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    Chemistry

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    Also known as: 177834-92-3, Eletriptan hbr, Relpax, Eletriptan hydrobromide [usan], Eletriptan (hydrobromide), (r)-3-((1-methylpyrrolidin-2-yl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole hydrobromide
    Molecular Formula
    C22H27BrN2O2S
    Molecular Weight
    463.4  g/mol
    InChI Key
    UTINOWOSWSPFLJ-FSRHSHDFSA-N
    FDA UNII
    M41W832TA3
    Eletriptan Hydrobromide
    Eletriptan Hydrobromide is a triptan with specific affinity for the 5-hydroxytriptamine1B/1D receptor. Eletriptan hydrobromide binds to and acts at serotonin 5-HT1B receptors located on intracranial blood vessels which leads to vasoconstriction. This drug may also exerts its effects by binding to and activating 5-HT 1D receptors on sensory nerve endings in the trigeminal system, which results in the inhibition of pro-inflammatory neuropeptide release. Eletriptan hydrobromide is used to relieve pain or symptoms associated with migraine headaches.
    1 2D Structure

    Eletriptan Hydrobromide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[2-(benzenesulfonyl)ethyl]-3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-1H-indole;hydrobromide
    2.1.2 InChI
    InChI=1S/C22H26N2O2S.BrH/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20;/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3;1H/t19-;/m1./s1
    2.1.3 InChI Key
    UTINOWOSWSPFLJ-FSRHSHDFSA-N
    2.1.4 Canonical SMILES
    CN1CCCC1CC2=CNC3=C2C=C(C=C3)CCS(=O)(=O)C4=CC=CC=C4.Br
    2.1.5 Isomeric SMILES
    CN1CCC[C@@H]1CC2=CNC3=C2C=C(C=C3)CCS(=O)(=O)C4=CC=CC=C4.Br
    2.2 Other Identifiers
    2.2.1 UNII
    M41W832TA3
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (r)-3-((1-methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole

    2. (r)-3-((1-methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole Monohydrobromide

    3. 3-(1-methyl-2-pyrrolidinylmethyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole Hydrobromide

    4. Eletriptan

    5. Relpax

    6. Uk 166,044

    7. Uk 166044

    8. Uk-116,044-04

    9. Uk-116044-04

    10. Uk-166,044

    11. Uk-166044

    2.3.2 Depositor-Supplied Synonyms

    1. 177834-92-3

    2. Eletriptan Hbr

    3. Relpax

    4. Eletriptan Hydrobromide [usan]

    5. Eletriptan (hydrobromide)

    6. (r)-3-((1-methylpyrrolidin-2-yl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole Hydrobromide

    7. Eletriptan Monohydrobromide

    8. Uk 116044-04

    9. Chebi:61176

    10. M41w832ta3

    11. Uk-116,044-04

    12. (r)-3-((1-methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1h-indole Monohydrobromide

    13. 5-[2-(benzenesulfonyl)ethyl]-3-[[(2r)-1-methylpyrrolidin-2-yl]methyl]-1h-indole;hydrobromide

    14. Nsc-759258

    15. 3-(((r)-1-methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)indole, Monohydrobromide

    16. 5-[2-(phenylsulfonyl)ethyl]-3-[(2r)-pyrrolidin-2-ylmethyl]-1h-indole Hydrobromide

    17. C22h26n2o2s.hbr

    18. Unii-m41w832ta3

    19. Relpax (tn)

    20. Schembl317370

    21. Chembl1201003

    22. Dtxsid001016113

    23. Hy-a0010

    24. Eletriptan Hydrobromide (jan/usan)

    25. Eletriptan Hydrobromide [mi]

    26. Tox21_500408

    27. Eletriptan Hydrobromide [jan]

    28. Mfcd08141806

    29. S3180

    30. Akos024262728

    31. Ac-3398

    32. Bcp9000640

    33. Ccg-221712

    34. Cs-0379

    35. Eletriptan Hydrobromide [mart.]

    36. Nsc 759258

    37. 3-[[(2r)-1-methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-1h-indole Hydrobromide

