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Chemistry

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Also known as: 123441-03-2, Exelon, Ena 713 free base, Prometax, Rivastigmine teva, Nimvastid
Molecular Formula
C14H22N2O2
Molecular Weight
250.34  g/mol
InChI Key
XSVMFMHYUFZWBK-NSHDSACASA-N
FDA UNII
PKI06M3IW0

Rivastigmine
A carbamate-derived reversible CHOLINESTERASE INHIBITOR that is selective for the CENTRAL NERVOUS SYSTEM and is used for the treatment of DEMENTIA in ALZHEIMER DISEASE and PARKINSON DISEASE.
Rivastigmine is a Cholinesterase Inhibitor. The mechanism of action of rivastigmine is as a Cholinesterase Inhibitor.
1 2D Structure

Rivastigmine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[3-[(1S)-1-(dimethylamino)ethyl]phenyl] N-ethyl-N-methylcarbamate
2.1.2 InChI
InChI=1S/C14H22N2O2/c1-6-16(5)14(17)18-13-9-7-8-12(10-13)11(2)15(3)4/h7-11H,6H2,1-5H3/t11-/m0/s1
2.1.3 InChI Key
XSVMFMHYUFZWBK-NSHDSACASA-N
2.1.4 Canonical SMILES
CCN(C)C(=O)OC1=CC=CC(=C1)C(C)N(C)C
2.1.5 Isomeric SMILES
CCN(C)C(=O)OC1=CC=CC(=C1)[C@H](C)N(C)C
2.2 Other Identifiers
2.2.1 UNII
PKI06M3IW0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (s)-n-ethyl-3-((1-dimethyl-amino)ethyl)-n-methylphenylcarbamate

