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Technical details about Prestwick3_000058, learn more about the structure, uses, toxicity, action, side effects and more

Prestwick3_000058

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

10 Suppliers, 1 JDMF, 2 EU WC, 8 Listed Suppliers

PRICE INFORMATION

API Reference Price, API Exports, API Imports

DOSSIERs // Finished Dosage Forms

5 Dossiers, 2 South Africa, 3 Listed Dossiers

MARKET PLACE

15 APIs

15 APIs

Prestwick3_000058
Chemistry
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Also known as: Oxetacaine, 126-27-2, Oxethacaine, Mucaine, Oxaethacainum, Betalgil

Molecular Formula

C₂₈H₄₁N₃O₃

Molecular Weight

467.6 g/mol

InChI Key

FTLDJPRFCGDUFH-UHFFFAOYSA-N

FDA UNII

IP8QT76V17

Oxetacaine, also called oxethazaince, is a potent surface analgesic with the molecular formula N, N-bis-(N-methyl-N-phenyl-t-butyl-acetamide)-beta-hydroxyethylamine that conserves its unionized form at low pH levels. Its actions have shown to relieve dysphagia, relieve pain due to reflux, chronic gastritis, and duodenal ulcer. Oxetacaine is approved by Health Canada since 1995 for its use as an antacid combination in over-the-counter preparations. It is also in the list of approved derivatives of herbal products by the EMA.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2-hydroxyethyl-[2-[methyl-(2-methyl-1-phenylpropan-2-yl)amino]-2-oxoethyl]amino]-N-methyl-N-(2-methyl-1-phenylpropan-2-yl)acetamide

2.1.2 InChI

InChI=1S/C28H41N3O3/c1-27(2,19-23-13-9-7-10-14-23)29(5)25(33)21-31(17-18-32)22-26(34)30(6)28(3,4)20-24-15-11-8-12-16-24/h7-16,32H,17-22H2,1-6H3

2.1.3 InChI Key

FTLDJPRFCGDUFH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(CC1=CC=CC=C1)N(C)C(=O)CN(CCO)CC(=O)N(C)C(C)(C)CC2=CC=CC=C2

2.2 Other Identifiers

2.2.1 UNII

IP8QT76V17

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2,2'-((2-hydroxyethyl)imino)bis(n-alpha,alpha-dimethylphenethyl)-n-methylacetamide

2. Mucaine

3. Muthesa

4. Oxaine

5. Oxetacain

6. Oxethazaine Hydrochloride

7. Oxethazaine Monohydrochloride

8. Oxethazine

9. Robercain R

10. Tepilta

2.3.2 Depositor-Supplied Synonyms

1. Oxetacaine

2. 126-27-2

3. Oxethacaine

4. Mucaine

5. Oxaethacainum

6. Betalgil

7. Strocain

8. Emoren

9. Oxethazine

10. Oxetacaine [inn]

11. Wy-806

12. Acetamide, 2,2'-((2-hydroxyethyl)imino)bis(n-(1,1-dimethyl-2-phenylethyl)-n-methyl-

13. Nsc-758444

14. Chembl127592

15. Ip8qt76v17

16. 2-[2-hydroxyethyl-[2-[methyl-(2-methyl-1-phenylpropan-2-yl)amino]-2-oxoethyl]amino]-n-methyl-n-(2-methyl-1-phenylpropan-2-yl)acetamide

17. Chebi:31947

18. Oxetacaine (inn)

19. 2,2'-((2-hydroxyethyl)imino)bis(n-(1,1-dimethyl-2-phenylethyl)-n-methylacetamide)

20. Acetamide, 2,2'-[(2-hydroxyethyl)imino]bis[n-(1,1-dimethyl-2-phenylethyl)-n-methyl-

21. Ncgc00016382-01

22. Cas-126-27-2

23. Dsstox_cid_5818

24. Dsstox_rid_77936

25. Dsstox_gsid_25818

26. Oxethacaina [italian]

27. Milzine

28. Oxetacainum [inn-latin]

29. Oxetacaina [inn-spanish]

30. Ccris 4692

31. Sr-05000001851

32. Einecs 204-780-5

33. Fh 099

34. Wy 806

35. Oxethazaine [usan:jan]

36. Brn 2404063

37. Unii-ip8qt76v17

38. Prestwick_767

39. Spectrum_001657

40. 2-di(n-methyl-n-phenyl-tert-butyl-carbamoylmethyl)aminoethanol

41. Oxethazaine [mi]

42. Prestwick0_000058

43. Prestwick1_000058

44. Prestwick2_000058

45. Prestwick3_000058

46. Spectrum2_001987

47. Spectrum3_001751

48. Spectrum4_000202

49. Spectrum5_001269

50. Oxethazaine [jan]

51. N,n-bis(n-methyl-n-phenyl-tert-butylacetamido)-beta-hydroxyethylamine

52. Oxethazaine [usan]

53. Cid_4621

54. Oxetacaine [mart.]

55. 2,2'-((2-hydroxyethyl)imino)bis(n-(alpha,alpha-dimethylphenethyl)-n-methylacetamide)

56. Oxetacaine [who-dd]

57. Oxethazaine (jp17/usan)

58. Schembl24489

59. Bspbio_000215

60. Bspbio_003482

61. Kbiogr_000803

62. Kbioss_002137

63. 4-12-00-02822 (beilstein Handbook Reference)

