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Chemistry

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Also known as: 64019-93-8, Dipivefrine hydrochloride, Dipivefrin hcl, Dipivefrin (hydrochloride), Akpro, 5qth9uhv0k

Molecular Formula

C₁₉H₃₀ClNO₅

Molecular Weight

387.9 g/mol

InChI Key

VKFAUCPBMAGVRG-UHFFFAOYSA-N

FDA UNII

5QTH9UHV0K

Dipivefrin Hydrochloride is an ester with sympathomimetic activities. Dipivefrin hydrochloride is a prodrug of epinephrine that, due to its greater lipophilicity, allows for better penetration into the anterior chamber. Once inside the eye, dipivefrin hydrochloride is converted by hydrolysis to epinephrine. Epinephrine enhances the outflow of aqueous humor and decreases the production of aqueous humor by vasoconstriction. This leads to a reduction in intraocular pressure.

1 2D Structure

Dipivefrin Hydrochloride

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;hydrochloride

2.1.2 InChI

InChI=1S/C19H29NO5.ClH/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;1H

2.1.3 InChI Key

VKFAUCPBMAGVRG-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.Cl

2.2 Other Identifiers

2.2.1 UNII

5QTH9UHV0K

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

15. Dipivefrin Acetate, (+-)-isomer

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

17. Dipivefrin Hcl

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. 64019-93-8

2. Dipivefrine Hydrochloride

3. Dipivefrin Hcl

4. Dipivefrin (hydrochloride)

5. Akpro

6. 5qth9uhv0k

7. Dipivefrine (hydrochloride)

8. Chebi:4647

9. (1)-4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene Dipivalate Hydrochloride

10. 64019-93-8 (hcl)

11. Dipivalyl Epinephrine Hydrochloride

12. Einecs 264-609-5

13. Unii-5qth9uhv0k

14. Dipivefrine Hcl

15. Dipivefrin Hydrochloride [jan]

16. Dipivefrin Hydrochloride [usp:jan]

17. Propine (tn)

18. Ncgc00016906-01

19. Cas-64019-93-8

20. (+-)-3,4-dihydroxy-alpha-((methylamino)methyl)benzyl Alcohol 3,4-dipivalate Hydrochloride

21. Dsstox_cid_25494

22. Dsstox_rid_80914

23. Dsstox_gsid_45494

24. Schembl41350

25. Mls002153922

26. Chembl1200833

27. Dtxsid2045494

28. Dipivefrine For System Suitability

29. Hms1569p06

30. Bcp13649

31. Hy-b1323

32. Dipivefrin Hydrochloride (jan/usp)

33. Tox21_110675

34. Dipivefrin Hydrochloride [mi]

35. Akos037515482

36. Ccg-220632

37. Dipivefrine Hydrochloride [jan]

38. Dipivalylepinephrine Hydrochloride

39. Dipivefrin Hydrochloride [vandf]

40. Dipivefrine Hydrochloride [mart.]

41. [2-(2,2-dimethylpropanoyloxy)-4-[1-hydroxy-2-(methylamino)ethyl]phenyl] 2,2-dimethylpropanoate;hydrochloride

42. Dipivefrine Hydrochloride [who-dd]

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

44. Smr001233266

45. Cs-0013083

46. Dipivefrin Hydrochloride [orange Book]

47. D01017

48. Dipivefrin Hydrochloride [usp Monograph]

49. Dipivefrine Hydrochloride [ep Monograph]

50. 019d938

51. Sr-01000838856

52. Sr-01000838856-2

53. Q27106427

54. 1-(3',4'-dipivaloyloxyphenyl)-2-methylamino-1-ethanol Hydrochloride

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

56. 2-{3,4-bis[(2,2-dimethylpropanoyl)oxy]phenyl}-2-hydroxy-n-methylethanaminium Chloride

57. (+/-)-3,4-dihydroxy-.alpha.-((methylamino)methyl)benzyl Alcohol 3,4-dipivalate Hydrochloride

58. 2-[(2,2-dimethylpropanoyl)oxy]-4-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate Hydrochloride

59. 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diyl Bis(2,2-dimethylpropanoate) Hydrochloride

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

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₃₀ClNO₅
Molecular Weight	387.9 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	9
Exact Mass	387.1812508 g/mol
Monoisotopic Mass	387.1812508 g/mol
Topological Polar Surface Area	84.9 Å²
Heavy Atom Count	26
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	2