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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
    Oxethazaine
    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

    Oxethazaine

    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 Weight 467.6 g/mol
    Molecular Formula C28H41N3O3
    XLogP33.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count12
    Exact Mass467.31479218 g/mol
    Monoisotopic Mass467.31479218 g/mol
    Topological Polar Surface Area64.1 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity585
    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

    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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    Oxetacaine (1 kg) API needed in India [ENA21360]
    A company that focuses on the research, development and manufacturing of OSDs, injectables, liquids & semi-solids is looking for suppliers of Oxetacaine (1 kg) API for development purposes. The suppliers must support this enquiry with CoA.
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    Oxetacaine API needed in Turkey [ENA20480]
    A company that focuses on development and manufacturing of various finished formulations including solid, liquid and soft gel dosage forms is looking for suppliers of Oxetacaine API for development purposes. The suppliers must support this enquiry with CEP, DMF, GMP & CoA.
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    BP Grade Oxetacaine (4 MT) API needed in India [ENA19192]
    A leading research-based biopharmaceutical company that deals in drug development, manufacturing & marketing is looking for suppliers of BP Grade Oxetacaine (4 MT) API for commercial Purposes. The suppliers must support this enquiry with CoA.
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    Various APIs needed in India [ENA17095]
    A company that deals in various pharmaceutical products like injections, syrups & hygiene products is looking for suppliers of Various APIs for commercial purposes. The suppliers must support this enquiry with CoA. 1. IP Grade Ciprofloxacin HCl (25 kg) API 2. Esomeprazole Magnesium Trihydrate (15 kg) API 3. BP Grade Oxetacaine (5 kg) API
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    BP Grade Oxetacaine (5 kg) API needed in India [ENA16141]
    A company that deals in various pharmaceutical products like injections, syrups & hygiene products is looking for suppliers of BP Grade Oxetacaine (5 kg) API for commercial purposes. The suppliers must support this enquiry with CoA.
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    Oxethazaine API needed in Brazil [ENA13058]
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    Various APIs needed in Bangladesh [ENA11299]
    A pharmaceutical company that manufactures more than 500 products in different dosage forms covering broader therapeutic categories which include anti-infective, cardiovascular, antidiabetics, gastrointestinal, CNS & respiratory disease is looking for suppliers of Various APIs for development purpose. The required quantity is 10 kg for each. The suppliers must support this enquiry with CoA. 1. Estetrol API 2. Calcium Oxytetracycline API 3. Oxetacaine API 4. Tepotinib API 5. Efonidipine API
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    Oxethazaine (50 kg) API needed in Taiwan [ENA08892]
    A pharmaceutical company that manufactures various finished dosage formulations is looking for suppliers of Oxethazaine (50 kg) API. The supplier must support this enquiry with GMP & Taiwan-DMF.
    26 Oct 2020

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    26 Oct 2020

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    26 Oct 2020

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    Oxetacaine (25 kg) API needed in India [ENA07541]
    Chennai Pharma, a company based in India is looking for suppliers of Oxetacaine (25 kg) API. Interested suppliers can contact them via their email: arwindm.cp@gmail.com.
    11 Jun 2020

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    11 Jun 2020

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    11 Jun 2020

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    IP/BP grade Oxetacaine (MOQ) API needed in India [ENA06198]
    A platform for strategic and regulatory based product development services is looking for suppliers of IP/BP grade Oxetacaine (MOQ) API.
    02 Jan 2020

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    02 Jan 2020

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    02 Jan 2020

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