Benzocaine
Editor-In-Chief: C. Michael Gibson, M.S., M.D. [2]
Overview
| |
| Benzocaine
| |
| Systematic (IUPAC) name | |
| ethyl 4-aminobenzoate | |
| Identifiers | |
| CAS number | |
| ATC code | C05 D04AB04, N01BA05, R02AD01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C9H11NO2 |
| Mol. mass | 165.189 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
C (USA) |
| Legal status |
|
| Routes | topical |
|
WikiDoc Resources for Benzocaine | |
|
Articles | |
|---|---|
|
Most recent articles on Benzocaine | |
|
Media | |
|
Evidence Based Medicine | |
|
Clinical Trials | |
|
Ongoing Trials on Benzocaine at Clinical Trials.gov Clinical Trials on Benzocaine at Google
| |
|
Guidelines / Policies / Govt | |
|
US National Guidelines Clearinghouse on Benzocaine
| |
|
Books | |
|
News | |
|
Commentary | |
|
Definitions | |
|
Patient Resources / Community | |
|
Patient resources on Benzocaine Discussion groups on Benzocaine Patient Handouts on Benzocaine Directions to Hospitals Treating Benzocaine Risk calculators and risk factors for Benzocaine
| |
|
Healthcare Provider Resources | |
|
Causes & Risk Factors for Benzocaine | |
|
Continuing Medical Education (CME) | |
|
International | |
|
| |
|
Business | |
|
Experimental / Informatics | |
Benzocaine is a local anesthetic commonly used as a topical pain reliever. It is the active ingredient in many over-the-counter anesthetic ointments, including oral pain relievers such as Orajel and topical pain relievers such as Lanacane.
Chemical properties
Benzocaine is an ester, and can be prepared from the organic acid PABA (para-aminobenzoic acid) and ethanol by Fischer esterification. The melting point of Benzocaine is 88-90 degrees Celsius, and the boiling point is 172 degrees Celsius. The density of Benzocaine is 1.17g/cm3
History
Benzocaine was first synthesised by a German chemical firm named Ritsert, in the town of Eberbach, in Baden-Württemberg in 1902.
How it relieves pain
Pain is caused by the stimulation of free nerve endings. When the nerve endings are stimulated, sodium enters the neuron, which causes an electrical potential to build up in the nerve. Once the electrical potential becomes big enough the signal is propagated down the nerve toward the central nervous system, which interprets this as pain.
Esters of PABA work as a chemical barrier, stopping the sodium from being able to enter the nerve ending.
Side effects
Allergic reactions occur with ester local anaesthetics (like benzocaine) because of the PABA structure.
Benzocaine also is a well-known cause of methemoglobinemia. Because it may be used in topical creams with a concentration as much as 20%, it is not difficult to administer a dose sufficient to cause this problem.
Other uses
Benzocaine can also be used as a fish tranquilizer. Due to its low solubility in water, stock solution can be made with ethanol (95%). 25 g of benzocaine per 200 ml ethanol will make a solution strong enough to knock saltwater fish out in 2-4 minutes. They will regain equilibrium after 10-15 minutes. Use 5 ml stock solution per 1 L of saltwater. Some benzocaine will precipitate out of solution when added to the saltwater, so it is recommended to add the volume of stock solution you will be using to a separate container and mix it with some saltwater before adding it to the tank.
Benzocaine is also used as a key ingredient in Phenazone, an anti-inflammatory, and is also used in some glycerol-based ear medications for use in removing excess wax as well as ear conditions such as Otitis Media and swimmers ear.
It is also used in certain condoms to prolong sex by numbing the penis.[1]
Benzocaine is an ingredient in some anal sex lubricants.[2]
References
External links
- FDA investigation of the possible adverse effects of benzocaine mouth and throat sprays.
- http://www.endonurse.com
Vasoprotectives (C05) | |
|---|---|
| Antihemorrhoidals for topical use | corticosteroids (Hydrocortisone, Prednisolone, Betamethasone, Fluorometholone, Fluocortolone, Dexamethasone, Fluocinolone acetonide, Fluocinonide) - local anesthetics (Lidocaine, Tetracaine, Benzocaine, Cinchocaine, Procaine, Oxetacaine, Pramocaine) - other (Tribenoside) |
| Antivaricose therapy | heparins or heparinoids for topical use (Organo-heparinoid, Sodium apolate, Heparin, Pentosan polysulfate) - sclerosing agents for local injection (Monoethanolamine oleate, Polidocanol, Invert sugar, Sodium tetradecyl sulfate, Phenol) - Other (Calcium dobesilate) |
| Capillary stabilising agents | bioflavonoids (Rutoside, Monoxerutin, Diosmin, Troxerutin, Hidrosmin) - other (Tribenoside) |
Antipruritics (D04) | |
|---|---|
| Antihistamines for topical use | Thonzylamine - Mepyramine - Thenalidine - Tripelennamine - Chloropyramine - Promethazine - Tolpropamine - Dimetindene - Clemastine - Bamipine - Isothipendyl - Diphenhydramine - Chlorphenoxamine |
| Anesthetics for topical use | Lidocaine - Cinchocaine - Oxybuprocaine - Benzocaine - Quinisocaine - Tetracaine - Pramocaine |
Throat preparations (R02) | |
|---|---|
| Antiseptics | Ambazone - Dequalinium - Dichlorobenzyl alcohol - Chlorhexidine - Cetylpyridinium - Benzethonium - Myristyl-benzalkonium - Chlorquinaldol - Hexylresorcinol - Acriflavinium chloride - Oxyquinoline - Povidone-iodine - Benzalkonium - Cetrimonium - Hexamidine - Phenol |
| Antibiotics | Neomycin - Tyrothricin - Fusafungine - Bacitracin - Gramicidin |
| Local anesthetics | Benzocaine - Lidocaine - Cocaine - Dyclonine |
de:Benzocainit:Benzocaina
he:בנזוקאין
hu:Benzokain
nl:Benzocaïne
Table of Contents In Alphabetical Order | By Individual Diseases | Signs and Symptoms | Physical Examination | Lab Tests | Drugs
Editor Tools Become an Editor | Editors Help Menu | Create a Page | Edit a Page | Upload a Picture or File | Printable version | Permanent link | Maintain Pages | What Pages Link HereThere is no pharmaceutical or device industry support for this site and we need your viewer supported Donations | Editorial Board | Governance | Licensing | Disclaimers | Avoid Plagiarism | Policies
