Structure via PubChem · Public domain (PubChem)
benzocaine
Sign in to saveAlso known as Baby Anbesol, Americaine, Ethyl p-Aminophenylcarboxylate, p-(Ethoxycarbonyl)aniline, p-Ethoxycarboxylic Aniline, Benzocainum, Amben ethyl ester, p-Carbethoxyaniline
Benzocaine, sold under the brand name Orajel amongst others, is a local anesthetic, belonging to the amino ester drug class, commonly used as a topical painkiller or in cough drops. It is the active ingredient in many over-the-counter anesthetic ointments such as products for oral ulcers. It is combined with antipyrine to form A/B ear drops. In the US, products containing benzocaine for oral application are contraindicated in children younger than two years old.
Key facts
- Drug.image
- Benzocaine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.image2
- Benzocaine-from-xtal-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200
- Drug.tradename
- Anbesol, Lanacane, Orajel, others
- Drug.routes_of_administration
- Topical, Oral
- Drug.ATC_prefix
- C05
- Drug.ATC_suffix
- AD03
- Drug.ATC_supplemental
- , , ,
- Drug.legal_AU
- S4
- Drug.legal_AU_comment
- /Schedule 2
- Drug.legal_UK
- GSL, P
- Drug.legal_US
- OTC
- Drug.CAS_number
- 94-09-7
- Drug.PubChem
- 2337
- Drug.DrugBank
- DB01086
via Wikipedia infobox
Chemical data
- Formula
- C9H11NO2
- Molecular weight
- 165.19 g/mol
- IUPAC name
- ethyl 4-aminobenzoate
- SMILES
- CCOC(=O)C1=CC=C(C=C1)N
- InChIKey
- BLFLLBZGZJTVJG-UHFFFAOYSA-N
- XLogP
- 1.9
- Polar surface area
- 52.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
1,692 papers- Benzocaine: Review on a Drug with Unfold Potential.Mini reviews in medicinal chemistry · 2020
- Benzocaine-Associated Methemoglobinemia.American journal of therapeutics · 2018
- Benzocaine-Induced Methemoglobinemia.The Journal of emergency medicine · 2017
- Benzocaine-induced methemoglobinemia in the pediatric population.Journal of pediatric nursing · 2012
- Benzocaine-induced methemoglobinemia.American journal of diseases of children (1960) · 1977
via PubMed
~5 min read
Encyclopedic overview
10 sectionsContents
- Medical uses
- Other uses
- Available forms
- Side effects
- Chemistry
- Synthesis
- History
- Society and culture
- Veterinary uses
- References
Benzocaine, sold under the brand name Orajel amongst others, is a local anesthetic, belonging to the amino ester drug class, commonly used as a topical painkiller or in cough drops. It is the active ingredient in many over-the-counter anesthetic ointments such as products for oral ulcers. It is combined with antipyrine to form A/B ear drops. In the US, products containing benzocaine for oral application are contraindicated in children younger than two years old.
It was first synthesised in 1890 in Germany and approved for medical use in 1902.
Excerpted from Wikipedia’s “benzocaine” article, available under the CC BY-SA 4.0 licence.