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    Butamben

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: Butamben, 94-25-7, Butesin, Butyl aminobenzoate, Butoform, Butylcaine
    Molecular Formula
    C11H15NO2
    Molecular Weight
    193.24  g/mol
    InChI Key
    IUWVALYLNVXWKX-UHFFFAOYSA-N
    FDA UNII
    EFW857872Q
    Butamben is a local anesthetic in the form of n-butyl-p-aminobenzoate. Its structure corresponds to the standard molecule of a hydrophilic and hydrophobic domain separated by an intermediate ester found in most of the local anesthetics. Due to its very low water solubility, butamben was considered of low usability as it is only suitable to be used as a topical anesthesia. This belief changed with the introduction of epidural suspensions of butamben. All butamben-containing products were removed from the market under the belief that it is unsafe or ineffective.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    butyl 4-aminobenzoate
    2.1.2 InChI
    InChI=1S/C11H15NO2/c1-2-3-8-14-11(13)9-4-6-10(12)7-5-9/h4-7H,2-3,8,12H2,1H3
    2.1.3 InChI Key
    IUWVALYLNVXWKX-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCOC(=O)C1=CC=C(C=C1)N
    2.2 Other Identifiers
    2.2.1 UNII
    EFW857872Q
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Butamben

    2. Butamben Picrate

    3. Butanylcaine

    4. Butesin

    5. Butyl Aminobenzoate

    6. Butylcaine

    7. N-butyl-p-aminobenzoate

    8. Zyljectin

    2.3.2 Depositor-Supplied Synonyms

    1. Butamben

    2. 94-25-7

    3. Butesin

    4. Butyl Aminobenzoate

    5. Butoform

    6. Butylcaine

    7. Butesine

    8. Planoform

    9. Scuroform

    10. Scuroforme

    11. Butyl P-aminobenzoate

    12. 4-(butoxycarbonyl)aniline

    13. Butyl Keloform

    14. Benzoic Acid, 4-amino-, Butyl Ester

    15. N-butyl P-aminobenzoate

    16. P-aminobenzoic Acid Butyl Ester

    17. 4-aminobenzoic Acid Butyl Ester

    18. 4-aminobenzoic Acid N-butyl Ester

    19. N-butyl-p-aminobenzoate

    20. Butyl Paba

    21. Benzoic Acid, P-amino-, Butyl Ester

    22. Mfcd00017112

    23. Nsc 128464

    24. 4-amino Butylbenzoate

    25. P-aminobenzoic Acid, Butyl Ester

    26. Butylester Kyseliny P-aminobenzoove

    27. 4-aminobenzoic Acid Butyl

    28. Nsc-128464

    29. Mls000028721

    30. Chebi:3231

    31. Efw857872q

    32. Nsc128464

    33. Cas-94-25-7

    34. Ncgc00016353-03

    35. Smr000059139

    36. Dsstox_cid_2417

    37. Dsstox_rid_76583

    38. Dsstox_gsid_22417

    39. Butamben [usan]

    40. Butsein

    41. Ccris 5891

    42. Hsdb 4245

    43. Butamben [usan:usp]

    44. Sr-01000721933

    45. Einecs 202-317-1

    46. Brn 1211465

    47. Butoforme

    48. Unii-efw857872q

    49. Ai3-02284

    50. Butylester Kyseliny P-aminobenzoove [czech]

    51. Butamben (usp)

    52. Prestwick_994

    53. Butesin (tn)

    54. Butyl -4-aminobenzoate

    55. Spectrum_000025

    56. Butamben [hsdb]

    57. N-butyl 4-aminobenzoate

    58. Opera_id_633

    59. Specplus_000829

    60. Butamben [mi]

    61. Butamben [vandf]

    62. Prestwick0_000761

    63. Prestwick1_000761

    64. Prestwick2_000761

    65. Prestwick3_000761

    66. Spectrum2_000850

    67. Spectrum3_001848

    68. Spectrum4_000832

    69. Spectrum5_001496

    70. Butamben [usp-rs]

    71. Butyl Paba [inci]

    72. Wln: Zr Dvo4

    73. Schembl81735

    74. Bspbio_000802

    75. Bspbio_003236

    76. Kbiogr_001403

    77. Kbioss_000385

    78. Mls002303044

    79. Bidd:er0674

    80. Divk1c_000838

    81. Divk1c_006925

    82. Spectrum1500767

    83. Spbio_000839

    84. Spbio_002741

    85. Bpbio1_000884

    86. Chembl127516

    87. Butamben [usp Monograph]

    88. Dtxsid7022417

    89. Hms502j20

    90. Kbio1_000838

    91. Kbio1_001869

    92. Kbio2_000385

    93. Kbio2_002953

    94. Kbio2_005521

    95. Kbio3_002736

    96. Ninds_000838

    97. P-aminobenzoic Acid N-butyl Ester

    98. Abbott-34842 Free Base

    99. Hms1570i04

    100. Hms1921g20

    101. Hms2092k06

    102. Hms2097i04

    103. Hms2234m07

    104. Hms3372c17

    105. Hms3714i04

    106. Hms3885n08

    107. Pharmakon1600-01500767

    108. Butyl Aminobenzoate [mart.]

    109. Hy-b1430

    110. Zinc1530937

    111. Tox21_110392

    112. Tox21_200378

    113. Butyl Aminobenzoate [who-dd]

    114. Ccg-40317

    115. Nsc757433

    116. S4583

    117. Stl169355

    118. Akos000119787

    119. Tox21_110392_1

    120. Cs-4822

    121. Db11148

    122. Nsc-757433

    123. Idi1_000838

    124. Ncgc00016353-01

    125. Ncgc00016353-02

    126. Ncgc00016353-04

    127. Ncgc00016353-05

    128. Ncgc00016353-06

    129. Ncgc00016353-08

    130. Ncgc00091154-01

    131. Ncgc00091154-02

    132. Ncgc00091154-03

    133. Ncgc00091154-04

    134. Ncgc00257932-01

    135. Ac-13349

    136. Ds-13802

    137. Para-aminobenzoic Acid Butyl Ester

    138. Sy051932

    139. Sbi-0051887.p002

    140. Db-029553

    141. A0270

    142. Ab00052407

    143. Ft-0617559

    144. A16090

    145. C07875

