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DSSTox_CID_28948

DSSTox_CID_28948

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Also known as: 5875-06-9, Proparacaine hcl, Proxymetacaine hydrochloride, Alcaine, 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate hydrochloride, Proparacaine, hcl

Molecular Formula

C₁₆H₂₇ClN₂O₃

Molecular Weight

330.8 g/mol

InChI Key

BFUUJUGQJUTPAF-UHFFFAOYSA-N

FDA UNII

U96OL57GOY

Proparacaine Hydrochloride is the hydrochloride salt form of proparacaine, a benzoic acid derivative with local anesthetic property. Proparacaine hydrochloride stabilizes the neuronal membrane by binding to and inhibiting voltage-gated sodium channels, thereby inhibiting sodium ion influx required for the initiation and conduction of impulses within the neuronal cell, and resulting in a loss of sensation.

1 2D Structure

DSSTox_CID_28948

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C16H26N2O3.ClH/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;1H

2.1.3 InChI Key

BFUUJUGQJUTPAF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

U96OL57GOY

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

16. Proparacaine Hcl

17. Proparakain-pos

18. Proxymetacaine

19. Proxymetacaine Hydrochloride

20. Proxymetacaine Monohydrochloride

21. Proxymethacaine

2.3.2 Depositor-Supplied Synonyms

1. 5875-06-9

2. Proparacaine Hcl

3. Proxymetacaine Hydrochloride

4. Alcaine

5. 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate Hydrochloride

6. Proparacaine, Hcl

7. Ophthaine

8. Ak-taine

9. Proparacaine (hydrochloride)

10. Kainair

11. Ophthetic

12. 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate;hydrochloride

13. Nsc-759896

14. U96ol57goy

15. Dsstox_cid_28948

16. Dsstox_rid_83213

17. Dsstox_gsid_49022

18. Proparacaine Hydrochloride (usp)

19. Proparacaine Hydrochloride [usp]

20. Ophthain

21. 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate Monohydrochloride

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

23. Smr000875264

24. Cas-5875-06-9

25. Ncgc00016991-03

26. Mfcd00083467

27. Keracaine

28. Chibro-heracaine

29. Ophthetic (tn)

30. Alcaine (tn)

31. Proparacainehydrochloride

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

33. Unii-u96ol57goy

34. Schembl93880

35. Mls001333067

36. Mls001333068

37. Mls002154072

38. Chembl1200464

39. Dtxsid0049022

40. 2-diethylaminoethyl 3-amino-4-propoxybenzoate Hydrochloride

41. Hms1570p20

42. Pharmakon1600-01505688

43. Einecs 227-541-7

44. Tox21_113547

45. Nsc759896

46. S1828

47. Akos015844989

48. Tox21_113547_1

49. Ac-3399

50. Ccg-213513

51. Ks-5058

52. Nc00586

53. Nsc 759896

54. Proparacaine Hydrochloride [mi]

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

56. Ncgc00016991-05

57. Hy-66012

58. Proparacaine Hydrochloride [vandf]

59. Proxymetacaine Hydrochloride, Proparacaine

60. Proparacaine Hydrochloride [usp-rs]

61. Proxymetacaine Hydrochloride [mart.]

62. P2156

63. Proxymetacaine Hydrochloride [who-dd]

64. Sw197338-3

65. Proparacaine Hydrochloride, Analytical Standard

66. C75748

67. D02098

68. Proparacaine Hydrochloride [green Book]

69. Proparacaine Hydrochloride [orange Book]

70. 875p069

71. A832009

72. Proparacaine Hydrochloride [usp Monograph]

73. 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate Hcl

74. Sr-05000001759-3

75. Q27290947

76. 2-diethylaminoethyl3-amino-4-propoxy-benzoatehydrochloride

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

78. Beta-(diethylamino)ethyl 3-amino-4-n-propoxybenzoate Hydrochloride

79. 3-amino-4-propoxybenzoic Acid 2-(diethylamino)ethyl Ester Hydrochloride

80. 2-(diethylamino)ethyl 3-amino-4-propoxy-benzoate Hydrochloride;proparacaine Hcl

81. Proparacaine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₇ClN₂O₃
Molecular Weight	330.8 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	10
Exact Mass	330.1710204 g/mol
Monoisotopic Mass	330.1710204 g/mol
Topological Polar Surface Area	64.8 Å²
Heavy Atom Count	22
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	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Proparacaine hydrochloride
Drug Label	ALCAINE (proparacaine hydrochloride ophthalmic solution, USP) 0.5% is a topical local anesthetic for ophthalmic use. The active ingredient is represented by the structural formula:Established name:Proparacaine Hydrochloride Chemical name:Benzoic ac...
Active Ingredient	Proparacaine hydrochloride
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%
Market Status	Prescription
Company	Bausch And Lomb; Akorn

2 of 2
Drug Name	Proparacaine hydrochloride
Drug Label	ALCAINE (proparacaine hydrochloride ophthalmic solution, USP) 0.5% is a topical local anesthetic for ophthalmic use. The active ingredient is represented by the structural formula:Established name:Proparacaine Hydrochloride Chemical name:Benzoic ac...
Active Ingredient	Proparacaine hydrochloride
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%
Market Status	Prescription
Company	Bausch And Lomb; Akorn

5 Pharmacology and Biochemistry

5.1 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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Local Anesthetic [EPC]; Local Anesthesia [PE]