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Lisuride

Synopsis, Chemistry

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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

Lisuride

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 Formula	C₂₀H₂₆N₄O
Molecular Weight	338.4 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Exact Mass	338.21066147 g/mol
Monoisotopic Mass	338.21066147 g/mol
Topological Polar Surface Area	51.4 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	544
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.