64. Mls002154188

65. Divk1c_000715

66. Spectrum1503279

67. Spbio_002136

68. Spbio_002173

69. Bpbio1_000237

70. Oxethazaine, Analytical Standard

71. Dtxsid0025818

72. Hms502d17

73. Kbio1_000715

74. Kbio2_002137

75. Kbio2_004705

76. Kbio2_007273

77. Kbio3_002702

78. Ninds_000715

79. Hms1568k17

80. Hms1922a04

81. Hms2093c15

82. Hms2095k17

83. Hms2236a03

84. Hms3370m13

85. Hms3712k17

86. Hms3885p21

87. Pharmakon1600-01503279

88. Bcp07626

89. Hy-b0955

90. Zinc3874585

91. Tox21_110407

92. Bdbm50017672

93. Ccg-39525

94. Nsc758444

95. Akos024284189

96. Tox21_110407_1

97. Cs-4432

98. Db12532

99. Nsc 758444

100. Acetamide, 2,2'-((2-hydroxyethyl)imino)bis(n-(alpha,alpha-dimethylphenethyl)-n-methyl-

101. Idi1_000715

102. Ncgc00016382-02

103. Ncgc00016382-03

104. Ncgc00016382-04

105. Ncgc00016382-07

106. Ncgc00016382-09

107. Ncgc00095039-01

108. Ncgc00095039-02

109. Ncgc00095039-03

110. N-(1,1-dimethyl-2-phenyl-ethyl)-2-[[2-[(1,1-dimethyl-2-phenyl-ethyl)-methyl-amino]-2-oxo-ethyl]-(2-hydroxyethyl)amino]-n-methyl-acetamide

111. Smr001233479

112. Sbi-0051816.p002

113. Db-041818

114. Ab00052348

115. Ft-0603332

116. Sw196906-3

117. D01152

118. Ab00052348_08

119. Ab00052348_09

120. 126o272

121. J-005353

122. Q2412605

123. Sr-05000001851-1

124. Sr-05000001851-3

125. Brd-k56940463-001-05-4

126. Brd-k56940463-001-08-8

127. 2-hydroxyethyliminobis(n-[alpha,alpha-dimethylphenethyl]-n-methylacetamide)

128. 2,2'-(2-hydroxyethylazanediyl)bis(n-methyl-n-(2-methyl-1-phenylpropan-2-yl)acetamide)

129. 2,2'-((2-hydroxyethyl)imino)bis(n-(.alpha.,.alpha.-dimethylphenethyl)-n-methylacetamide)

130. N-(1,1-dimethyl-2-phenyl-ethyl)-2-[{[(1,1-dimethyl-2-phenyl-ethyl)-methyl-carbamoyl]-methyl}-(2-hydroxy-ethyl)-amino]-n-methyl-acetamide

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₈H₄₁N₃O₃
Molecular Weight	467.6 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	12
Exact Mass	467.31479218 g/mol
Monoisotopic Mass	467.31479218 g/mol
Topological Polar Surface Area	64.1 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	585
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

Oxetacaine is available as an over-the-counter antacid and it is used to alleviate pain associated with gastritis, peptic ulcer disease, heartburn, esophagitis, hiatus hernia, and anorexia.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Oxetacaine improves common gastrointestinal symptoms. Oxetacaine is part of the anesthetic antacids which increase the gastric pH while providing relief from pain for a longer period of duration at a lower dosage. This property has been reported to relieve the symptoms of hyperacidity. Oxetacaine is reported to produce a reversible loss of sensation and to provide a prompt and prolonged relief of pain. In vitro, oxetacaine was showed to produce an antispasmodic action on the smooth muscle and block the action of serotonin. The local efficacy of oxetacaine has been proven to be 2000 times more potent than lignocaine and 500 times more potent than cocaine. Its anesthetic action produces the loss of sensation which can be explained by its inhibitory activity against the nerve impulses and de decrease in permeability of the cell membrane.

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 ATC Code

C - Cardiovascular system

C05 - Vasoprotectives

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

C05AD - Local anesthetics

C05AD06 - Oxetacaine

5.4 Absorption, Distribution and Excretion

Absorption

A peak plasma concentration of oxetacaine of approximately 20 ng/ml is attained about one hour after oral administration. LEss than 1/3 of the administered dose is absorbed as it undergoes extensive metabolism.

Route of Elimination

Less than 0.1% of the amdinistered dose is recovered in urine within 24 hours in the form of unchanged oxetacaine or its metabolites.

Volume of Distribution

This pharmacokinetic property has not been studied.

Clearance

This pharmacokinetic property has not been studied.

5.5 Metabolism/Metabolites

Oxetacaine is rapidly and extensively metabolized hepatically. After metabolism, there is a formation of primary metabolites such as beta-hydroxy-mephentermine and beta-hydroxy-phentermine. The major metabolites are found in the plasma in insignificant amounts.

5.6 Biological Half-Life

Oxetacaine presents a very short half-life of approximately one hour.

5.7 Mechanism of Action

Oxetacaine inhibits gastric acid secretion by suppressing gastrin secretion. Moreover, oxetacaine exerts a local anesthetic effect on the gastric mucosa. This potent local anesthetic effect of oxetacaine may be explained by its unique chemical characteristics in which, as a weak base, it is relatively non-ionized in acidic solutions whereas its hydrochloride salt is soluble in organic solvents and it can penetrate cell membranes. Oxetacaine diminishes the conduction of sensory nerve impulses near the application site which in order reduces the permeability of the cell membrane to sodium ions. This activity is performed by the incorporation of the unionized form into the cell membrane.

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