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    Levocetirizine Dihydrochloride

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 130018-87-0, Xyzal, Xusal, (r)-cetirizine dihydrochloride, Levocetirizine hcl, Levocetirizine dihydrochloride [usan]
    Molecular Formula
    C21H27Cl3N2O3
    Molecular Weight
    461.8  g/mol
    InChI Key
    PGLIUCLTXOYQMV-GHVWMZMZSA-N
    FDA UNII
    SOD6A38AGA
    Levocetirizine Dihydrochloride is the dihydrochloride salt form of the active levorotatory enantiomer of cetirizine, levocetirizine; a third generation, non-sedating, selective histamine H1 receptor antagonist, with antihistamine, anti-inflammatory and potential anti-angiogenic activities. Levocetirizine competes with endogenous histamine for binding at peripheral H1-receptor sites on the effector cell surface. This prevents the negative symptoms associated with histamine release and an allergic reaction. In addition, as histamine plays an important role in angiogenesis during an allergic inflammatory reaction, blocking the action of histamine may modulate the expression of proangiogenic factors and thus may prevent angiogenesis. As a third-generation histamine H1 receptor antagonist, levocetirizine has fewer side effects than most second-generation antihistamines.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[2-[4-[(R)-(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic acid;dihydrochloride
    2.1.2 InChI
    InChI=1S/C21H25ClN2O3.2ClH/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);2*1H/t21-;;/m1../s1
    2.1.3 InChI Key
    PGLIUCLTXOYQMV-GHVWMZMZSA-N
    2.1.4 Canonical SMILES
    C1CN(CCN1CCOCC(=O)O)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl.Cl.Cl
    2.1.5 Isomeric SMILES
    C1CN(CCN1CCOCC(=O)O)[C@H](C2=CC=CC=C2)C3=CC=C(C=C3)Cl.Cl.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    SOD6A38AGA
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2-(4-((r)-(4-chlorophenyl)phenylmethyl)piperazin-1-yl)ethoxy)acetic Acid Dihydrochloride

    2. (2-(4-((r)-p-chloro-alpha-phenylbenzyl)-1-piperazinyl)ethoxy)acetic Acid

    3. Acetic Acid, (2-(4-((r)-(4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-

    4. Acetic Acid, (2-(4-((r)-(4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-, Dihydrochloride

    5. Cetirizine (r)-form Dihydrochloride

    6. Levocetirizine

    7. Levocetirizine Hydrochloride

    8. Levocetrizine

    9. Ucb-28556

    10. Xusal

    11. Xyzal

    2.3.2 Depositor-Supplied Synonyms

    1. 130018-87-0

    2. Xyzal

    3. Xusal

    4. (r)-cetirizine Dihydrochloride

    5. Levocetirizine Hcl

    6. Levocetirizine Dihydrochloride [usan]

    7. Cetirizine (r)-form Dihydrochloride

    8. Ucb-28556

    9. Sod6a38aga

    10. Ucb 28556

    11. (2-(4-((r)-(4-chlorophenyl)phenylmethyl)piperazin-1-yl)ethoxy)acetic Acid Dihydrochloride

    12. (r)-2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetic Acid Dihydrochloride

    13. Acetic Acid, (2-(4-((r)-(4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-, Dihydrochloride

    14. Nsc-758898

    15. Levocetirizine Hydrochloride (jan)

    16. (-)-cetirizine Dihydrochloride

    17. 2-[2-[4-[(r)-(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic Acid;dihydrochloride

    18. 2-[2-[4-[(r)-(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic Acid Dihydrochloride

    19. Levocetirizine (dihydrochloride)

    20. Levocetirizine Hydrochloride [jan]

    21. Levocetirizine 2hcl

    22. Unii-sod6a38aga

    23. Levocetirizine Dihcl

    24. Mfcd07366507

    25. Xyzal Allergy 24hr

    26. Xyzal (tn)

    27. Levocetirizinedihydrochloride

    28. Schembl144375

    29. Chembl1201190

    30. Levocetirizine Hydrochloride,(s)

    31. Dtxsid30926567

    32. Bcp21544

    33. Ac-549

    34. Levocetirizine Dihydrochloride (usp)

    35. S4849

    36. Akos015994681

    37. Ccg-269359

    38. Cs-w011557

    39. Hy-w010841

    40. Ks-1177

    41. Nsc 758898

    42. [2-[4-[(r)-(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic Acid 2hcl

    43. 2-[2-[4-[(r)-(4-chlorophenyl)phenylmethyl]piperazin-1-yl]ethoxy]acetic Acid Dihydrochloride

