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Chemistry

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Also known as: 191217-81-9, Mirapex, (s)-n6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine dihydrochloride hydrate, Pramipexole 2hcl monohydrate, Pramipexole hydrochloride, Sifrol
Molecular Formula
C10H21Cl2N3OS
Molecular Weight
302.3  g/mol
InChI Key
APVQOOKHDZVJEX-QTPLPEIMSA-N
FDA UNII
3D867NP06J

Pramipexole Dihydrochloride
A benzothiazole derivative and dopamine agonist with antioxidant properties that is used in the treatment of PARKINSON DISEASE and RESTLESS LEGS SYNDROME.
1 2D Structure

Pramipexole Dihydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6S)-6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;hydrate;dihydrochloride
2.1.2 InChI
InChI=1S/C10H17N3S.2ClH.H2O/c1-2-5-12-7-3-4-8-9(6-7)14-10(11)13-8;;;/h7,12H,2-6H2,1H3,(H2,11,13);2*1H;1H2/t7-;;;/m0.../s1
2.1.3 InChI Key
APVQOOKHDZVJEX-QTPLPEIMSA-N
2.1.4 Canonical SMILES
CCCNC1CCC2=C(C1)SC(=N2)N.O.Cl.Cl
2.1.5 Isomeric SMILES
CCCN[C@H]1CCC2=C(C1)SC(=N2)N.O.Cl.Cl
2.2 Other Identifiers
2.2.1 UNII
3D867NP06J
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2 Amino 6 Propylaminotetrahydrobenzothiazole

2. 2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole

3. 2-amino-6-propylaminotetrahydrobenzothiazole

4. 4,5,6,7-tetrahydro-n6-propyl-2,6-benzothiazole-diamine

5. 6,7-tetrahydro-n6-propyl-2,6-benzothiazolediamine Dihydrochloride Monohydrate

6. Dexpramipexole

7. Kns 760704

8. Kns-760704

9. Kns760704

10. Mirapex

11. Pramipexol

12. Pramipexol Dihydrobromide, (+-)-isomer

13. Pramipexol Dihydrochloride, (s)-isomer

14. Pramipexol, (+-)-isomer

15. Pramipexol, (r)-isomer

16. Pramipexole

17. Pramipexole Dihydrochloride

18. Pramipexole Dihydrochloride Anhydrous

19. Pramipexole Hydrochloride Monohydrate

20. Sifrol

21. Snd 919

22. Snd 919cl2x

23. Snd-919

24. Snd-919cl2x

25. Snd919cl2x

2.3.2 Depositor-Supplied Synonyms

1. 191217-81-9

2. Mirapex

3. (s)-n6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine Dihydrochloride Hydrate

4. Pramipexole 2hcl Monohydrate

5. Pramipexole Hydrochloride

6. Sifrol

7. Daquiran

8. Pramipexole Hydrochloride Hydrate

9. Pramipexole Teva

10. Pramipexole Accord

11. Snd919cl2y

12. Bi-sifrol

13. Pnu-98528e

14. 191712-81-9

15. (s)-2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole Dihydrochloride Monohydrate

16. Pramipexole Dihydrochloride [usan]

17. Chebi:51147

18. 3d867np06j

19. Oprymea

20. Pramipexole (dihydrochloride Hydrate)

21. Snd-919cl2y

22. (6s)-6-n-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;hydrate;dihydrochloride

23. Pramipexole Hydrochloride Hydrate (jan)

24. Pramipexole Dihydrochloride Anhydrous

25. Pramipexole Hydrochloride Hydrate [jan]

26. Pramipexole Hcl Hydrate

27. Unii-3d867np06j

28. Pramipexole Dihydrochloride Hydrate

29. Pramipexole Hydrate Dihydrochloride

30. Pnu 98528e

31. Mirapex (tn)

32. Pramipexole Dihydrochloride [usan:usp]

33. Dsstox_cid_24227

34. Dsstox_rid_80129

35. Dsstox_gsid_44227

36. Chembl3182733

37. Dtxsid1044227

38. Hy-b0410a

39. Pramipexole Dihydrochloride (usp)

40. Pramipexole Hydrochloride Monohydrate

41. Tox21_302316

42. Mfcd02183927

43. S2011

44. Akos015917338

45. Ccg-267486

46. Ks-1308

47. 2,6-benzothiazolediamine, 4,5,6,7-tetrahydro-n6-propyl-, Dihydrochloride, Monohydrate, (6s)-

