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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.


API Reference Price

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06-Jan-2021
26-Aug-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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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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