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    Chemistry

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    Also known as: 94-24-6, Amethocaine, 2-(dimethylamino)ethyl 4-(butylamino)benzoate, Pontocaine, Dicaine, Laudocaine
    Molecular Formula
    C15H24N2O2
    Molecular Weight
    264.36  g/mol
    InChI Key
    GKCBAIGFKIBETG-UHFFFAOYSA-N
    FDA UNII
    0619F35CGV
    Tetracaine
    A potent local anesthetic of the ester type used for surface and spinal anesthesia.
    Tetracaine is an Ester Local Anesthetic. The physiologic effect of tetracaine is by means of Local Anesthesia.
    1 2D Structure

    Tetracaine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-(dimethylamino)ethyl 4-(butylamino)benzoate
    2.1.2 InChI
    InChI=1S/C15H24N2O2/c1-4-5-10-16-14-8-6-13(7-9-14)15(18)19-12-11-17(2)3/h6-9,16H,4-5,10-12H2,1-3H3
    2.1.3 InChI Key
    GKCBAIGFKIBETG-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    0619F35CGV
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Amethocaine

    2. Ametop

    3. Dicaine

    4. Hydrochloride, Tetrracaine

    5. Pantocaine

    6. Pontocaine

    7. Tetracaine Monohydrochloride

    8. Tetrakain

    9. Tetrracaine Hydrochloride

    2.3.2 Depositor-Supplied Synonyms

    1. 94-24-6

    2. Amethocaine

    3. 2-(dimethylamino)ethyl 4-(butylamino)benzoate

    4. Pontocaine

    5. Dicaine

    6. Laudocaine

    7. Metraspray

    8. Tetrakain

    9. Anetain

    10. Contralgin

    11. Meethobalm

    12. Mucaesthin

    13. Tetracaina

    14. Tetracainum

    15. Uromucaesthin

    16. Fissucain

    17. Intercain

    18. Medicaine

    19. Niphanoid

    20. Rexocaine

    21. Dicain

    22. Dikain

    23. Medihaler-tetracaine

    24. 2-(dimethylamino)ethyl P-(butylamino)benzoate

    25. P-butylaminobenzoyl-2-dimethylaminoethanol

    26. Benzoic Acid, 4-(butylamino)-, 2-(dimethylamino)ethyl Ester

    27. Diaethylaminoaethanol Ester Der P-butylaminobenzoesaeure

    28. 4-(butylamino)benzoic Acid 2-(dimethylamino)ethyl Ester

    29. Dimethylaminoethyl P-butyl-aminobenzoate

    30. Chebi:9468

    31. P-(butylamino)benzoic Acid, 2-(dimethylamino)ethyl Ester

    32. Mfcd00053787

    33. Chembl698

    34. Benzoic Acid, P-(butylamino)-, 2-(dimethylamino)ethyl Ester

    35. 2-dimethylaminoethylester Kyseliny P-butylaminobenzoove

    36. Tetracaine Base

    37. 0619f35cgv

    38. Butylocaine

    39. Tetrakain [czech]

    40. Tetracainum [inn-latin]

    41. Tetracaina [inn-spanish]

    42. P-(butylamino)benzoic Acid Beta-(dimethylamino)ethyl Ester

    43. Amethocaine (tn)

    44. Tetracaine (usp/inn)

    45. Ncgc00016049-02

    46. Cas-136-47-0

    47. Einecs 202-316-6

    48. Brn 2216051

    49. Landocaine

    50. Tetracaine [usp:inn:ban]

    51. Unii-0619f35cgv

    52. Amethocaine Hcl

    53. 2-dimethylaminoethylester Kyseliny P-butylaminobenzoove [czech]

    54. Diaethylaminoaethanol Ester Der P-butylaminobenzoesaeure [german]

    55. Te4

    56. Spectrum_001032

    57. Pantocaine (salt/mix)

    58. Tetracaine [inn]

    59. 100311-22-6

    60. Prestwick0_000571

    61. Prestwick1_000571

    62. Prestwick2_000571

    63. Prestwick3_000571

    64. Spectrum2_001328

    65. Spectrum3_000562

    66. Spectrum4_000351

    67. Spectrum5_001072

    68. Lopac-t-7508

    69. Tetracaine [vandf]

    70. Epitope Id:174843

    71. Tetracaine [mart.]

    72. Tetracaine [usp-rs]

    73. Tetracaine [who-dd]

    74. Lopac0_001211

    75. Schembl34714

    76. Bspbio_000382

    77. Bspbio_001944

    78. Kbiogr_000781

    79. Kbioss_001512

    80. 4-14-00-01172 (beilstein Handbook Reference)

