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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


NDC API

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01

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RIVASTIGMINE TARTRATE

NDC Package Code : 65862-612

Start Marketing Date : 2023-12-18

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (50kg/50kg)

Marketing Category : BULK INGREDIENT

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02

Cipla Ltd.

India
Antibody Engineering
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Cipla Ltd.

India
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Antibody Engineering
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RIVASTIGMINE TARTRATE

NDC Package Code : 53104-7571

Start Marketing Date : 2016-01-01

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (25kg/25kg)

Marketing Category : BULK INGREDIENT

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03

Antibody Engineering
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RIVASTIGMINE TARTRATE

NDC Package Code : 49706-1826

Start Marketing Date : 2010-01-08

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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04

Antibody Engineering
Not Confirmed
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Antibody Engineering
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RIVASTIGMINE TARTRATE

NDC Package Code : 65372-1152

Start Marketing Date : 2011-01-10

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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05

Antibody Engineering
Not Confirmed
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Antibody Engineering
Not Confirmed

RIVASTIGMINE TARTRATE

NDC Package Code : 50379-0012

Start Marketing Date : 2014-03-24

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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API Reference Price

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09-Mar-2021
21-Oct-2024
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Quantity (KGS) & Unit rate (USD/KGS) over time

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Drugs in Development

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Details:

Through the acquisition, Almirall get exclusive rights to commercialize the Prometax (rivastigmine hydrogen tartrate), a multi-day transdermal patch for the treatment of Alzheimer’s disease.


Lead Product(s): Rivastigmine Tartrate

Therapeutic Area: Neurology Brand Name: Prometax

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Almirall

Deal Size: $64.2 million Upfront Cash: $48.1 million

Deal Type: Acquisition September 04, 2023

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Antibody Engineering
Not Confirmed
Antibody Engineering
Not Confirmed

Details : Through the acquisition, Almirall get exclusive rights to commercialize the Prometax (rivastigmine hydrogen tartrate), a multi-day transdermal patch for the treatment of Alzheimer’s disease.

Brand Name : Prometax

Molecule Type : Small molecule

Upfront Cash : $48.1 million

September 04, 2023

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Details:

Exelon (rivastigmine tartrate) is an oral acetylcholinesterase inhibitor, which is approved for the treatment of mild to moderately severe dementia in people with Alzheimer's disease and Parkinson's disease..


Lead Product(s): Rivastigmine Tartrate

Therapeutic Area: Neurology Brand Name: Exelon

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable August 15, 2022

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02

Antibody Engineering
Not Confirmed
Antibody Engineering
Not Confirmed

Details : Exelon (rivastigmine tartrate) is an oral acetylcholinesterase inhibitor, which is approved for the treatment of mild to moderately severe dementia in people with Alzheimer's disease and Parkinson's disease..

Brand Name : Exelon

Molecule Type : Small molecule

Upfront Cash : Not Applicable

August 15, 2022

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Details:

Exelon (rivastigmine tartrate) is an oral acetylcholinesterase inhibitor, which is approved for the treatment of mild to moderately severe dementia in people with Alzheimer's disease and Parkinson's disease..


Lead Product(s): Rivastigmine Tartrate

Therapeutic Area: Neurology Brand Name: Exelon

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable June 01, 2022

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03

Antibody Engineering
Not Confirmed
Antibody Engineering
Not Confirmed

Details : Exelon (rivastigmine tartrate) is an oral acetylcholinesterase inhibitor, which is approved for the treatment of mild to moderately severe dementia in people with Alzheimer's disease and Parkinson's disease..

Brand Name : Exelon

Molecule Type : Small molecule

Upfront Cash : Not Applicable

June 01, 2022

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Details:

Knight Therapeutics has acquired exclusive rights to manufacture, market and sell Exelon® (rivastigmine Patch, Capsules and Solution) in Canada and Latin America, as well as an exclusive license to use the intellectual property and the Exelon trademark, from Novartis.


