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    Chemistry

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    Also known as: 129101-54-8, Rivastigmine hydrogen tartrate, Ena 713, Sdz-ena 713, Rivastigmine bitartrate, Rivastigmine (tartrate)
    Molecular Formula
    C18H28N2O8
    Molecular Weight
    400.4  g/mol
    InChI Key
    GWHQHAUAXRMMOT-MBANBULQSA-N
    FDA UNII
    9IY2357JPE
    Rivastigmine Tartrate
    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.
    1 2D Structure

    Rivastigmine Tartrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R,3R)-2,3-dihydroxybutanedioic acid;[3-[(1S)-1-(dimethylamino)ethyl]phenyl] N-ethyl-N-methylcarbamate
    2.1.2 InChI
    InChI=1S/C14H22N2O2.C4H6O6/c1-6-16(5)14(17)18-13-9-7-8-12(10-13)11(2)15(3)4;5-1(3(7)8)2(6)4(9)10/h7-11H,6H2,1-5H3;1-2,5-6H,(H,7,8)(H,9,10)/t11-;1-,2-/m01/s1
    2.1.3 InChI Key
    GWHQHAUAXRMMOT-MBANBULQSA-N
    2.1.4 Canonical SMILES
    CCN(C)C(=O)OC1=CC=CC(=C1)C(C)N(C)C.C(C(C(=O)O)O)(C(=O)O)O
    2.1.5 Isomeric SMILES
    CCN(C)C(=O)OC1=CC=CC(=C1)[C@H](C)N(C)C.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    9IY2357JPE
    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

    11. Rivastigmine Hydrogen Tartrate

    12. Rivastigminetartrate

    13. Sdz Ena 713

    14. Tartrate, Rivastigmine Hydrogen

    2.3.2 Depositor-Supplied Synonyms

    1. 129101-54-8

    2. Rivastigmine Hydrogen Tartrate

    3. Ena 713

    4. Sdz-ena 713

    5. Rivastigmine Bitartrate

    6. Rivastigmine (tartrate)

    7. (s)-3-(1-(dimethylamino)ethyl)phenyl Ethyl(methyl)carbamate (2r,3r)-2,3-dihydroxysuccinate

    8. Rivastigmine Hydrogentartrate

    9. Rivastigmine Tartrate (exelon)

    10. 9iy2357jpe

    11. Chebi:64358

    12. (2r,3r)-2,3-dihydroxybutanedioic Acid;[3-[(1s)-1-(dimethylamino)ethyl]phenyl] N-ethyl-n-methylcarbamate

    13. Rivastigmine Actavis

    14. (2r,3r)-2,3-dihydroxybutanedioic Acid 3-[(1s)-1-(dimethylamino)ethyl]phenyl N-ethyl-n-methylcarbamate

    15. Carbamic Acid, N-ethyl-n-methyl-, 3-[(1s)-1-(dimethylamino)ethyl]phenyl Ester, (2r,3r)-2,3-dihydroxybutanedioate (1:1)

    16. Rivastigmine Tartrate Salt

    17. Unii-9iy2357jpe

    18. Rivastach

    19. Exelon Mr

    20. Exelon Tds

    21. Nimvastid (tn)

    22. Carbamic Acid, N-ethyl-n-methyl-, 3-((1s)-1-(dimethylamino)ethyl)phenyl Ester, (2r,3r)-2,3-dihydroxybutanedioate (1:1)

    23. Rivastigmine Tartrate;

    24. Rivastigmine L-tartrate

    25. Rivastigmine Tartrate [usp]

    26. Rivastigmine Tartrate- Bio-x

    27. Mls006011143

    28. Chembl1201092

    29. Hms3678f17

    30. Hms3884h05

    31. Rivastigmine For System Suitability

    32. Act03355

    33. Mfcd03700731

    34. Rivastigmine Tartrate [vandf]

    35. S2087

    36. Akos022179413

    37. Rivastigmine Tartrate [usp-rs]

    38. Ac-3487

    39. Ccg-213410

    40. Cs-0947

    41. T01r548

    42. As-13921

    43. Br164357

    44. Carbamic Acid, Ethylmethyl-, 3-((1s)-1-(dimethylamino)ethyl)phenyl Ester, (2r,3r)-2,3-dihydroxybutanedioate (1:1)

    45. Carbamic Acid, Ethylmethyl-, 3-(1-(dimethylamino)ethyl)phenyl Ester, (s)-, (r-(r*,r*))-2,3-dihydroxybutanedioate (1:1)