    81. Divk1c_000607

    82. Spbio_001455

    83. Spbio_002601

    84. Bpbio1_000422

    85. Tetracaine [green Book]

    86. Tetracaine, >=98% (tlc)

    87. Dtxsid1043883

    88. Tetracaine [orange Book]

    89. Kbio1_000607

    90. Kbio2_001512

    91. Kbio2_004080

    92. Kbio2_006648

    93. Kbio3_001444

    94. Tetracaine [ep Monograph]

    95. Ninds_000607

    96. Synera Component Tetracaine

    97. Bcpp000048

    98. Tetracaine [usp Monograph]

    99. Act04765

    100. Albb-025902

    101. Bcp04777

    102. Hy-a0079

    103. Zinc1530811

    104. Bdbm50017659

    105. Stl483844

    106. Tetracaine Component Of Synera

    107. Akos015889234

    108. Ac-3480

    109. Ccg-205285

    110. Db09085

    111. Sdccgsbi-0051178.p005

    112. Idi1_000607

    113. Ncgc00016049-01

    114. Ncgc00016049-03

    115. Ncgc00016049-04

    116. Ncgc00016049-14

    117. Ncgc00162367-01

    118. As-81743

    119. Sy066710

    120. Bcp0726000001

    121. Sbi-0051178.p004

    122. Ab00053549

    123. Ft-0656378

    124. T2789

    125. Tetracaine, Meets Usp Testing Specifications

    126. .beta.-dimethylaminoethyl P-butylaminobenzoate

    127. 2-(dimethylamino)ethyl4-(n-butylamino)benzoate

    128. C07526

    129. D00551

    130. 2-(dimethylamino)ethyl 4-(butylamino)benzoate #

    131. Ab00053549-11

    132. Ab00053549_12

    133. Ab00053549_13

    134. Q419608

    135. Q-201805

    136. Brd-k45071273-003-05-8

    137. Brd-k45071273-003-15-7

    138. Tetracaine, United States Pharmacopeia (usp) Reference Standard

    139. Benzoic Acid, 4-(butylamino)-, 2-(dimethylamino)ethyl Ester ,hydrochloride

    140. Benzoic Acid,4-butylamino,2-dimethylaminoethyl Ester Pantocain Base

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 264.36 g/mol
    Molecular Formula C15H24N2O2
    XLogP33.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count9
    Exact Mass264.183778013 g/mol
    Monoisotopic Mass264.183778013 g/mol
    Topological Polar Surface Area41.6 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity249
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Ophthalmic tetracaine is indicated for the for procedures requiring a rapid and short- acting topical ophthalmic anesthetic. The combination lidocaine and tetracaine patch is indicated for local dermal analgesia for superficial dermatological procedures and superficial venous access. The combination lidocaine and tetracaine cream is intended to provide topical local analgesia for superficial dermatological procedures.

    FDA Label

    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 Active Moiety
    TETRACAINE
    5.2.2 FDA UNII
    0619F35CGV
    5.2.3 Pharmacological Classes
    Esters [CS]; Local Anesthesia [PE]; Ester Local Anesthetic [EPC]
    5.3 ATC Code

    S01HA03

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    C - Cardiovascular system

    C05 - Vasoprotectives

    C05A - Agents for treatment of hemorrhoids and anal fissures for topical use

    C05AD - Local anesthetics

    C05AD02 - Tetracaine

    D - Dermatologicals

    D04 - Antipruritics, incl. antihistamines, anesthetics, etc.

    D04A - Antipruritics, incl. antihistamines, anesthetics, etc.

    D04AB - Anesthetics for topical use

    D04AB06 - Tetracaine

    N - Nervous system

    N01 - Anesthetics

    N01B - Anesthetics, local

    N01BA - Esters of aminobenzoic acid

    N01BA03 - Tetracaine

    S - Sensory organs

    S01 - Ophthalmologicals

    S01H - Local anesthetics

    S01HA - Local anesthetics

    S01HA03 - Tetracaine

    5.4 Absorption, Distribution and Excretion

    Absorption

    Systemic absorption of anaesthetic from the combination cream is directly related to the duration and surface area of application. Although peak plasma concentrations for lidocaine were measured, plasma levels for tetracaine could not be determined due to low levels (<0.9 ng/mL)

    Volume of Distribution

    Tetracaine is rapidly hydrolyzed in the plasma; therefore, volume of distribution could not be determined.

    Clearance

    Tetracaine is hydrolyzed rapidly in the plasma; therefore, clearance has not been determined.

    5.5 Metabolism/Metabolites

    Tetracaine is rapidly hydrolyzed by plasma esterases to the following primary metabolites: para-aminobenzoic acid and diethylaminoethanol. The activity of both metabolites is unspecified.

    5.6 Biological Half-Life

    Tetracaine is hydrolyzed rapidly in the plasma; therefore, half-life has not been determined.

    5.7 Mechanism of Action

    Tetracaine is an ester-type anesthetic and produces local anesthesia by blocking the sodium ion channels involved in initiation and conduction of neuronal impulses.

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    11-Jan-2021
    16-Nov-2024
    KGS
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    Average Price (USD/KGS)

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - PATCH;TOPICAL - 70MG;70MG

    USFDA APPLICATION NUMBER - 21623

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    DOSAGE - CREAM;TOPICAL - 7%;7%

    USFDA APPLICATION NUMBER - 21717

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