48. Ncgc00255978-01

49. Pramipexole Hydrochloride [mart.]

50. 112gi013

51. Bp162212

52. Bp164285

53. Pramipexole Dihydrochloride [vandf]

54. Cas-191217-81-9

55. Cs-0013154

56. Sw197453-5

57. (s)-pramipexole 2hcl Monohydrate - Ep Grade

58. Pramipexole Dihydrochloride Monohydrate- Bio-x

59. D00559

60. T72003

61. Pramipexole Dihydrochloride [orange Book]

62. A846638

63. Pramipexole Dihydrochloride [usp Monograph]

64. J-012354

65. Pramipexole Dihydrochloride Monohydrate [mi]

66. Q27888021

67. Pramipexole Dihydrochloride Monohydrate [ema Epar]

68. Pramipexole Dihydrochloride Monohydrate [usp-rs]

69. Pramipexole Dihydrochloride Monohydrate [who-dd]

70. Pramipexole Dihydrochloride Monohydrate [ep Monograph]

71. (6s)-n(6)-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine Dihydrochloride Hydrate

72. (s)-2-amino-4,5,6,7-tetrahydro-6(propylamino)benzothiazole Dihydrochloride Monohydrate

73. (s)-n6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine 2hcl Hydrate

74. (s)-n6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diaminedihydrochloridehydrate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 302.3 g/mol
Molecular Formula C10H21Cl2N3OS
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass301.0782389 g/mol
Monoisotopic Mass301.0782389 g/mol
Topological Polar Surface Area80.2 Ų
Heavy Atom Count17
Formal Charge0
Complexity188
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count4
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameMirapex
PubMed HealthPramipexole (By mouth)
Drug ClassesAntiparkinsonian
Drug LabelMIRAPEX tablets contain pramipexole, a nonergot dopamine agonist. The chemical name of pramipexole dihydrochloride is (S)-2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole dihydrochloride monohydrate. Its empirical formula is C10 H17 N3 S 2...
Active IngredientPramipexole dihydrochloride
Dosage FormTablet
RouteOral
Strength0.5mg; 1mg; 0.25mg; 0.75mg; 1.5mg; 0.125mg
Market StatusPrescription
CompanyBoehringer Ingelheim

2 of 4  
Drug NamePramipexole dihydrochloride
Drug LabelMIRAPEX tablets contain pramipexole, a nonergot dopamine agonist. The chemical name of pramipexole dihydrochloride is (S)-2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole dihydrochloride monohydrate. Its empirical formula is C10 H17 N3 S 2...
Active IngredientPramipexole dihydrochloride
Dosage FormTablet, extended release; Tablet
RouteOral
Strength0.5mg; 1mg; 0.25mg; 0.75mg; 3.75mg; 1.5mg; 4.5mg; 2.25mg; 0.375mg; 3mg; 0.125mg
Market StatusPrescription
CompanyAnchen Pharms; Alembic; Breckenridge Pharm; Apotex; Aurobindo Pharma; Sun Pharm Inds; Torrent Pharms; Sandoz; Actavis Grp Ptc; Watson Labs; Strides Pharma; Glenmark Generics; Teva Pharms; Macleods Pharms; Zydus Pharms Usa; Mylan; Barr

3 of 4  
Drug NameMirapex
PubMed HealthPramipexole (By mouth)
Drug ClassesAntiparkinsonian
Drug LabelMIRAPEX tablets contain pramipexole, a nonergot dopamine agonist. The chemical name of pramipexole dihydrochloride is (S)-2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole dihydrochloride monohydrate. Its empirical formula is C10 H17 N3 S 2...
Active IngredientPramipexole dihydrochloride
Dosage FormTablet
RouteOral
Strength0.5mg; 1mg; 0.25mg; 0.75mg; 1.5mg; 0.125mg
Market StatusPrescription
CompanyBoehringer Ingelheim

4 of 4  
Drug NamePramipexole dihydrochloride
Drug LabelMIRAPEX tablets contain pramipexole, a nonergot dopamine agonist. The chemical name of pramipexole dihydrochloride is (S)-2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole dihydrochloride monohydrate. Its empirical formula is C10 H17 N3 S 2...
Active IngredientPramipexole dihydrochloride
Dosage FormTablet, extended release; Tablet
RouteOral
Strength0.5mg; 1mg; 0.25mg; 0.75mg; 3.75mg; 1.5mg; 4.5mg; 2.25mg; 0.375mg; 3mg; 0.125mg
Market StatusPrescription
CompanyAnchen Pharms; Alembic; Breckenridge Pharm; Apotex; Aurobindo Pharma; Sun Pharm Inds; Torrent Pharms; Sandoz; Actavis Grp Ptc; Watson Labs; Strides Pharma; Glenmark Generics; Teva Pharms; Macleods Pharms; Zydus Pharms Usa; Mylan; Barr