2. 713, Ena

3. 713, Sdz Ena

4. Ena 713

5. Ena 713, Sdz

6. Ena-713

7. Ena713

8. Exelon

9. Hydrogen Tartrate, Rivastigmine

10. Rivastigmine Hydrogen Tartrate

11. Rivastigminetartrate

12. Sdz Ena 713

13. Tartrate, Rivastigmine Hydrogen

2.3.2 Depositor-Supplied Synonyms

1. 123441-03-2

2. Exelon

3. Ena 713 Free Base

4. Prometax

5. Rivastigmine Teva

6. Nimvastid

7. S-rivastigmine

8. Rivastigmine Hexal

9. (s)-rivastigmine

10. (s)-3-(1-(dimethylamino)ethyl)phenyl Ethyl(methyl)carbamate

11. Rivastigmine Sandoz

12. Sdz-ena-713

13. Sdz-212-713

14. [3-[(1s)-1-(dimethylamino)ethyl]phenyl] N-ethyl-n-methylcarbamate

15. M-((s)-1-(dimethylamino)ethyl)phenyl Ethylmethylcarbamate

16. (s)-3-(1-(dimethylamino)ethyl)phenyl Ethylmethylcarbamate

17. Chembl636

18. 3-[(1s)-1-(dimethylamino)ethyl]phenyl N-ethyl-n-methylcarbamate

19. Pki06m3iw0

20. Chebi:8874

21. Ena-713d

22. Ono-2540

23. Sdz-212713

24. 3-[(1s)-1-(dimethylamino)ethyl]phenyl Ethyl(methyl)carbamate

25. Exelon Patch

26. Ethylmethylcarbamic Acid 3-[(1s)-1-(dimethylamino)ethyl]phenyl Ester

27. Sr-05000001475

28. Unii-pki06m3iw0

29. Sdz 212-713

30. Rivastigmine Transdermal System

31. Prometax (tn)

32. Rivastigmine [usan:inn:ban:jan]

33. Rivastigmine.tartrate

34. Rivastigmine Impurity D

35. 3-((1s)-1-(dimethylamino)ethyl)phenyl Ethylmethylcarbamate

36. Rivastigmine [mi]

37. Rivastigmine [inn]

38. Rivastigmine [jan]

39. Carbamic Acid, Ethylmethyl-, 3-((1s)-1-(dimethylamino)ethyl)phenyl Ester

40. Rivastigmine [usan]

41. Schembl2764

42. Rivastigmine [vandf]

43. Rivastigmine [mart.]

44. Ethylmethylcarbamic Acid 3-[1-(dimethylamino)ethyl]phenyl Ester

45. Mls003876822

46. Bidd:gt0316

47. Rivastigmine [usp-rs]

48. Rivastigmine [who-dd]

49. Rivastigmine (jan/usp/inn)

50. Gtpl6602

51. Zinc4413

52. Rivastigmine [ema Epar]

53. Rivastigmine 1 A Pharma

54. Dtxsid7023564

55. Bdbm10620

56. Bdbm11682

57. Amy3808

58. Hms2089h18

59. Hms3715p15

60. Hms3885b18

61. Rivastigmine [orange Book]

62. Rivastigmine [ep Monograph]

63. Rivastigmine [usp Monograph]

64. Mfcd00871496

65. Akos015896334

66. Carbamic Acid, Ethylmethyl-, 3-(1-(dimethylamino)ethyl)phenyl Ester, (s)-

67. Ac-8250

68. Ccg-221197

69. Cs-0946

70. Db00989

71. Rivastigmine 3m Health Care Ltd

72. Ncgc00167531-03

73. Ncgc00167531-17

74. As-73448

75. Hy-17368

76. Smr002203623

77. R0250

78. S4687

79. (r)-rivastigmine (rivastigmine Ep Impurity D)

80. D03822

81. D82061

82. F10108

83. Ab01275472-01

84. Ab01275472_02

85. Ab01275472_03

86. 101r548

87. Q411887

88. Sr-05000001475-1

89. Sr-05000001475-2

90. W-200966

91. (s)-3-[1-(dimethylamino)ethyl]phenyl N-ethyl-n-methylcarbamate

92. [3-[(1s)-1-dimethylaminoethyl]phenyl] N-ethyl-n-methylcarbamate

93. 3-((1s)-1-(dimethylamino)ethyl)phenyl N-ethyl N-methyl Carbamate

94. Ethyl-methyl-carbamic Acid 3-(1-dimethylamino-ethyl)-phenyl Ester

95. Ethyl-methyl-carbamic Acid 3-((r)-1-dimethylamino-ethyl)-phenyl Ester

96. Ethyl-methyl-carbamic Acid 3-((s)-1-dimethylamino-ethyl)-phenyl Ester

97. Carbamic Acid, N-ethyl-n-methyl-, 3-[(1s)-1-(dimethylamino)ethyl]phenyl Ester

98. 2,3-dihydroxybutanedioic Acid; 3-[(1s)-1-(dimethylamino)ethyl]phenyl N-ethyl-n-methylcarbamate

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 250.34 g/mol
Molecular Formula C14H22N2O2
XLogP32.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Exact Mass250.168127949 g/mol
Monoisotopic Mass250.168127949 g/mol
Topological Polar Surface Area32.8 Ų
Heavy Atom Count18
Formal Charge0
Complexity269
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameRivastigmine
PubMed HealthRivastigmine
Drug ClassesCentral Nervous System Agent
Drug LabelRivastigmine tartrate is a reversible cholinesterase inhibitor and is known chemically as (S)-N-Ethyl-N-methyl-3-[1-(dimethylamino)ethyl]-phenyl carbamate hydrogen-(2R,3R)-tartrate. Rivastigmine tartrate is commonly referred to in the pharmacological...
Active IngredientRivastigmine tartrate
Dosage FormSolution
Routeoral
Strength2mg/ml
Market StatusTentative Approval
CompanyRanbaxy

2 of 2  
Drug NameRivastigmine
PubMed HealthRivastigmine
Drug ClassesCentral Nervous System Agent
Drug LabelRivastigmine tartrate is a reversible cholinesterase inhibitor and is known chemically as (S)-N-Ethyl-N-methyl-3-[1-(dimethylamino)ethyl]-phenyl carbamate hydrogen-(2R,3R)-tartrate. Rivastigmine tartrate is commonly referred to in the pharmacological...
Active IngredientRivastigmine tartrate
Dosage FormSolution
Routeoral
Strength2mg/ml
Market StatusTentative Approval
CompanyRanbaxy

4.2 Drug Indication

For the treatment of mild to moderate dementia associated with Parkinson's disease or of the Alzheimer's type.


