;Claritin;Clarium;Loratadine;Sch 29851;Sch-29851;Sch29851

Chemical Property of Loratadine

Chemical Property:

• Appearance/Colour: white crystalline solid
• Melting Point: 134-136 ºC
• Boiling Point: 531.3 ºC at 760 mmHg
• PKA: 4.27±0.20(Predicted)
• Flash Point: 275.1 ºC
• PSA: 42.43000
• Density: 1.261 g/cm³
• LogP: 4.82570
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 26 mg/mL, soluble
• Water Solubility.: It is soluble in DMSO (50 mg/ml), ethanol (77 mg/ml at 25°C), water (<1 mg/ml at 25°C), chloroform, and methanol.
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 382.1448057
• Heavy Atom Count: 27
• Complexity: 569

Purity/Quality:

99% ^*data from raw suppliers

Loratidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1CCC(=C2C3=C(CCC4=C2N=CC=C4)C=C(C=C3)Cl)CC1
• Recent ClinicalTrials: Gabapentin Versus Loratadine in Uremic Pruritus
• Recent EU Clinical Trials: Phase-II randomized clinical trial to evaluate the effect of Loratadine associated with Rapamune on Lymphagioleiomyomatosis (LAM).
• Recent NIPH Clinical Trials: Histamine H1 receptor occupancy of amino group-containing non-sedating antihistamines measured by PET in healthy male volunteers
• Drug Interactions: Inhibition of hepatic drug-metabolizing enzyme function drugs can slow the metabolism of the product, such as itraconazole, ketoconazole, Daily with 400 mg ketoconazole suit, can make the product and its active metabolite to carboxyethyl loratadine increased plasma concentrations, but it was not observed in the changes of electrocardiogram (ECG). It can also inhibit the metabolism of loratadine when used with macrolides, cimetidine, theophylline and other drugs together.
• Description: Loratadine is a non-sedating antihistamine indicated for use in allergic rhinitis and chronic urticaria. Its major advantage over other non-sedating antihistamines such as astemizole and terfenadine is its very fast onset of action. Loratadine is claimed not to cross the blood-brain barrier.
• Uses: antinflammatory, analgesic, antipyretic A nonsedating-type histamine H1-receptor Loratadine, is used as a peripheral histamine H1 receptor agonist. It is also used as an orally active antiallergic agent. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.
• Indications: Loratadine (Claritin) is a long-acting, potent peripheral H1 blocker with minimal sedative effects. It does not appear to have the same adverse cardiac effects as the other nonsedating H1 antihistamines. It is indicated for allergic rhinitis and chronic urticaria.
• Clinical Use: Loratadine is related to the first-generation tricyclic antihistamines and to antidepressants. It is nonsedating, and neither it nor its major metabolite, desloratadine (descarboethoxyloratadine), is associated with the potentially cardiotoxic effects reported for terfenadine and astemizole. On chronic dosing, the AUC (plasma concentration–time curve) for the metabolite is greater than that for the parent drug, and its half-life is longer.
• Drug interactions: Molecular weight (daltons) 382.9 % Protein binding 97-99 % Excreted unchanged in urine 40 Volume of distribution (L/kg) No data Half-life - normal/ESRF (hrs) 12-15 / Unchanged

Technology Process of Loratadine

There total 21 articles about Loratadine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

chloroformic acid ethyl ester (541-41-3) + N-methyldesloratadine (38092-89-6) → loratadine (79794-75-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In toluene; at 60 - 75 ℃; for 1 - 2h;

Reference yield: 82.0%

diethyl N-ethoxycarbonylpiperidine-4-phosphonate (216870-24-5) → loratadine (79794-75-5)

Guidance literature:

With hydrogenchloride; In N,N-dimethyl acetamide; isopropyl alcohol; at 20 - 140 ℃; for 2h; under 760.051 Torr;

Reference yield: 40.0%

→ loratadine (79794-75-5)

Guidance literature:

upstream raw materials:

chloroformic acid ethyl ester

N-methyldesloratadine

2-cyano-3-methylpyridine

N-tert-butyl-3-methylpyridine-2-carboxamide

Downstream raw materials:

4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-cyclohexyl-1-piperidinecarbothioamide

4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-phenyl-1-piperidinecarbothioamide

4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-(2-methylphenyl)-1-piperidinecarbothioamide

6-Hydroxydesloratadine

Refernces

• 1、 Chernowsky, Colleen P.,Chmiel, Alyah F.,Wickens, Zachary K.,Williams, Oliver P.,Yeung, Charles S.. "Non-innocent Radical Ion Intermediates in Photoredox Catalysis: Parallel Reduction Modes Enable Coupling of Diverse Aryl Chlorides". supporting information. p. 10882 - 10889. Retrieved 2021/07/31.
• 2、 Cuboni, Serena,Devigny, Christian,Hoogeland, Bastiaan,Strasser, Andrea,Pomplun, Sebastian,Hauger, Barbara,H?fner, Georg,Wanner, Klaus T.,Eder, Matthias,Buschauer, Armin,Holsboer, Florian,Hausch, Felix. "Loratadine and analogues: Discovery and preliminary structure-activity relationship of inhibitors of the amino acid transporter B0AT2". supporting information. p. 9473 - 9479. Retrieved 2015/01/09.