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    Chemistry

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    Also known as: 173334-58-2, Tekturna, Aliskiren fumarate, Aliskiren (hemifumarate), Enviage, Riprazo
    Molecular Formula
    C64H110N6O16
    Molecular Weight
    1219.6  g/mol
    InChI Key
    KLRSDBSKUSSCGU-KRQUFFFQSA-N
    FDA UNII
    C8A0P8G029
    Aliskiren
    Aliskiren Hemifumarate is an orally active nonpeptide renin inhibitor with antihypertensive activity. Aliskiren selectively binds to the S3 sub-pocket of renin, an enzyme in the renin-angiotensin-aldosterone system (RAAS) that is responsible for converting angiotensinogen to angiotensin I (AT I). By inhibiting the activity of renin, the conversion to AT I is prevented, which in turn prevents the conversion of AT I to AT II. This prevents arterial vasoconstriction by AT II and inhibits the production of aldosterone by AT II. As aldosterone causes re-uptake of sodium and water and eventually an increase in extracellular volume, aliskiren is able to prevent the effects that contribute to an increase in blood pressure.
    1 2D Structure

    Aliskiren

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-2-propan-2-ylnonanamide;(E)-but-2-enedioic acid
    2.1.2 InChI
    InChI=1S/2C30H53N3O6.C4H4O4/c2*1-19(2)22(14-21-10-11-26(38-8)27(15-21)39-13-9-12-37-7)16-24(31)25(34)17-23(20(3)4)28(35)33-18-30(5,6)29(32)36;5-3(6)1-2-4(7)8/h2*10-11,15,19-20,22-25,34H,9,12-14,16-18,31H2,1-8H3,(H2,32,36)(H,33,35);1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*22-,23-,24-,25-;/m00./s1
    2.1.3 InChI Key
    KLRSDBSKUSSCGU-KRQUFFFQSA-N
    2.1.4 Canonical SMILES
    CC(C)C(CC1=CC(=C(C=C1)OC)OCCCOC)CC(C(CC(C(C)C)C(=O)NCC(C)(C)C(=O)N)O)N.CC(C)C(CC1=CC(=C(C=C1)OC)OCCCOC)CC(C(CC(C(C)C)C(=O)NCC(C)(C)C(=O)N)O)N.C(=CC(=O)O)C(=O)O
    2.1.5 Isomeric SMILES
    CC(C)[C@@H](CC1=CC(=C(C=C1)OC)OCCCOC)C[C@@H]([C@H](C[C@@H](C(C)C)C(=O)NCC(C)(C)C(=O)N)O)N.CC(C)[C@@H](CC1=CC(=C(C=C1)OC)OCCCOC)C[C@@H]([C@H](C[C@@H](C(C)C)C(=O)NCC(C)(C)C(=O)N)O)N.C(=C/C(=O)O)\C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    C8A0P8G029
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2(s),4(s),5(s),7(s)-n-(2-carbamoyl-2-methylpropyl)-5-amino-4-hydroxy-2,7-diisopropyl-8-(4-methoxy-3-(3-methoxypropoxy)phenyl)octanamid Hemifumarate

    2. Aliskiren

    3. Cgp 060536b

    4. Cgp-060536b

    5. Cgp060536b

    6. Rasilez

    7. Spp100

    8. Tekturna

    2.3.2 Depositor-Supplied Synonyms

    1. 173334-58-2

    2. Tekturna

    3. Aliskiren Fumarate

    4. Aliskiren (hemifumarate)

    5. Enviage

    6. Riprazo

    7. Sprimeo

    8. Spp-100b

    9. Chebi:53777

    10. C8a0p8g029

    11. Nsc-759185

    12. Cgp 60536

    13. Aliskirenfumarate

    14. (2s,4s,5s,7s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-2-propan-2-ylnonanamide;(e)-but-2-enedioic Acid

    15. Cgp60536b

    16. Bis(2s,4s,5s,7s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methyl-2-(1-methylethyl)nonanamide) (2e)-but-2-enedioate

    17. Aliskiren Fumarate [usan]

    18. Unii-c8a0p8g029

    19. Aliskiren Fumarate [usan:jan]

    20. Tekturna (tn)

    21. Cgp-60536

    22. Aliskiren Hemifumarate- Bio-x

    23. Schembl187762

    24. Aliskiren (as Fumarate)

    25. Aliskiren Fumarate (jan/usan)

    26. Aliskiren Fumarate [jan]

    27. Chembl3545059

    28. Cgp-60536b

    29. Aliskiren Fumarate [mart.]

    30. Aliskiren Hemifumarate [mi]

    31. Aliskiren Fumarate [who-dd]

    32. Mfcd10566724

    33. S2199

    34. Aliskiren Hemifumarate [vandf]

    35. Akos015896419

    36. Ccg-270658

    37. Cs-0729

    38. Ks-1395

    39. Nsc 759185

    40. S12129

    41. (2s,4s,5s,7s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonanamide Hemifumarate

