Benzocaine
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Basic Info
| Common Name | Benzocaine(F04781) |
| 2D Structure | |
| Description | Benzocaine is a surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings. Benzocaine is a local anesthetic commonly used as a topical pain reliever. It is the active ingredient in many over-the-counter analgesic ointments. Benzocaine is an ester, a compound made from the organic acid PABA (para-aminobenzoic acid) and ethanol. The process in which this ester is created is known as Fischer esterification. |
| FRCD ID | F04781 |
| CAS Number | 94-09-7 |
| PubChem CID | 2337 |
| Formula | C9H11NO2 |
| IUPAC Name | ethyl 4-aminobenzoate |
| InChI Key | BLFLLBZGZJTVJG-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3 |
| Canonical SMILES | CCOC(=O)C1=CC=C(C=C1)N |
| Isomeric SMILES | CCOC(=O)C1=CC=C(C=C1)N |
| Wikipedia | Benzocaine |
| Synonyms |
Ethyl p-aminobenzoate
benzocaine
Ethyl 4-aminobenzoate
94-09-7
Ethyl aminobenzoate
Americaine
Anesthesin
Anaesthesin
Ethoform
Norcaine
|
| Classifies |
Predicted: Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzoic acid esters |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Aminobenzoic acid or derivatives - Benzoate ester - Benzoyl - Aniline or substituted anilines - Amino acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Amine - Organonitrogen compound - Organooxygen compound - Primary amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 165.192 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 151 |
| Monoisotopic Mass | 165.079 |
| Exact Mass | 165.079 |
| XLogP | 1.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9609 |
| Human Intestinal Absorption | HIA+ | 0.9963 |
| Caco-2 Permeability | Caco2+ | 0.7814 |
| P-glycoprotein Substrate | Non-substrate | 0.8329 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9589 |
| Non-inhibitor | 0.9612 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8818 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5128 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8426 |
| CYP450 2D6 Substrate | Non-substrate | 0.7934 |
| CYP450 3A4 Substrate | Non-substrate | 0.7513 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9107 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9370 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7883 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9721 |
| Non-inhibitor | 0.9668 | |
| AMES Toxicity | Non AMES toxic | 0.8825 |
| Carcinogens | Carcinogens | 0.5130 |
| Fish Toxicity | High FHMT | 0.7229 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9508 |
| Honey Bee Toxicity | Low HBT | 0.5842 |
| Biodegradation | Ready biodegradable | 0.7718 |
| Acute Oral Toxicity | III | 0.7993 |
| Carcinogenicity (Three-class) | Non-required | 0.5528 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.4862 | LogS |
| Caco-2 Permeability | 1.4667 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7665 | LD50, mol/kg |
| Fish Toxicity | 1.7727 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2941 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Shelled Molluscas | Japan | 0.05ppm | |||
| Other Fish | Japan | 0.05ppm | |||
| Perciformes | Japan | 0.05ppm | |||
| Anguilliformes | Japan | 0.05ppm | |||
| Salmoniformes | Japan | 0.05ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Organized polysaccharide fibers as stable drug carriers. | Carbohydr Polym | 2013 Apr 15 | 23544530 |
| The in vitro and in vivo genotoxicity of benzocaine: a brief communication. | Int J Toxicol | 2012 Jun | 22556388 |
| Crop grouping: a proposal for public aquaculture. | Vet Hum Toxicol | 1998 | 9823579 |
| Potential for an external vaginal antiitch cream containing benzocaine to cause methemoglobinemia in healthy women. | Am J Obstet Gynecol | 1997 May | 9166159 |
| Effects of carbohydrate intake on subsequent food intake and mood state. | Physiol Behav | 1995 Sep | 8587947 |
| Effects of contact sensitizers neomycin sulfate, benzocaine and 2,4-dinitrobenzene 1-sulfonate, sodium salt on viability, membrane integrity and IL-1 alpha mRNA expression of cultured normal human keratinocytes. | Food Chem Toxicol | 1995 Jan | 7821878 |
| In vitro skin absorption and metabolism of benzoic acid, p-aminobenzoic acid, andbenzocaine in the hairless guinea pig. | Pharm Res | 1990 Nov | 2293213 |
| ANAPHYLACTIC REACTIONS FROM SHELLFISH. | Dermatol Trop Ecol Geogr | 1964 Apr-Jun | 14201332 |
Targets
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. Plays a role in neuropathic pain mechanisms.
- Gene Name:
- SCN10A
- Uniprot ID:
- Q9Y5Y9
- Molecular Weight:
- 220623.605 Da
- Mechanism of Action:
- Benzocaine binds to sodium channel and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions. Depolarization of the neuronal membrane is inhibited thereby blocking the initiation and conduction of nerve impulses.
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
- Gene Name:
- NR1H4
- Uniprot ID:
- Q96RI1
- Molecular Weight:
- 55913.915 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXRs is 9-cis retinoic acid. RXRA serves as a common heterodimeric partner for a number of nuclear receptors. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. The RXRA/PPARA heterodimer is required for PPARA transcriptional activity on fatty acid oxidation genes such as ACOX1 and the P450 system genes.
- Gene Name:
- RXRA
- Uniprot ID:
- P19793
- Molecular Weight:
- 50810.835 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]