Peringatan Keamanan

In studies, the most common effect was related to the generation of a prolonged effect. It was also shown in preclinical trials to produce tissue necrosis and neuritis. The LD50 of butamben is registered to be of 67 mg/kg.T175

Butamben

DB11148

small molecule approved withdrawn

Deskripsi

Butamben is a local anesthetic in the form of n-butyl-p-aminobenzoate.A27147 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 is considered to be suitable only for topical anesthesia. The FDA removed all parenteral butamben products from the market, possibly due to the poor solubility of this drug.A254247,L43942

Struktur Molekul 2D

Berat 193.246
Wujud solid

Peta Jejaring Molekuler
Legenda: Obat • Target • Gen • Enzim • (Panah → menunjukkan arah efek / relasi) • Transporter • Carrier

Profil Farmakokinetik

Waktu Paruh (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.[T176]
Volume Distribusi This pharmacokinetic property has not been determined.
Klirens (Clearance) Clearance is flow-limited and it highly depends on the state of protein-bound form.[A32675]

Absorpsi

When butamben is administered epidurally in a suspension form, the physical characteristics of butamben allow a very slow release.L2445 When administered topically, butamben is also reported to have a very low systemic absorption which allows for a longer duration of action.T173

Metabolisme

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.T174

Rute Eliminasi

The metabolites found in plasma after cholinesterase processing are disposed of in the urine.T174

