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    Dipivefrin

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    REF. STANDARDS & IMPURITIES

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    2D Structure
    Also known as: Dipivefrine, 52365-63-6, Dipivefrinum, Dipivalyl epinephrine, Dipivefrin [usan], Dipivefrina
    Molecular Formula
    C19H29NO5
    Molecular Weight
    351.4  g/mol
    InChI Key
    OCUJLLGVOUDECM-UHFFFAOYSA-N
    FDA UNII
    8Q1PVL543G
    Dipivefrin is an ester prodrug of epinephrine, with sympathomimetic activity. Due to its lipophilicity, dipivefrin penetrates more easily to the anterior chamber of the eye and is hydrolyzed to epinephrine, when applied locally. Epinephrine, an adrenergic agonist, enhances the outflow of aqueous humor and decreases the production of aqueous humor by vasoconstriction. The overall result is a reduction in intraocular pressure.
    Dipivefrin is an Adrenergic Receptor Agonist. The mechanism of action of dipivefrin is as an Adrenergic Agonist.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [2-(2,2-dimethylpropanoyloxy)-4-[1-hydroxy-2-(methylamino)ethyl]phenyl] 2,2-dimethylpropanoate
    2.1.2 InChI
    InChI=1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3
    2.1.3 InChI Key
    OCUJLLGVOUDECM-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)(C)C(=O)OC1=C(C=C(C=C1)C(CNC)O)OC(=O)C(C)(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    8Q1PVL543G
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (+)-dipivefrin

    2. (-)-dipivefrin

    3. (r)-dipivefrine

    4. (rs)-4-(1-hydroxy-2-(methylamino)ethyl)-o-phenylene Dipivalate Hydrochloride

    5. (s)-dipivefrin

    6. (s)-dipivefrine

    7. Adrenaline Dipivalate

    8. Akpro

    9. Apo-dipivefrin

    10. D Epifrin

    11. Diopine

    12. Dipivaloylepinephrine

    13. Dipivalyl Epinephrine

    14. Dipivefrin Acetate, (+-)-isomer

    15. Dipivefrin Citrate (1:1), (+-)-isomer

    16. Dipivefrin Hcl

    17. Dipivefrin Hydrochloride

    18. Dipivefrin Hydrochloride, (+-)-isomer

    19. Dipivefrin Hydrochloride, (r)-

    20. Dipivefrin Hydrochloride, (s)-

    21. Dipivefrin Monophosphate, (+-)-isomer

    22. Dipivefrin Monosulfate, (+-)-isomer

    23. Dipivefrin Nitrate, (+-)-isomer

    24. Dipivefrin Perchlorate

    25. Dipivefrin Propanoate, (+-)-isomer

    26. Dipivefrin Tartrate (1:1), (+-)-(r-(r*,r*))-isomer

    27. Dipivefrin Tartrate (1:1), (r)-(r-(r*,r*))-isomer

    28. Dipivefrin, (r)-isomer

    29. Dipivefrine

    30. Dipivefrine Hydrochloride

    31. Dipivefrine Hydrochloride, (r)-

    32. Dipivefrine Hydrochloride, (s)-

    33. Dipivefrine, (r)-

    34. Dipoquin

    35. Glaucothil

    36. Glaudrops

    37. Pms-dipivefrin

    38. Propanoic Acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene Ester, (+-)-

    39. Propanoic Acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene Ester, (r)-

    40. Propanoic Acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene Ester, (s)-

    41. Propine

    42. Ratio-dipivefrin

    2.3.2 Depositor-Supplied Synonyms

    1. Dipivefrine

    2. 52365-63-6

    3. Dipivefrinum

    4. Dipivalyl Epinephrine

    5. Dipivefrin [usan]

    6. Dipivefrina

    7. Dipivefrine (inn)

    8. Dipivefrine [inn]

    9. Dipivefrin (usan)

    10. 8q1pvl543g

    11. Chebi:4646

    12. 1-(3',4'-dipivaloyloxyphenyl)-2-methylamino-1-ethanol

    13. 4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene Divavalate

    14. Dipivefrinum [inn-latin]

    15. Dipivefrina [inn-spanish]

    16. 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene Bis(2,2-dimethylpropanoate)

    17. K 30081

    18. Unii-8q1pvl543g

    19. 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylen Dipivalat

    20. 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene Bis(2,2-dimethylpropanoate)