Lead Product(s): Rivastigmine Tartrate

Therapeutic Area: Neurology Brand Name: Exelon

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Knight Therapeutics

Deal Size: $180.0 million Upfront Cash: $168.0 million

Deal Type: Acquisition May 26, 2021

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04

Antibody Engineering
Not Confirmed
Antibody Engineering
Not Confirmed

Details : Knight Therapeutics has acquired exclusive rights to manufacture, market and sell Exelon® (rivastigmine Patch, Capsules and Solution) in Canada and Latin America, as well as an exclusive license to use the intellectual property and the Exelon trademark,...

Brand Name : Exelon

Molecule Type : Small molecule

Upfront Cash : $168.0 million

May 26, 2021

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Details:

Exelon (rivastigmine) is a prescription product that was first approved in 1997 and is currently registered and sold in approximately 90 countries. Exelon is indicated for the symptomatic treatment of mild to moderately severe dementia in people with Alzheimer's disease.


Lead Product(s): Rivastigmine Tartrate

Therapeutic Area: Neurology Brand Name: Exelon

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Knight Therapeutics

Deal Size: $180.0 million Upfront Cash: $168.0 million

Deal Type: Acquisition April 23, 2021

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05

Antibody Engineering
Not Confirmed
Antibody Engineering
Not Confirmed

Details : Exelon (rivastigmine) is a prescription product that was first approved in 1997 and is currently registered and sold in approximately 90 countries. Exelon is indicated for the symptomatic treatment of mild to moderately severe dementia in people with Alz...

Brand Name : Exelon

Molecule Type : Small molecule

Upfront Cash : $168.0 million

April 23, 2021

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INTERMEDIATES SUPPLIERS

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CAS Number : 42252-34-6

End Use API : Rivastigmine Tartrate

About The Company : Founded in 2003, Senary Chem is one of the Key High-Tech Enterprises of National Torch Plan. Senary located in National Cangzhou Lingang Economic and Technologi...

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Antibody Engineering
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Antibody Engineering
Not Confirmed
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CAS Number : 139306-10-8

End Use API : Rivastigmine Tartrate

About The Company : Founded in 2003, Senary Chem is one of the Key High-Tech Enterprises of National Torch Plan. Senary located in National Cangzhou Lingang Economic and Technologi...

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03

Antibody Engineering
Not Confirmed
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Antibody Engineering
Not Confirmed
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CAS Number : 105601-04-5

End Use API : Rivastigmine Tartrate

About The Company : Founded in 2003, Senary Chem is one of the Key High-Tech Enterprises of National Torch Plan. Senary located in National Cangzhou Lingang Economic and Technologi...

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04

Antibody Engineering
Not Confirmed
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Antibody Engineering
Not Confirmed
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CAS Number : 105601-04-5

End Use API : Rivastigmine Tartrate

About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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05

Antibody Engineering
Not Confirmed
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Antibody Engineering
Not Confirmed
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CAS Number : 139306-10-8

End Use API : Rivastigmine Tartrate

About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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06

Antibody Engineering
Not Confirmed
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Antibody Engineering
Not Confirmed
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CAS Number : 42252-34-6

End Use API : Rivastigmine Tartrate

About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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07

Antibody Engineering
Not Confirmed
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Antibody Engineering
Not Confirmed
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CAS Number : 105601-04-5

End Use API : Rivastigmine Tartrate

About The Company : Prajna is an innovation driven pharmaceutical company. We dedicated to Research, Process development and Manufacturing APIs and Advanced Intermediates for Activ...

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08

Antibody Engineering
Not Confirmed
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Antibody Engineering
Not Confirmed
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CAS Number : 63720-38-7

End Use API : Rivastigmine Tartrate

About The Company : Prajna is an innovation driven pharmaceutical company. We dedicated to Research, Process development and Manufacturing APIs and Advanced Intermediates for Activ...

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09

Antibody Engineering
Not Confirmed
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Antibody Engineering
Not Confirmed
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CAS Number : 123441-03-2

End Use API : Rivastigmine Tartrate

About The Company : Prajna is an innovation driven pharmaceutical company. We dedicated to Research, Process development and Manufacturing APIs and Advanced Intermediates for Activ...

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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**

USFDA APPLICATION NUMBER - 20823

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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**

USFDA APPLICATION NUMBER - 20823

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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**

USFDA APPLICATION NUMBER - 20823

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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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