13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaene

• ChemBase ID: 842
• Molecular Formular: C19H19ClN2
• Molecular Mass: 310.82056
• Monoisotopic Mass: 310.1236763
• SMILES: Clc1cc2c(C(=C3CCNCC3)c3ncccc3CC2)cc1
• Canonical SMILES: Clc1ccc2c(c1)CCc1c(C2=C2CCNCC2)nccc1
• InChI: InChI=1S/C19H19ClN2/c20-16-5-6-17-15(12-16)4-3-14-2-1-9-22-19(14)18(17)13-7-10-21-11-8-13/h1-2,5-6,9,12,21H,3-4,7-8,10-11H2
• InChIKey: JAUOIFJMECXRGI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3(8),4,6,11,13-hexaene; 13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaene; 13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene; 13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaene
• IUPAC Traditional name: clarinex; 13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaene; desloratadine
• Brand Name: Aerius; Clarinex Reditabs; NeoClarityn; Claramax; Clarinex
• Synonyms: 8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-5H- benzo[5,6]cyclohepta[1,2,b]pyridine; Clarinex®; Desloratadine; 8-chloro-11-(piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine; 8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine; Aerius; Allex; Azomyr; Clarinex; NSC 675447; Neoclarityn; Opulis; Sch 34117; Claramax; Desloratidine; Descarboethoxyoratidine; Descarboethoxyloratadine; desloratadine; Desloratadine

Database IDs

• CAS Number: 100643-71-8
• MDL Number: MFCD00871949
• PubChem SID: 46507996; 160964305
• PubChem CID: 124087

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.74148434
• LogD (pH = 7.4): 1.6871009
• Log P: 3.968538
• Molar Refractivity: 101.0388 cm^3
• Polarizability: 35.36979 Å^3
• Polar Surface Area: 24.92 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.48
• LOG S: -4.9
• Solubility (Water): 3.95e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: >10 mg/mL; Ethyl Acetate; Hexane
• Apperance: Off-White to Beige Solid; powder
• Melting Point: 150-151°C
• Hydrophobicity(logP): 3.2

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Histamine Receptor
• Mechanism of Action: H1-antagonist

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Application(s): It is a drug used to treat allergies; Metab. of loratadine
• Empirical Formula (Hill Notation): C19H19ClN2

DETAILS

DrugBank - DB00967

• Drug Groups: approved; investigational
• Description: Desloratadine is a second generation, tricyclic antihistamine that which has a selective and peripheral H1-antagonist action. It is the active descarboethoxy metabolite of loratidine (a second generation histamine). Desloratidine has a long-lasting effect and does not cause drowsiness because it does not readily enter the central nervous system.
• Indication: For the relief of symptoms of seasonal allergic rhinitis, perennial (non-seasonal) allergic rhinitis. Desloratidine is also used for the sympomatic treatment of pruritus and urticaria (hives) associated with chronic idiopathic urticaria.
• Pharmacology: Desloratadine is a long-acting second-generation H₁-receptor antagonist which has a selective and peripheral H1-antagonist action. Histamine is a chemical that causes many of the signs that are part of allergic reactions, such as the swelling of tissues. Histamine is released from histamine-storing cells (mast cells) and attaches to other cells that have receptors for histamine. The attachment of the histamine to the receptors causes the cell to be "activated," releasing other chemicals which produce the effects that we associate with allergies. Desloratadine blocks one type of receptor for histamine (the H1 receptor) and thus prevents activation of cells by histamine. Unlike most other antihistamines, Desloratadine does not enter the brain from the blood and, therefore, does not cause drowsiness.
• Affected Organisms: Humans and other mammals
• Half Life: 50 hours
• Protein Binding: 82-87%
• Elimination: Desloratadine (a major metabolite of loratadine) is extensively metabolized to 3-hydroxydesloratadine, an active metabolite, which is subsequently glucuronidated. Approximately 87% of a 14C-desloratadine dose was equally recovered in urine and feces.
• References: Mann RD, Pearce GL, Dunn N, Shakir S: Sedation with "non-sedating" antihistamines: four prescription-event monitoring studies in general practice. BMJ. 2000 Apr 29;320(7243):1184-6. [Pubmed] ; Glass DJ, Harper AS: Assessing satisfaction with desloratadine and fexofenadine in allergy patients who report dissatisfaction with loratadine. BMC Fam Pract. 2003 Aug 13;4:10. Epub 2003 Aug 13. [Pubmed] ; See S: Desloratadine for allergic rhinitis. Am Fam Physician. 2003 Nov 15;68(10):2015-6. [Pubmed] ; Devillier P, Roche N, Faisy C: Clinical pharmacokinetics and pharmacodynamics of desloratadine, fexofenadine and levocetirizine : a comparative review. Clin Pharmacokinet. 2008;47(4):217-30. [Pubmed] ; Bachert C: A review of the efficacy of desloratadine, fexofenadine, and levocetirizine in the treatment of nasal congestion in patients with allergic rhinitis. Clin Ther. 2009 May;31(5):921-44. [Pubmed] ; DuBuske L: Desloratadine for chronic idiopathic urticaria: a review of clinical efficacy. Am J Clin Dermatol. 2007;8(5):271-83. [Pubmed] ; Bachert C, Maurer M: Safety and efficacy of desloratadine in subjects with seasonal allergic rhinitis or chronic urticaria: results of four postmarketing surveillance studies. Clin Drug Investig. 2010;30(2):109-22. doi: 10.2165/11530930-000000000-00000. [Pubmed] ; Simons FE, Prenner BM, Finn A Jr: Efficacy and safety of desloratadine in the treatment of perennial allergic rhinitis. J Allergy Clin Immunol. 2003 Mar;111(3):617-22. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - D1069