FDA Label


Symptomatic treatment of mild to moderately severe Alzheimer's dementia.

Symptomatic treatment of mild to moderately severe dementia in patients with idiopathic Parkinson's disease.


Symptomatic treatment of mild to moderately severe Alzheimer's dementia.

Symptomatic treatment of mild to moderately severe dementia in patients with idiopathic Parkinson's disease.


Symptomatic treatment of mild to moderately severe Alzheimer's dementia.

Symptomatic treatment of mild to moderately severe dementia in patients with idiopathic Parkinson's disease.


Symptomatic treatment of mild to moderately severe Alzheimer's dementia.

Symptomatic treatment of mild to moderately severe dementia in patients with idiopathic Parkinson's disease.


Symptomatic treatment of mild to moderately severe Alzheimer's dementia.

Symptomatic treatment of mild to moderately severe dementia in patients with idiopathic Parkinson's disease.


Symptomatic treatment of mild to moderately severe Alzheimer's dementia.

Symptomatic treatment of mild to moderately severe dementia in patients with idiopathic Parkinson's disease.


Symptomatic treatment of mild to moderately severe Alzheimer's dementia.


Symptomatic treatment of mild to moderately severe Alzheimer's dementia.

Symptomatic treatment of mild to moderately severe dementia in patients with idiopathic Parkinson's disease.


Treatment of dementia


Treatment of dementia


5 Pharmacology and Biochemistry
5.1 Pharmacology

Rivastigmine is a parasympathomimetic and a reversible cholinesterase inhibitor. An early pathophysiological feature of Alzheimer's disease that is associated with memory loss and cognitive deficits is a deficiency of acetylcholine as a result of selective loss of cholinergic neurons in the cerebral cortex, nucleus basalis, and hippocampus. Tacrine is postulated to exert its therapeutic effect by enhancing cholinergic function. While the precise mechanism of rivastigmine's action is unknown, it is postulated to exert its therapeutic effect by enhancing cholinergic function. This is accomplished by increasing the concentration of acetylcholine through reversible inhibition of its hydrolysis by cholinesterase. If this proposed mechanism is correct, rivastigmine's effect may lessen as the disease progresses and fewer cholinergic neurons remain functionally intact.


5.2 MeSH Pharmacological Classification

Neuroprotective Agents

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)


Cholinesterase Inhibitors

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
RIVASTIGMINE
5.3.2 FDA UNII
PKI06M3IW0
5.3.3 Pharmacological Classes
Cholinesterase Inhibitors [MoA]; Cholinesterase Inhibitor [EPC]
5.4 ATC Code

N06DA03


N06DA03


N06DA03


N06DA03


N06DA03


N06DA03


N06DA03


N06DA03


N06DA03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N06 - Psychoanaleptics

N06D - Anti-dementia drugs

N06DA - Anticholinesterases

N06DA03 - Rivastigmine


5.5 Absorption, Distribution and Excretion

Route of Elimination

Rivastigmine is extensively metabolized primarily via cholinesterase-mediated hydrolysis to the decarbamylated metabolite NAP226-90. Renal excretion of the metabolites is the major route of elimination. Less than 1% of the administered dose is excreted in the feces.


Volume of Distribution

1.8 to 2.7 L/kg


Clearance

renal cl=2.1-2.8 L/hr


5.6 Metabolism/Metabolites

Rivastigmine is rapidly metabolized by cholinesterase-mediated hydrolysis.


5.7 Biological Half-Life

1.5 hours


5.8 Mechanism of Action

Rivastigmine is a carbamate derivative that is structurally related to physostigmine, but not to donepezil and tacrine. The precise mechanism of rivastigmine has not been fully determined, but it is suggested that rivastigmine binds reversibly with and inactivates chlolinesterase (eg. acetylcholinesterase, butyrylcholinesterase), preventing the hydrolysis of acetycholine, and thus leading to an increased concentration of acetylcholine at cholinergic synapses. The anticholinesterase activity of rivastigmine is relatively specific for brain acetylcholinesterase and butyrylcholinesterase compared with those in peripheral tissues.


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11-Jan-2021
29-Aug-2024
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