    38. Eletriptan Hydrobromide [usp-rs]

    39. Eletriptan Hydrobromide [who-dd]

    40. Ncgc00261093-01

    41. Bs-42146

    42. Eletriptan Hydrobromide, >=98% (hplc)

    43. Eletriptan Hydrobromide [orange Book]

    44. Sw220149-1

    45. D01973

    46. J-011323

    47. J-520433

    48. Q27130865

    49. 3-(n-methyl-2(r)-pyrrolidinyl Methyl)-5-[2-(phenyl Sulfonyl)ethyl]-1h-indole Hydrobromide

    50. 3-(n-methyl-2(r)-pyrrolidinylmethyl)-5-(2-phenylsulphonylethly)-1h-indole Hydrobromide

    51. 3-(n-methyl-2(r)-pyrrolidinylmethyl)-5-(2-phenylsulphonylethyl)-1h-indole Hydrobromide

    52. 3-(n-methyl-2(r)-pyrrolidinylmethyl)-5-[2-(phenyl Sulfonyl)ethyl]-1h-indole Hydrobromide

    53. 3-{[1-methylpyrrolidin-2(r)-yl]methyl}-5-(2-phenylsulphonylethyl)-1h-indole Hydrobromide

    54. (r)-3-[(1-methyl-2-pyrrolidinyl) Methyl]-5-[2-(phenylsulfonyl) Ethyl]-1h-indole Monohydrobromide

    55. 1h-indole, 3-(((2r)-1-methyl-2-pyrrolidinyl))methyl)-5-(2-(phenylsulfonyl)ethyl)-, Monohydrobromide

    56. 1h-indole, 3-[[(2r)-1-methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-, Hydrobromide (1:1)

    57. 3-[[(2r)-1-methyl-2-pyrrolidinyl]me Thyl]-5-[2-(phenylsulfonyl)ethyl]-1h-indole Hydrobromide

    58. 5-[2-(benzenesulfonyl)ethyl]-3-[[(2r)-1-methylpyrrolidin-2-yl]methyl]-1h-indol-1-ium;bromide

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 463.4 g/mol
    Molecular Formula C22H27BrN2O2S
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count6
    Exact Mass462.09766 g/mol
    Monoisotopic Mass462.09766 g/mol
    Topological Polar Surface Area61.6 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity582
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameEletriptan hydrobromide
    Drug LabelRELPAX (eletriptan) Tablets contain eletriptan hydrobromide, which is a selective 5-hydroxytryptamine 1B/1D (5-HT1B/1D) receptor agonist. Eletriptan is chemically designated as (R)-3-[(1-Methyl-2-pyrrolidinyl)methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-...
    Active IngredientEletriptan hydrobromide
    Dosage FormTablet
    Routeoral
    Strengtheq 40mg base; eq 20mg base; 40mg; 20mg
    Market StatusTentative Approval
    CompanyApotex; Teva Pharms Usa

    2 of 2  
    Drug NameEletriptan hydrobromide
    Drug LabelRELPAX (eletriptan) Tablets contain eletriptan hydrobromide, which is a selective 5-hydroxytryptamine 1B/1D (5-HT1B/1D) receptor agonist. Eletriptan is chemically designated as (R)-3-[(1-Methyl-2-pyrrolidinyl)methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-...
    Active IngredientEletriptan hydrobromide
    Dosage FormTablet
    Routeoral
    Strengtheq 40mg base; eq 20mg base; 40mg; 20mg
    Market StatusTentative Approval
    CompanyApotex; Teva Pharms Usa

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Serotonin Receptor Agonists

    Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS. (See all compounds classified as Serotonin Receptor Agonists.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Serotonin 1d Receptor Agonists [MoA]; Serotonin-1b and Serotonin-1d Receptor Agonist [EPC]; Serotonin 1b Receptor Agonists [MoA]

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    02-Jan-2021
    28-Sep-2024
    KGS
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