Interaksi Obat

1055 Data
Hyaluronidase (ovine) Hyaluronidase (ovine) can cause an increase in the absorption of Butamben resulting in an increased serum concentration and potentially a worsening of adverse effects.
Hyaluronidase (human recombinant) Hyaluronidase (human recombinant) can cause an increase in the absorption of Butamben resulting in an increased serum concentration and potentially a worsening of adverse effects.
Hyaluronidase Hyaluronidase can cause an increase in the absorption of Butamben resulting in an increased serum concentration and potentially a worsening of adverse effects.
Cyclobenzaprine The risk or severity of CNS depression can be increased when Cyclobenzaprine is combined with Butamben.
Metoclopramide The risk or severity of sedation can be increased when Metoclopramide is combined with Butamben.
Lasmiditan The risk or severity of adverse effects can be increased when Lasmiditan is combined with Butamben.
Tramadol The risk or severity of CNS depression can be increased when Butamben is combined with Tramadol.
Ziprasidone The risk or severity of adverse effects can be increased when Butamben is combined with Ziprasidone.
Haloperidol The risk or severity of CNS depression can be increased when Haloperidol is combined with Butamben.
Fluoxetine Butamben may increase the central nervous system depressant (CNS depressant) activities of Fluoxetine.
Oliceridine The risk or severity of hypotension, sedation, death, somnolence, and respiratory depression can be increased when Butamben is combined with Oliceridine.
Ropeginterferon alfa-2b The risk or severity of neuropsychiatric effects can be increased when Ropeginterferon alfa-2b is combined with Butamben.
Daridorexant The risk or severity of CNS depression can be increased when Butamben is combined with Daridorexant.
Baclofen Baclofen may increase the central nervous system depressant (CNS depressant) activities of Butamben.
Lidocaine The risk or severity of methemoglobinemia can be increased when Lidocaine is combined with Butamben.
Ropivacaine The risk or severity of methemoglobinemia can be increased when Ropivacaine is combined with Butamben.
Bupivacaine The risk or severity of methemoglobinemia can be increased when Bupivacaine is combined with Butamben.
Cinchocaine The risk or severity of methemoglobinemia can be increased when Cinchocaine is combined with Butamben.
Dyclonine The risk or severity of methemoglobinemia can be increased when Dyclonine is combined with Butamben.
Procaine The risk or severity of methemoglobinemia can be increased when Procaine is combined with Butamben.
Prilocaine The risk or severity of methemoglobinemia can be increased when Prilocaine is combined with Butamben.
Proparacaine The risk or severity of methemoglobinemia can be increased when Proparacaine is combined with Butamben.
Meloxicam The risk or severity of methemoglobinemia can be increased when Meloxicam is combined with Butamben.
Oxybuprocaine The risk or severity of methemoglobinemia can be increased when Oxybuprocaine is combined with Butamben.
Cocaine The risk or severity of methemoglobinemia can be increased when Cocaine is combined with Butamben.
Mepivacaine The risk or severity of methemoglobinemia can be increased when Mepivacaine is combined with Butamben.
Levobupivacaine The risk or severity of methemoglobinemia can be increased when Levobupivacaine is combined with Butamben.
Diphenhydramine The risk or severity of methemoglobinemia can be increased when Diphenhydramine is combined with Butamben.
Benzocaine The risk or severity of methemoglobinemia can be increased when Benzocaine is combined with Butamben.
Chloroprocaine The risk or severity of methemoglobinemia can be increased when Chloroprocaine is combined with Butamben.
Phenol The risk or severity of methemoglobinemia can be increased when Phenol is combined with Butamben.
Tetrodotoxin The risk or severity of methemoglobinemia can be increased when Tetrodotoxin is combined with Butamben.
Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Benzyl alcohol is combined with Butamben.
Capsaicin The risk or severity of methemoglobinemia can be increased when Capsaicin is combined with Butamben.
Etidocaine The risk or severity of methemoglobinemia can be increased when Etidocaine is combined with Butamben.
Articaine The risk or severity of methemoglobinemia can be increased when Articaine is combined with Butamben.
Tetracaine The risk or severity of methemoglobinemia can be increased when Tetracaine is combined with Butamben.
Propoxycaine The risk or severity of methemoglobinemia can be increased when Propoxycaine is combined with Butamben.
Pramocaine The risk or severity of methemoglobinemia can be increased when Pramocaine is combined with Butamben.
Butacaine The risk or severity of methemoglobinemia can be increased when Butamben is combined with Butacaine.
Oxetacaine The risk or severity of methemoglobinemia can be increased when Butamben is combined with Oxetacaine.
Ethyl chloride The risk or severity of methemoglobinemia can be increased when Butamben is combined with Ethyl chloride.
Butanilicaine The risk or severity of methemoglobinemia can be increased when Butamben is combined with Butanilicaine.
Metabutethamine The risk or severity of methemoglobinemia can be increased when Butamben is combined with Metabutethamine.
Quinisocaine The risk or severity of methemoglobinemia can be increased when Butamben is combined with Quinisocaine.
Cetuximab The risk or severity of methemoglobinemia can be increased when Cetuximab is combined with Butamben.
Denileukin diftitox The risk or severity of methemoglobinemia can be increased when Denileukin diftitox is combined with Butamben.
Leuprolide The risk or severity of methemoglobinemia can be increased when Leuprolide is combined with Butamben.
Peginterferon alfa-2a The risk or severity of methemoglobinemia can be increased when Peginterferon alfa-2a is combined with Butamben.
Goserelin The risk or severity of methemoglobinemia can be increased when Goserelin is combined with Butamben.
Asparaginase Escherichia coli The risk or severity of methemoglobinemia can be increased when Asparaginase Escherichia coli is combined with Butamben.
Interferon alfa-2a The risk or severity of methemoglobinemia can be increased when Interferon alfa-2a is combined with Butamben.
Aldesleukin The risk or severity of methemoglobinemia can be increased when Aldesleukin is combined with Butamben.
Gemtuzumab ozogamicin The risk or severity of methemoglobinemia can be increased when Gemtuzumab ozogamicin is combined with Butamben.
Pegaspargase The risk or severity of methemoglobinemia can be increased when Pegaspargase is combined with Butamben.
Trastuzumab The risk or severity of methemoglobinemia can be increased when Trastuzumab is combined with Butamben.
Rituximab The risk or severity of methemoglobinemia can be increased when Rituximab is combined with Butamben.
Tositumomab The risk or severity of methemoglobinemia can be increased when Tositumomab is combined with Butamben.
Alemtuzumab The risk or severity of methemoglobinemia can be increased when Alemtuzumab is combined with Butamben.
Octreotide The risk or severity of methemoglobinemia can be increased when Octreotide is combined with Butamben.
Interferon alfa-2b The risk or severity of methemoglobinemia can be increased when Interferon alfa-2b is combined with Butamben.
Bevacizumab The risk or severity of methemoglobinemia can be increased when Bevacizumab is combined with Butamben.
Masoprocol The risk or severity of methemoglobinemia can be increased when Masoprocol is combined with Butamben.
Bortezomib The risk or severity of methemoglobinemia can be increased when Bortezomib is combined with Butamben.
Pipobroman The risk or severity of methemoglobinemia can be increased when Pipobroman is combined with Butamben.
Cladribine The risk or severity of methemoglobinemia can be increased when Cladribine is combined with Butamben.
Cabergoline The risk or severity of methemoglobinemia can be increased when Cabergoline is combined with Butamben.
Anagrelide The risk or severity of methemoglobinemia can be increased when Anagrelide is combined with Butamben.
Carmustine The risk or severity of methemoglobinemia can be increased when Carmustine is combined with Butamben.
Chlorotrianisene The risk or severity of methemoglobinemia can be increased when Chlorotrianisene is combined with Butamben.
Amsacrine The risk or severity of methemoglobinemia can be increased when Amsacrine is combined with Butamben.
Pamidronic acid The risk or severity of methemoglobinemia can be increased when Pamidronic acid is combined with Butamben.
Bleomycin The risk or severity of methemoglobinemia can be increased when Bleomycin is combined with Butamben.
Chlorambucil The risk or severity of methemoglobinemia can be increased when Chlorambucil is combined with Butamben.
Raltitrexed The risk or severity of methemoglobinemia can be increased when Raltitrexed is combined with Butamben.
Mitomycin The risk or severity of methemoglobinemia can be increased when Mitomycin is combined with Butamben.
Bexarotene The risk or severity of methemoglobinemia can be increased when Bexarotene is combined with Butamben.
Vindesine The risk or severity of methemoglobinemia can be increased when Vindesine is combined with Butamben.
Valproic acid The risk or severity of methemoglobinemia can be increased when Valproic acid is combined with Butamben.
Gefitinib The risk or severity of methemoglobinemia can be increased when Gefitinib is combined with Butamben.
Floxuridine The risk or severity of methemoglobinemia can be increased when Floxuridine is combined with Butamben.
Megestrol acetate The risk or severity of methemoglobinemia can be increased when Megestrol acetate is combined with Butamben.
Tioguanine The risk or severity of methemoglobinemia can be increased when Tioguanine is combined with Butamben.
Aminoglutethimide The risk or severity of methemoglobinemia can be increased when Aminoglutethimide is combined with Butamben.
Vinorelbine The risk or severity of methemoglobinemia can be increased when Vinorelbine is combined with Butamben.
Valrubicin The risk or severity of methemoglobinemia can be increased when Valrubicin is combined with Butamben.
Sorafenib The risk or severity of methemoglobinemia can be increased when Sorafenib is combined with Butamben.
Streptozocin The risk or severity of methemoglobinemia can be increased when Streptozocin is combined with Butamben.
Trifluridine The risk or severity of methemoglobinemia can be increased when Trifluridine is combined with Butamben.
Gemcitabine The risk or severity of methemoglobinemia can be increased when Gemcitabine is combined with Butamben.
Teniposide The risk or severity of methemoglobinemia can be increased when Teniposide is combined with Butamben.
Epirubicin The risk or severity of methemoglobinemia can be increased when Epirubicin is combined with Butamben.
Lenalidomide The risk or severity of methemoglobinemia can be increased when Lenalidomide is combined with Butamben.
Altretamine The risk or severity of methemoglobinemia can be increased when Altretamine is combined with Butamben.
Flutamide The risk or severity of methemoglobinemia can be increased when Flutamide is combined with Butamben.
Cisplatin The risk or severity of methemoglobinemia can be increased when Cisplatin is combined with Butamben.
Alitretinoin The risk or severity of methemoglobinemia can be increased when Alitretinoin is combined with Butamben.
Oxaliplatin The risk or severity of methemoglobinemia can be increased when Oxaliplatin is combined with Butamben.
Erlotinib The risk or severity of methemoglobinemia can be increased when Erlotinib is combined with Butamben.
Cyclophosphamide The risk or severity of methemoglobinemia can be increased when Cyclophosphamide is combined with Butamben.