    21. (+-)-3,4-dihydroxy-alpha-((methylamino)methyl)benzyl Alcohol 3,4-dipivalate

    22. [2-(2,2-dimethylpropanoyloxy)-4-[1-hydroxy-2-(methylamino)ethyl]phenyl] 2,2-dimethylpropanoate

    23. Dipivefrin [mi]

    24. (rs)-4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylen Dipivalat

    25. Prestwick0_000632

    26. Prestwick1_000632

    27. Prestwick2_000632

    28. Prestwick3_000632

    29. Dipivefrin [vandf]

    30. Dipivefrine [mart.]

    31. Propanoic Acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene Ester, (+-)-

    32. Schembl24713

    33. Bspbio_000624

    34. Dipivefrine [who-dd]

    35. Spbio_002843

    36. Bpbio1_000688

    37. Gtpl7166

    38. Chembl1201262

    39. Dtxsid1048544

    40. (+-)-4-(1-hydroxy-2-methylaminoethyl)-o-phenylendipivalat

    41. (+-)-4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene Divavalate

    42. Db00449

    43. (+-)-2,2-dimethylpropansaeure-4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylenester

    44. 2,2-dimethylpropanoic Acid 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene Ester

    45. 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diyl Bis(2,2-dimethylpropanoate)

    46. Ncgc00179499-01

    47. Ncgc00179499-05

    48. Hy-121398

    49. Ab00514686

    50. Cs-0081941

    51. Ft-0745765

    52. C06963

    53. D02349

    54. 365d636

    55. L000915

    56. Q905952

    57. Brd-a47494775-003-03-0

    58. (+/-)-4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene Divavalate

    59. Bispivalic Acid 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene Ester

    60. 2-[(2,2-dimethylpropanoyl)oxy]-4-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate

    61. 2-[(2,2-dimethylpropanoyl)oxy]-5-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate

    62. Propanoic Acid, 2,2-dimethyl-, 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene Ester, (+/-)-

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 351.4 g/mol
    Molecular Formula C19H29NO5
    XLogP32.9
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count9
    Exact Mass351.20457303 g/mol
    Monoisotopic Mass351.20457303 g/mol
    Topological Polar Surface Area84.9 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity463
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Dipivefrin is a prodrug which is used as initial therapy for the control of intraocular pressure in chronic open-angle glaucoma.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Dipivefrin is a member of a class of drugs known as prodrugs. Prodrugs are usually not active in themselves and require biotransformation to the parent compound before therapeutic activity is seen. These modifications are undertaken to enhance absorption, decrease side effects and enhance stability and comfort, thus making the parent compound a more useful drug. Enhanced absorption makes the prodrug a more efficient delivery system for the parent drug because less drug will be needed to produce the desired therapeutic response. Dipivefrin is a prodrug of epinephrine formed by the diesterification of epinephrine and pivalic acid. The addition of pivaloyl groups to the epinephrine molecule enhances its lipophilic character and, as a consequence, its penetration into the anterior chamber.

    5.2 MeSH Pharmacological Classification

    Adrenergic Agonists

    Drugs that bind to and activate adrenergic receptors. (See all compounds classified as Adrenergic Agonists.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    DIPIVEFRIN
    5.3.2 FDA UNII
    8Q1PVL543G
    5.3.3 Pharmacological Classes
    Established Pharmacologic Class [EPC] - Adrenergic Receptor Agonist
    5.4 ATC Code

    S - Sensory organs

    S01 - Ophthalmologicals

    S01E - Antiglaucoma preparations and miotics

    S01EA - Sympathomimetics in glaucoma therapy

    S01EA02 - Dipivefrine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Well absorbed following occular administration.

    5.6 Metabolism/Metabolites

    Dipivefrin is converted to epinephrine inside the human eye by enzyme hydrolysis.

    5.7 Mechanism of Action

    Dipivefrin is a prodrug with little or no pharmacologically activity until it is hydrolyzed into epinephrine inside the human eye. The liberated epinephrine, an adrenergic agonist, appears to exert its action by stimulating -and/or 2-adrenergic receptors, leading to a decrease in aqueous production and an enhancement of outflow facility. The dipivefrin prodrug delivery system is a more efficient way of delivering the therapeutic effects of epinephrine, with fewer side effects than are associated with conventional epinephrine therapy.