    46. Hy-11017

    47. N-ethyl-n-methylcarbamic Acid 3-[(1s)-1-(dimethylamino)ethyl]phenyl Ester (2r,3r)-2,3-dihydroxybutanedioate

    48. Smr004702920

    49. Rivastigmine (as Hydrogen Tartrate)

    50. Rivastigmine Hydrogen Tartrate [mi]

    51. Rivastigmine Tartrate [orange Book]

    52. Am20080949

    53. R0093

    54. Rivastigmine Tartrate [usp Monograph]

    55. Sw199663-2

    56. Rivastigmine Hydrogen Tartrate [mart.]

    57. D02558

    58. Rivastigmine Hydrogen Tartrate [who-dd]

    59. Rivastigmine Hydrogen Tartrate [ema Epar]

    60. Q-101313

    61. Rivastigmine Hydrogen Tartrate [ep Monograph]

    62. Q27133236

    63. 3-[(s)-1-(dimethylamino)ethyl]phenyl N-ethyl-n-methylcarbamate L-tartrate

    64. N-ethyl-n-methylcarbamic Acid 3-[(s)-1-(dimethylamino)ethyl]phenyl Ester L-tartrate

    65. (1s)-1-(3-{[ethyl(methyl)carbamoyl]oxy}phenyl)-n,n-dimethylethanaminium (2r,3r)-3-carboxy-2,3-dihydroxypropanoate

    66. 3-[(1s)-1-(dimethylamino)ethyl]phenyl Ethyl(methyl)carbamate (2r,3r)-2,3-dihydroxybutanedioate

    2.4 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 400.4 g/mol
    Molecular Formula C18H28N2O8
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count8
    Exact Mass400.18456586 g/mol
    Monoisotopic Mass400.18456586 g/mol
    Topological Polar Surface Area148 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity402
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameRivastigmine tartrate
    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 FormCapsule
    Routeoral; Oral
    Strengtheq 4.5mg base; eq 6mg base; eq 1.5mg base; eq 3mg base
    Market StatusTentative Approval; Prescription
    CompanyApotex; Alembic Pharms; Sun Pharm Inds; Watson Labs; Macleods Pharms; Dr Reddys Labs; Orchid Hlthcare

    2 of 2  
    Drug NameRivastigmine tartrate
    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 FormCapsule
    Routeoral; Oral
    Strengtheq 4.5mg base; eq 6mg base; eq 1.5mg base; eq 3mg base
    Market StatusTentative Approval; Prescription
    CompanyApotex; Alembic Pharms; Sun Pharm Inds; Watson Labs; Macleods Pharms; Dr Reddys Labs; Orchid Hlthcare

    4.2 Drug Indication

    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.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    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.)

    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.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Cholinesterase Inhibitors [MoA]; Cholinesterase Inhibitor [EPC]
    5.3 ATC Code

    N06DA03

    API Reference Price

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    19-Jan-2021
    10-Jul-2024
    KGS
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    Average Price (USD/KGS)

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    DOSAGE - CAPSULE;ORAL - EQ 1.5MG BASE **Feder...DOSAGE - CAPSULE;ORAL - EQ 1.5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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    DOSAGE - CAPSULE;ORAL - EQ 3MG BASE **Federal...DOSAGE - CAPSULE;ORAL - EQ 3MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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    DOSAGE - CAPSULE;ORAL - EQ 4.5MG BASE **Feder...DOSAGE - CAPSULE;ORAL - EQ 4.5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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    DOSAGE - CAPSULE;ORAL - EQ 6MG BASE **Federal...DOSAGE - CAPSULE;ORAL - EQ 6MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20823

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