Target Protein

Voltage-dependent calcium channel CACNG1
ATP-sensitive potassium channel KCNJ1
Transient receptor potential cation channel subfamily A member 1 TRPA1
Transient receptor potential cation channel subfamily V member 4 TRPV4

Referensi & Sumber

Artikel (PubMed)
  • PMID: 16368819
    Beekwilder JP, van Kempen GT, van den Berg RJ, Ypey DL: The local anesthetic butamben inhibits and accelerates low-voltage activated T-type currents in small sensory neurons. Anesth Analg. 2006 Jan;102(1):141-5.
  • PMID: 15920194
    Beekwilder JP, Winkelman DL, van Kempen GT, van den Berg RJ, Ypey DL: The block of total and N-type calcium conductance in mouse sensory neurons by the local anesthetic n-butyl-p-aminobenzoate. Anesth Analg. 2005 Jun;100(6):1674-9. doi: 10.1213/01.ANE.0000151162.07211.DD.
  • PMID: 15923341
    Winkelman DL, Beck CL, Ypey DL, O'Leary ME: Inhibition of the A-type K+ channels of dorsal root ganglion neurons by the long-duration anesthetic butamben. J Pharmacol Exp Ther. 2005 Sep;314(3):1177-86. doi: 10.1124/jpet.105.087759. Epub 2005 May 27.
  • PMID: 22190922
    Shipton EA: New formulations of local anaesthetics-part I. Anesthesiol Res Pract. 2012;2012:546409. doi: 10.1155/2012/546409. Epub 2011 Dec 5.
  • PMID: 34204807
    Mura P, Maestrelli F, Cirri M, Nerli G, Di Cesare Mannelli L, Ghelardini C, Mennini N: Improvement of Butamben Anesthetic Efficacy by the Development of Deformable Liposomes Bearing the Drug as Cyclodextrin Complex. Pharmaceutics. 2021 Jun 12;13(6). pii: pharmaceutics13060872. doi: 10.3390/pharmaceutics13060872.
Textbook
  • ISBN: 1-58255-320-3
    Schilling J. (2004). Pharmacology. A2-in-1 reference for nurses. Lippincott Williams & Wilkins.
  • Buch J. (2010). Clinically oriented pharmacology (2nd ed.). PDU Medical College.
  • ISBN: 978-0323-07371-4
    Daskalos D. (2012). Local anesthesia for the dental hygienist. Elsevier.
  • Rossoff I. (1974). Handbook of veterinary drugs. Springer.
  • ISBN: 3-7186-5247-1
    Whateley T. (1992). Microencapsulation of drugs. Hardwood Academic Publishers..

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