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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
    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

    Proparacaine hydrochloride

    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 Weight 330.8 g/mol
    Molecular Formula C16H27ClN2O3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count10
    Exact Mass330.1710204 g/mol
    Monoisotopic Mass330.1710204 g/mol
    Topological Polar Surface Area64.8 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity295
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameProparacaine hydrochloride
    Drug LabelALCAINE (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 IngredientProparacaine hydrochloride
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.5%
    Market StatusPrescription
    CompanyBausch And Lomb; Akorn

    2 of 2  
    Drug NameProparacaine hydrochloride
    Drug LabelALCAINE (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 IngredientProparacaine hydrochloride
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.5%
    Market StatusPrescription
    CompanyBausch 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]

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