4.2 Drug Indication

Sifrol is indicated for treatment of the signs and symptoms of idiopathic Parkinson's disease, alone (without levodopa) or in combination with levodopa, i. e. over the course of the disease, though to late stages when the effect of levodopa wears off or becomes inconsistent and fluctuations of the therapeutic effect occur (end-of-dose or 'on-off' fluctuations).

Sifrol is indicated for symptomatic treatment of moderate to severe idiopathic restless-legs syndrome in dosages up to 0. 54 mg of base (0. 75 mg of salt).


Mirapexin is indicated for treatment of the signs and symptoms of idiopathic Parkinson's disease, alone (without levodopa) or in combination with levodopa, i. e. over the course of the disease, through to late stages when the effect of levodopa wears off or becomes inconsistent and fluctuations of the therapeutic effect occur (end-of-dose or 'on-off' fluctuations).

Mirapexin is indicated for symptomatic treatment of moderate to severe idiopathic restless-legs syndrome in dosages up to 0. 54 mg of base (0. 75 mg of salt).


Oprymea is indicated for treatment of the signs and symptoms of idiopathic Parkinson's disease, alone (without levodopa) or in combination with levodopa, i. e. over the course of the disease, through to late stages when the effect of levodopa wears off or becomes inconsistent and fluctuations of the therapeutic effect occur (end of dose or "on off" fluctuations).

Oprymea is indicated in adults for symptomatic treatment of moderate to severe idiopathic Restless Legs Syndrome in doses up to 0. 54 mg of base (0. 75 mg of salt) (see section 4. 2).


Pramipexole Teva is indicated for treatment of the signs and symptoms of idiopathic Parkinson's disease, alone (without levodopa) or in combination with levodopa, i. e. over the course of the disease, through to late stages when the effect of levodopa wears off or becomes inconsistent and fluctuations of the therapeutic effect occur (end-of-dose or 'on-off' fluctuations).

Pramipexole Teva is indicated in adults for symptomatic treatment of moderate to severe idiopathic Restless Legs Syndrome in doses up to 0. 54 mg of base (0. 75 mg of salt) (see section 4. 2).


Pramipexole Accord is indicated in adults for treatment of the signs and symptoms of idiopathic Parkinson's disease, alone (without levodopa) or in combination with levodopa, i. e. over the course of the disease, through to late stages when the effect of levodopa wears off or becomes inconsistent and fluctuations of the therapeutic effect occur (end-of-dose or 'on-off' fluctuations).


DAQUIRAN tablets are indicated for treatment of the signs and symptoms of advanced idiopathic Parkinson's disease in combination with levodopa, i. e. over the course of the disease, when the effect of levodopa wears off or becomes inconsistent and fluctuations of the therapeutic effect occur (end of dose or "on off" fluctuations).


Combined vocal and multiple motor tic disorder (de la Tourette), Restless Legs Syndrome


Combined vocal and multiple motor tic disorder (de la Tourette), Restless Legs Syndrome


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)


Dopamine Agonists

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


5.2 ATC Code

N04BC05


N04BC05


N04BC05


N04BC05


N04BC05


N04BC05


API Reference Price

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22-Jan-2021
31-Aug-2024
KGS
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DOSAGE - TABLET;ORAL - 0.125MG **Federal Regi...DOSAGE - TABLET;ORAL - 0.125MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20667

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DOSAGE - TABLET;ORAL - 0.25MG **Federal Regis...DOSAGE - TABLET;ORAL - 0.25MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20667

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DOSAGE - TABLET;ORAL - 0.5MG **Federal Regist...DOSAGE - TABLET;ORAL - 0.5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20667

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DOSAGE - TABLET;ORAL - 0.75MG **Federal Regis...DOSAGE - TABLET;ORAL - 0.75MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20667

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DOSAGE - TABLET;ORAL - 1.5MG **Federal Regist...DOSAGE - TABLET;ORAL - 1.5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20667

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DOSAGE - TABLET;ORAL - 1MG **Federal Register...DOSAGE - TABLET;ORAL - 1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20667

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