    42. Ba164146

    43. Hy-12177

    44. Aliskiren Hemifumarate [orange Book]

    45. Sw222231-1

    46. D06412

    47. Rasitrio Component Aliskiren Hemifumarate

    48. Tekamlo Component Aliskiren Hemifumarate

    49. Valturna Component Aliskiren Hemifumarate

    50. Amturnide Component Aliskiren Hemifumarate

    51. Rasilamlo Component Aliskiren Hemifumarate

    52. Aliskiren Hemifumarate Component Of Rasitrio

    53. Aliskiren Hemifumarate Component Of Tekamlo

    54. Aliskiren Hemifumarate Component Of Valturna

    55. Raprazo-hct Component Aliskiren Hemifumarate

    56. Rasilez-hct Component Aliskiren Hemifumarate

    57. Sprimeo-hct Component Aliskiren Hemifumarate

    58. Aliskiren Hemifumarate Component Of Amturnide

    59. Aliskiren Hemifumarate Component Of Rasilamlo

    60. Tekturna Hct Component Aliskiren Hemifumarate

    61. Aliskiren Hemifumarate Component Of Raprazo-hct

    62. Aliskiren Hemifumarate Component Of Rasilez-hct

    63. Aliskiren Hemifumarate Component Of Sprimeo-hct

    64. Q27124205

    65. Aliskiren Hemifumarate Component Of Tekturna Hct

    66. (?s,?s,?s,?s)-?-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-?-hydroxy-4-methoxy-3-(3-methoxypropoxy)-?,?-bis(1-methylethyl)benzeneoctanamide Hemifumarate

    67. 5-amino-n-(3-amino-2,2-dime-3-oxoprop)-4-oh-2-isoprop-7-[4-meo-3-(3-meo-propoxy)benzyl]-8-methylnonanamide Hemifumarate

    68. Benzeneoctanamide, Delta-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-gamma-hydroxy-4-methoxy-3-(3-methoxypropoxy)-alpha,zeta-bis(1-methylethyl)-, (alphas,gammas,deltas,zetas)-, (2e)-2-butenedioate (2:1) (salt)

    69. Bis((2s,4s,5s,7s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonanamide) Fumarate

    70. Bis{(2s,4s,5s,7s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methyl-2-(propan-2-yl)nonanamide} (2e)-but-2-enedioate

    2.4 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 1219.6 g/mol
    Molecular Formula C64H110N6O16
    Hydrogen Bond Donor Count10
    Hydrogen Bond Acceptor Count18
    Rotatable Bond Count40
    Exact Mass1218.79783144 g/mol
    Monoisotopic Mass1218.79783144 g/mol
    Topological Polar Surface Area367 Ų
    Heavy Atom Count86
    Formal Charge0
    Complexity836
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameTekturna
    PubMed HealthAliskiren (By mouth)
    Drug ClassesAntihypertensive
    Drug LabelTekturna contains aliskiren hemifumarate, a renin inhibitor, that is provided as tablets for oral administration. Aliskiren hemifumarate is chemically described as (2S,4S,5S,7S)-N-(2-carbamoyl-2-methylpropyl)-5-amino-4-hydroxy-2,7-diisopropyl-8-[4-me...
    Active IngredientAliskiren hemifumarate
    Dosage FormTablet
    RouteOral
    Strengtheq 150mg base; eq 300mg base
    Market StatusPrescription
    CompanyNovartis

    2 of 2  
    Drug NameTekturna
    PubMed HealthAliskiren (By mouth)
    Drug ClassesAntihypertensive
    Drug LabelTekturna contains aliskiren hemifumarate, a renin inhibitor, that is provided as tablets for oral administration. Aliskiren hemifumarate is chemically described as (2S,4S,5S,7S)-N-(2-carbamoyl-2-methylpropyl)-5-amino-4-hydroxy-2,7-diisopropyl-8-[4-me...
    Active IngredientAliskiren hemifumarate
    Dosage FormTablet
    RouteOral
    Strengtheq 150mg base; eq 300mg base
    Market StatusPrescription
    CompanyNovartis

    4.2 Drug Indication

    Treatment of essential hypertension.

    Treatment of essential hypertension.

    Treatment of essential hypertension

    Treatment of essential hypertension

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Pharmacological Classes
    Renin Inhibitors [MoA]; Renin Inhibitor [EPC]
    5.2 ATC Code

    C09XA02

    C09XA02

    C09XA02

    C09XA02

    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - TABLET;ORAL - EQ 150MG BASE

    USFDA APPLICATION NUMBER - 21985

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    DOSAGE - TABLET;ORAL - EQ 300MG BASE

    USFDA APPLICATION NUMBER - 21985

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    DOSAGE - TABLET;ORAL - EQ 150MG BASE;12.5MG *...DOSAGE - TABLET;ORAL - EQ 150MG BASE;12.5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 22107

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    DOSAGE - TABLET;ORAL - EQ 150MG BASE;25MG **F...DOSAGE - TABLET;ORAL - EQ 150MG BASE;25MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 22107

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    DOSAGE - TABLET;ORAL - EQ 300MG BASE;12.5MG *...DOSAGE - TABLET;ORAL - EQ 300MG BASE;12.5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 22107

    read-more

    DOSAGE - TABLET;ORAL - EQ 300MG BASE;25MG **F...DOSAGE - TABLET;ORAL - EQ 300MG BASE;25MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 22107

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