    44. Levocetirizine Hydrochloride [mart.]

    45. L0264

    46. Levocetirizine Dihydrochloride [vandf]

    47. Levocetirizine(r)-cetirizine (hydrochloride)

    48. D08118

    49. Levocetirizine Dihydrochloride [usp-rs]

    50. Levocetirizine Dihydrochloride [who-dd]

    51. Levocetirizine Dihydrochloride, >=98% (hplc)

    52. Cetirizine (r)-form Dihydrochloride [mi]

    53. 018l870

    54. Levocetirizine Dihydrochloride [orange Book]

    55. Levocetirizine Dihydrochloride [usp Monograph]

    56. Q27289313

    57. [2-[4-[(r)-(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic Acid Dihydrochloride

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 461.8 g/mol
    Molecular Formula C21H27Cl3N2O3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count8
    Exact Mass460.108726 g/mol
    Monoisotopic Mass460.108726 g/mol
    Topological Polar Surface Area53 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity443
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameLevocetirizine dihydrochloride
    Drug LabelLevocetirizine dihydrochloride, the active component of levocetirizine dihydrochloride tablets, is an orally active H1-receptor antagonist. The chemical name is R-(+)-2-[2-[4-[(4-chlorophenyl) phenyl methyl] piperazin-1-yl] ethoxy] acetic acid dihydr...
    Active IngredientLevocetirizine dihydrochloride
    Dosage FormTablet; Solution
    RouteOral
    Strength2.5mg/5ml; 5mg
    Market StatusPrescription
    CompanySynthon Pharms; Apotex; Hetero Labs Ltd Iii; Sciegen Pharms; Taro Pharm Inds; Sun Pharma Global; Glenmark Generics; Teva Pharms; Micro Labs Ltd India; Dr Reddys Labs; L Perrigo

    2 of 4  
    Drug NameXyzal
    PubMed HealthLevocetirizine (By mouth)
    Drug ClassesRespiratory Agent
    Drug LabelLevocetirizine dihydrochloride, the active component of XYZAL tablets and oral solution, is an orally active H1receptor antagonist. The chemical name is (R)-[2-[4-[(4-chlorophenyl) phenylmethyl]-1-piperazinyl] ethoxy] acetic acid dihydrochloride....
    Active IngredientLevocetirizine dihydrochloride
    Dosage FormTablet; Solution
    RouteOral
    Strength2.5mg/5ml; 5mg
    Market StatusPrescription
    CompanyUcb

    3 of 4  
    Drug NameLevocetirizine dihydrochloride
    Drug LabelLevocetirizine dihydrochloride, the active component of levocetirizine dihydrochloride tablets, is an orally active H1-receptor antagonist. The chemical name is R-(+)-2-[2-[4-[(4-chlorophenyl) phenyl methyl] piperazin-1-yl] ethoxy] acetic acid dihydr...
    Active IngredientLevocetirizine dihydrochloride
    Dosage FormTablet; Solution
    RouteOral
    Strength2.5mg/5ml; 5mg
    Market StatusPrescription
    CompanySynthon Pharms; Apotex; Hetero Labs Ltd Iii; Sciegen Pharms; Taro Pharm Inds; Sun Pharma Global; Glenmark Generics; Teva Pharms; Micro Labs Ltd India; Dr Reddys Labs; L Perrigo

    4 of 4  
    Drug NameXyzal
    PubMed HealthLevocetirizine (By mouth)
    Drug ClassesRespiratory Agent
    Drug LabelLevocetirizine dihydrochloride, the active component of XYZAL tablets and oral solution, is an orally active H1receptor antagonist. The chemical name is (R)-[2-[4-[(4-chlorophenyl) phenylmethyl]-1-piperazinyl] ethoxy] acetic acid dihydrochloride....
    Active IngredientLevocetirizine dihydrochloride
    Dosage FormTablet; Solution
    RouteOral
    Strength2.5mg/5ml; 5mg
    Market StatusPrescription
    CompanyUcb

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Histamine H1 Antagonists, Non-Sedating

    A class of non-sedating drugs that bind to but do not activate histamine receptors (DRUG INVERSE AGONISM), thereby blocking the actions of histamine or histamine agonists. These antihistamines represent a heterogenous group of compounds with differing chemical structures, adverse effects, distribution, and metabolism. Compared to the early (first generation) antihistamines, these non-sedating antihistamines have greater receptor specificity, lower penetration of BLOOD-BRAIN BARRIER, and are less likely to cause drowsiness or psychomotor impairment. (See all compounds classified as Histamine H1 Antagonists, Non-Sedating.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Histamine-1 Receptor Antagonist [EPC]; Histamine H1 Receptor Antagonists [MoA]