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Prestwick3_000959

Prestwick3_000959

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Also known as: Proxymetacaine, 499-67-2, 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate, Ophthaine, Proximetacainum, Paracaine

Molecular Formula

C₁₆H₂₆N₂O₃

Molecular Weight

294.39 g/mol

InChI Key

KCLANYCVBBTKTO-UHFFFAOYSA-N

FDA UNII

B4OB0JHI1X

Proparacaine is a benzoic acid derivative anesthetic agent, with local anesthetic activity. Upon administration, proparacaine stabilizes the neuronal membrane by binding to and inhibiting voltage-gated sodium channels. This inhibits the sodium ion influx required for the initiation and conduction of impulses within the neuronal cell, increases the threshold for electrical stimulation and results in a loss of sensation.

Proparacaine is a Local Anesthetic. The physiologic effect of proparacaine is by means of Local Anesthesia.

1 2D Structure

Prestwick3_000959

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(diethylamino)ethyl 3-amino-4-propoxybenzoate

2.1.2 InChI

InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3

2.1.3 InChI Key

KCLANYCVBBTKTO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCOC1=C(C=C(C=C1)C(=O)OCCN(CC)CC)N

2.2 Other Identifiers

2.2.1 UNII

B4OB0JHI1X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate

2. 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate Monohydrochloride

3. Ak-taine

4. Alcaine

5. Benzoic Acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl Ester

6. Benzoic Acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl Ester, Monohydrochloride*benzoic Acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl Ester, Monohydrochloride

7. Chibro-kerakain

8. Kracaine

9. Kainair

10. Minims Proxymetacaine Hydrochloride

11. Ocu-caine

12. Ophthaine

13. Ophthetic

14. Parcaine

15. Proparacaine Hcl

16. Proparacaine Hydrochloride

17. Proparakain-pos

18. Proxymetacaine

19. Proxymetacaine Hydrochloride

20. Proxymetacaine Monohydrochloride

21. Proxymethacaine

2.3.2 Depositor-Supplied Synonyms

1. Proxymetacaine

2. 499-67-2

3. 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate

4. Ophthaine

5. Proximetacainum

6. Paracaine

7. Alcaine

8. Prossimetacaina [dcit]

9. Ophthetic

10. Kainair

11. Proxymetacainum [inn-latin]

12. Proximetacaina [inn-spanish]

13. 3-amino-4-propoxybenzoic Acid 2-(diethylamino)ethyl Ester

14. Benzoic Acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl Ester

15. Chebi:8485

16. Proxymetacaine (inn)

17. B4ob0jhi1x

18. Prossimetacaina

19. Proximetacaina

20. Proxymetacainum

21. Proxymetacaine [inn]

22. Proxymetacaine [inn:ban]

23. Beta-(diethylamino)ethyl 4-n-propoxybenzoate

24. Ncgc00016991-03

25. Einecs 207-884-9

26. Unii-b4ob0jhi1x

27. Brn 2745891

28. Benzoic Acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl Ester, Hydrochloride

29. Prestwick0_000959

30. Prestwick1_000959

31. Prestwick2_000959

32. Prestwick3_000959

33. Proparacaine [mi]

34. Chembl1196

35. Proparacaine [vandf]

36. Schembl23334

37. Bspbio_000958

38. Mls006011856

39. Spbio_003107

40. Bpbio1_001054

41. Gtpl7283

42. Proxymetacaine [who-dd]

43. Dtxsid30198146

44. Hms3604h05

45. 2,5-dibromopyridine-3-boronicacid

46. Albb-025705

47. Bcp22476

48. Zinc1530762

49. Bbl003355

50. Bdbm50225500

51. Stk520616

52. Akos005457804

53. Db00807

54. Cas-1452000

55. Mrf-0000607

56. Ncgc00016991-01

57. Ncgc00016991-02

58. Ncgc00016991-06

59. Ncgc00016991-13

60. Ac-13440

61. Smr000857219

62. Sbi-0206900.p001

63. Ab00444123

64. Ft-0658833

65. Ft-0674059

66. .beta.-(diethylamino)ethyl 4-n-propoxybenzoate

67. A24938

68. C07383

69. D08448

70. Ab00444123_07

71. Ab00444123_08

72. Q600867

73. J-017667

74. Brd-k79116891-003-03-7

75. 3-amino-4-propoxy-,2-(diethylamino)ethyl Ester Benzoic Acid

76. 3-amino-4-propoxy-benzoic Acid 2-diethylamino-ethyl Ester, Hydrochloride

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₆N₂O₃
Molecular Weight	294.39 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	10
Exact Mass	294.19434270 g/mol
Monoisotopic Mass	294.19434270 g/mol
Topological Polar Surface Area	64.8 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	295
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used as a local (ophthalmic) anesthetic.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Proparacaine stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses thereby effecting local anesthetic action. More specifically, proparacaine appears to bind or antagonize the function of voltage gated sodium channels.

5.2 MeSH Pharmacological Classification

Anesthetics, Local

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

PROPARACAINE

5.3.2 FDA UNII

B4OB0JHI1X

5.3.3 Pharmacological Classes

Established Pharmacologic Class [EPC] - Local Anesthetic

5.4 ATC Code

S - Sensory organs

S01 - Ophthalmologicals

S01H - Local anesthetics

S01HA - Local anesthetics

S01HA04 - Proxymetacaine

5.5 Metabolism/Metabolites

Plasma

5.6 Mechanism of Action

The exact mechanism whereby proparacaine and other local anesthetics influence the permeability of the cell membrane is unknown; however, several studies indicate that local anesthetics may limit sodium ion permeability through the lipid layer of the nerve cell membrane. Proparacaine may alter epithelial sodium channels through interaction with channel protein residues. This limitation prevents the fundamental change necessary for the generation of the action potential.