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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
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

Dipivefrin

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.


REF. STANDARDS & IMPURITIES

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ABOUT THIS PAGE

Dipivefrin Manufacturers

A Dipivefrin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Dipivefrin, including repackagers and relabelers. The FDA regulates Dipivefrin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Dipivefrin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Dipivefrin Suppliers

A Dipivefrin supplier is an individual or a company that provides Dipivefrin active pharmaceutical ingredient (API) or Dipivefrin finished formulations upon request. The Dipivefrin suppliers may include Dipivefrin API manufacturers, exporters, distributors and traders.

click here to find a list of Dipivefrin suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Dipivefrin USDMF

A Dipivefrin DMF (Drug Master File) is a document detailing the whole manufacturing process of Dipivefrin active pharmaceutical ingredient (API) in detail. Different forms of Dipivefrin DMFs exist exist since differing nations have different regulations, such as Dipivefrin USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Dipivefrin DMF submitted to regulatory agencies in the US is known as a USDMF. Dipivefrin USDMF includes data on Dipivefrin's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Dipivefrin USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Dipivefrin suppliers with USDMF on PharmaCompass.

Dipivefrin GMP

Dipivefrin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Dipivefrin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Dipivefrin GMP manufacturer or Dipivefrin GMP API supplier for your needs.

Dipivefrin CoA

A Dipivefrin CoA (Certificate of Analysis) is a formal document that attests to Dipivefrin's compliance with Dipivefrin specifications and serves as a tool for batch-level quality control.

Dipivefrin CoA mostly includes findings from lab analyses of a specific batch. For each Dipivefrin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Dipivefrin may be tested according to a variety of international standards, such as European Pharmacopoeia (Dipivefrin EP), Dipivefrin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Dipivefrin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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