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Rivastigmine Tartrate

Synopsis, Chemistry

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CAPSULE;ORAL - EQ 1.5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, CAPSULE;ORAL - EQ 3MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, CAPSULE;ORAL - EQ 4.5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, CAPSULE;ORAL - EQ 6MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

CAPSULE;ORAL - EQ 1.5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**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

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 Formula	C₁₈H₂₈N₂O₈
Molecular Weight	400.4 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	8
Exact Mass	400.18456586 g/mol
Monoisotopic Mass	400.18456586 g/mol
Topological Polar Surface Area	148 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	402
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Rivastigmine tartrate
Drug Label	Rivastigmine 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 Ingredient	Rivastigmine tartrate
Dosage Form	Capsule
Route	oral; Oral
Strength	eq 4.5mg base; eq 6mg base; eq 1.5mg base; eq 3mg base
Market Status	Tentative Approval; Prescription
Company	Apotex; Alembic Pharms; Sun Pharm Inds; Watson Labs; Macleods Pharms; Dr Reddys Labs; Orchid Hlthcare

2 of 2
Drug Name	Rivastigmine tartrate
Drug Label	Rivastigmine 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 Ingredient	Rivastigmine tartrate
Dosage Form	Capsule
Route	oral; Oral
Strength	eq 4.5mg base; eq 6mg base; eq 1.5mg base; eq 3mg base
Market Status	Tentative Approval; Prescription
Company	Apotex; 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