Biochem/physiol Actions
Desloratadine is a selective and nonsedating histamine H1 receptor antagonist, an active metabolite of loratadine (Claritin), used to relieve hay fever and allergy symptoms with less drowsiness than other antihistamines; does not significantly inhibits cardiac K+ channels at clinically achievable blood levels. Free from antimuscarinic/anticholinergic effects.
Legal Information
Clarinex is a registered trademark of Schering Corp.

Toronto Research Chemicals - D290250

Nonsedating-type histamine H1-receptor antagonist. An active metabolite of Loratadine. Also inhibits generation and release of inflammatory mediators from basophils and mast cells.An impurity arising in the synthesis of Rupatadine (R701650).

REFERENCES

• Mann RD, Pearce GL, Dunn N, Shakir S: Sedation with "non-sedating" antihistamines: four prescription-event monitoring studies in general practice. BMJ. 2000 Apr 29;320(7243):1184-6. Pubmed
• Glass DJ, Harper AS: Assessing satisfaction with desloratadine and fexofenadine in allergy patients who report dissatisfaction with loratadine. BMC Fam Pract. 2003 Aug 13;4:10. Epub 2003 Aug 13. Pubmed
• Devillier P, Roche N, Faisy C: Clinical pharmacokinetics and pharmacodynamics of desloratadine, fexofenadine and levocetirizine : a comparative review. Clin Pharmacokinet. 2008;47(4):217-30. Pubmed
• Bachert C: A review of the efficacy of desloratadine, fexofenadine, and levocetirizine in the treatment of nasal congestion in patients with allergic rhinitis. Clin Ther. 2009 May;31(5):921-44. Pubmed
• DuBuske L: Desloratadine for chronic idiopathic urticaria: a review of clinical efficacy. Am J Clin Dermatol. 2007;8(5):271-83. Pubmed
• Bachert C, Maurer M: Safety and efficacy of desloratadine in subjects with seasonal allergic rhinitis or chronic urticaria: results of four postmarketing surveillance studies. Clin Drug Investig. 2010;30(2):109-22. doi: 10.2165/11530930-000000000-00000. Pubmed
• Simons FE, Prenner BM, Finn A Jr: Efficacy and safety of desloratadine in the treatment of perennial allergic rhinitis. J Allergy Clin Immunol. 2003 Mar;111(3):617-22. Pubmed
• See S: Desloratadine for allergic rhinitis. Am Fam Physician. 2003 Nov 15;68(10):2015-6. Pubmed
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