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Prestwick3_000632

Prestwick3_000632

Synopsis, Chemistry

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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

Prestwick3_000632

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 Formula	C₁₉H₂₉NO₅
Molecular Weight	351.4 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	9
Exact Mass	351.20457303 g/mol
Monoisotopic Mass	351.20457303 g/mol
Topological Polar Surface Area	84.9 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	463
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.