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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
    KGS
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