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    Lisuride

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
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    2D Structure
    Also known as: Lysuride, 18016-80-3, Lisuride [inn], Lisurida, Lisuridum, Lisuride maleate
    Molecular Formula
    C20H26N4O
    Molecular Weight
    338.4  g/mol
    InChI Key
    BKRGVLQUQGGVSM-KBXCAEBGSA-N
    FDA UNII
    E0QN3D755O
    An ergot derivative that acts as an agonist at dopamine D2 receptors (DOPAMINE AGONISTS). It may also act as an antagonist at dopamine D1 receptors, and as an agonist at some serotonin receptors (SEROTONIN RECEPTOR AGONISTS).
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[(6aR,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-1,1-diethylurea
    2.1.2 InChI
    InChI=1S/C20H26N4O/c1-4-24(5-2)20(25)22-14-10-16-15-7-6-8-17-19(15)13(11-21-17)9-18(16)23(3)12-14/h6-8,10-11,14,18,21H,4-5,9,12H2,1-3H3,(H,22,25)/t14-,18+/m0/s1
    2.1.3 InChI Key
    BKRGVLQUQGGVSM-KBXCAEBGSA-N
    2.1.4 Canonical SMILES
    CCN(CC)C(=O)NC1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C
    2.1.5 Isomeric SMILES
    CCN(CC)C(=O)N[C@@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
    2.2 Other Identifiers
    2.2.1 UNII
    E0QN3D755O
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Arolac

    2. Carbamide, Methylergol

    3. Cuvalit

    4. Dopergin

    5. Dopergine

    6. Hydrochloride, Lisuride

    7. Hydrogen Maleate, Lysuride

    8. Lisuride Hydrochloride

    9. Lisuride Maleate

    10. Lisuride Maleate (1:1)

    11. Lisuride Maleate, (8beta)-isomer

    12. Lisuride Mesylate

    13. Lisuride Phosphate (1:1)

    14. Lisuride, (8alpha)-(+-)-isomer

    15. Lysenyl

    16. Lysurid

    17. Lysuride Hydrogen Maleate

    18. Maleate, Lisuride

    19. Mesylate, Lisuride

    20. Methylergol Carbamide

    21. Revanil

    2.3.2 Depositor-Supplied Synonyms

    1. Lysuride

    2. 18016-80-3

    3. Lisuride [inn]

    4. Lisurida

    5. Lisuridum

    6. Lisuride Maleate

    7. Lisuride (inn)

    8. 140387-89-9

    9. Lisuride (s)(-)

    10. N'-((8alpha)-9,10-didehydro-6-methylergolin-8-yl)-n,n-diethylurea

    11. S-(-)-lisuride

    12. Chembl157138

    13. E0qn3d755o

    14. Chebi:51164

    15. 1,1-diethyl-3-[(8alpha)-6-methyl-9,10-didehydroergolin-8-yl]urea

    16. 18016-80-3 (free Base)

    17. Lisuridum [inn-latin]

    18. Lysuride Maleate

    19. Lisurida [inn-spanish]

    20. N,n-diethyl-n'-[(8alpha)-6-methyl-9,10-didehydroergolin-8-yl]urea

    21. Dopergin

    22. Dl-lisuride

    23. 1,1-diethyl-3-((6ar,9s)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)urea

    24. 3-[(6ar,9s)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinolin-9-yl]-1,1-diethylurea

    25. 3,3-diethyl-1-[(4s,7r)-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaen-4-yl]urea

    26. Lisuride [inn:ban]

    27. Einecs 241-925-1

    28. Unii-e0qn3d755o

    29. (+)-lisuride

    30. H8g

    31. Lisuride, (s)

    32. Prestwick_525

    33. 3-(9,10-didehydro-6-methylergolin-8alpha-yl)-1,1-diethylurea

    34. Lisuride [mi]

    35. Prestwick0_000106

    36. Prestwick1_000106

    37. Prestwick2_000106

    38. Prestwick3_000106

    39. Urea, N'-((8alpha)-9,10-didehydro-6-methylergolin-8-yl)-n,n-diethyl-

    40. Gtpl43

    41. Lisuride [who-dd]

    42. Lopac0_000751

    43. Schembl43950

    44. Bspbio_000092

    45. Spbio_002031

    46. Bpbio1_000102

    47. Dtxsid3023217

    48. Dtxsid30274075

    49. Hms1568e14

    50. Zinc3831001

    51. Bdbm50056445

    52. Ccg-204836

    53. Db00589

    54. Ncgc00179663-02

    55. Hy-12713

    56. Cs-0012290

    57. D08132

    58. Q424446

    59. 1,1-diethyl-3-(9,10-didehydro-6-methyl-8alpha-ergolinyl)urea

    60. 3-(9,10-didehydro-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

    61. 3-(9,10-didehydro-6-methylergolin-8.alpha.-yl)-1,1-diethylurea

    62. N''-((8alpha)-9,10-didehydro-6-methylergolin-8-yl)-n,n-diethylurea

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 338.4 g/mol
    Molecular Formula C20H26N4O
    XLogP32.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count3
    Exact Mass338.21066147 g/mol
    Monoisotopic Mass338.21066147 g/mol
    Topological Polar Surface Area51.4 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity544
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the management of Parkinson's Disease

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    There is evidence that lisuride lowers prolactin levels and, in low doses, prevents migraine attacks.

    5.2 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.)

    Antiparkinson Agents

    Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists. (See all compounds classified as Antiparkinson Agents.)

    Dopamine Agonists

    Drugs that bind to and activate dopamine receptors. (See all compounds classified as Dopamine Agonists.)

    5.3 ATC Code

    G - Genito urinary system and sex hormones

    G02 - Other gynecologicals

    G02C - Other gynecologicals

    G02CB - Prolactine inhibitors

    G02CB02 - Lisuride

    N - Nervous system

    N02 - Analgesics

    N02C - Antimigraine preparations

    N02CA - Ergot alkaloids

    N02CA07 - Lisuride

    5.4 Mechanism of Action

    Lisuride is an anti-Parkinson drug chemically related to the dopaminergic ergoline Parkinson's drugs. Lisuride binds to the 5-HT(1A) and 5-HT(2A/2C) receptors. It is also thought to bind to the dopamine receptor and to act as a dopamine agonist. Evidence has also emerged that Lisuride also binds to the Histamine H1 receptor.