    146. D00730

    147. W16695

    148. Ab00052407_12

    149. Ae-641/05573061

    150. Q-200433

    151. Q5002348

    152. Sr-01000721933-2

    153. Sr-01000721933-3

    154. Brd-k27217864-001-04-1

    155. Brd-k27217864-001-05-8

    156. Brd-k27217864-001-15-7

    157. Z57126994

    158. F2190-0449

    159. Butamben, United States Pharmacopeia (usp) Reference Standard

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 193.24 g/mol
    Molecular Formula C11H15NO2
    XLogP32.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count5
    Exact Mass193.110278721 g/mol
    Monoisotopic Mass193.110278721 g/mol
    Topological Polar Surface Area52.3 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity174
    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 Therapeutic Uses

    Anesthetics, Local

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    ... POORLY SOL IN WATER &, CONSEQUENTLY, TOO SLOWLY ABSORBED TO BE TOXIC. THEY CAN BE APPLIED DIRECTLY TO WOUNDS & ULCERATED SURFACES WHERE THEY REMAIN LOCALIZED FOR LONG PERIODS OF TIME ... ACCOUNTS FOR SUSTAINED ANESTHETIC ACTION. ... MOST IMPORTANT MEMBERS OF SERIES ARE ... BUTAMBEN, USP (BUTYL AMINOBENZOATE, BUTESIN).

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 310

    MEDICATION (VET): TOPICALLY, AS SPRAY OR IN OINTMENTS (1-2%). ...PARENTERAL USE IN OIL HAS PROVIDED ANESTHESIA FOR UP TO 1 OR 2 DAYS & IS OCCASIONALLY USED IN DEEP PERIANAL INJECTIONS (OR WITH PROCAINE BASE & BENZYL ALC) WHERE PROLONGED PROTECTION AGAINST STRAINING IS DESIRED.

    Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 55

    Topical anesthetics are indicated to relieve pain, pruritus, and inflammation associated with minor skin disorders, including: burns, minor, including sunburn; bites (or stings), insect; dermatitis, contact, including poison ivy, poison oak, or poison sumac; wounds, minor such as cuts and scratches. /Included in US product labeling; Topical anesthetics/

    USP. Convention. USPDI - Drug Information for the Health Care Professional. 19th ed. Volume I.Micromedex, Inc. Englewood, CO., 1999. Content Prepared by the U.S. Pharmacopieal Convention, Inc., p. 155

    4.2 Drug Indication

    Butamben was indicated for the treatment of chronic pain due to its long-duration effect. It is also indicated as a surface anesthetic for skin a mucous membrane and for the relief of pain and pruritus associated with anorectal disorders.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Butamben has been shown to selectively inhibit dorsal root pain signal transmission for periods of months when administered as epidural suspensions. The effect of butamben is not related to any significant loss of motor function which indicates that it targets specifically the pain-sensing C fibers of the dorsal root. When administered topically, butamben produced anesthesia by accumulating in the nerve cell membrane causing it to expand and lose its ability to depolarize and blocking the impulse transmission.

    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 Absorption, Distribution and Excretion

    Absorption

    When butamben is administered epidurally in a suspension form, the physical characteristics of butamben allow a very slow release. When administered topically, butamben is also reported to have a very low systemic absorption which allows for a longer duration of action.

    Route of Elimination

    The metabolites found in plasma after cholinesterase processing are disposed of in the urine.

    Volume of Distribution

    This pharmacokinetic property has not been determined.

    Clearance

    Clearance is flow-limited and it highly depends on the state of protein-bound form.

    5.4 Metabolism/Metabolites

    The metabolic pathway of butamben follows the same pattern of other local anesthetics and it is driven mainly by the hydrolysis via cholinesterase for the formation of inert metabolites.

    5.5 Biological Half-Life

    The effective half-life of unencapsulated butamben is registered to be of 90 minutes. Some efforts were made to prepare D, L-lactic acid capsules which increased the half-life of butamben to even 400 hours.

    5.6 Mechanism of Action

    Butamben acts by inhibiting the voltage-gated calcium channels in dorsal root ganglion neurons. The modification in this channels is thought to cause a disturbance of the channel kinetics acceleration. It is reported as well that butamben is an inhibitor of the sodium channels and a delayed rectifier of potassium currents. All the effects of butamben are performed in the root ganglion neurons which suggests that the related anesthetic effect may be caused by the reduced electrical excitability.

    ...ACTION IS TO INTERFERE WITH INITIATION & TRANSMISSION OF NERVE IMPULSE. PRESENT THEORY HOLDS THAT LOCAL ANESTHETICS PREVENT DEPOLARIZATION OF NERVE MEMBRANE &, HENCE, PROPAGATION OF IMPULSE. ...THOUGHT TO BE DUE TO INTERFERENCE WITH MUTUAL EXCHANGE OF SODIUM & POTASSIUM IONS ACROSS MEMBRANE. /LOCAL ANESTHETICS/

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 987