Basic information
- CAS
99-43-4- Standard SMILES
CCCCOc1cc(C(=O)OCCN(CC)CC)ccc1N- InChIKey
CMHHMUWAYWTMGS-UHFFFAOYSA-N- Molecular formula
- C17H28N2O3
- Average molar mass
- 308.4 g/mol
- Monoisotopic mass
- 308.20999276
Overview
Oxybuprocaine is a benzoate ester in which 4-amino-3-butoxybenzoic acid and 2-(diethylamino)ethanol have combined to form the ester bond; an ester-based local anaesthetic (ester "caine") used especially in ophthalmology and otolaryngology. It has a role as a local anaesthetic, a topical anaesthetic and a drug allergen. It is a benzoate ester, an amino-acid ester, a substituted aniline and a tertiary amino compound. It is functionally related to a 2-diethylaminoethanol.
Names & identifiers
- Preferred name
- Oxybuprocaine
- IUPAC
- 2-(diethylamino)ethyl 4-amino-3-butoxybenzoate
- English name
- Oxybuprocaine
- Molecular formula
- C17H28N2O3
- Molecular weight
- 308.42
Names & synonyms
OxybuprocaineBenoxinate99-43-4Oxybucaine2-(Diethylamino)ethyl 4-amino-3-butoxybenzoateOxibuprokainOxyriprocaineConjucainDorsacainOxibuprocainaOxybuprocainumButoxyaminobenzoyldiethylaminoethanol
Show more names
BNXS-749FluressNovescineButoxyprocaineOxybuprocaine USP/EP/BP2-Diethylaminoethyl 4-amino-3-butoxybenzoate2-(Diethylamino)ethyl 4-amino-3-N-butoxybenzoate
Monofree oxybuprocaineBENZOIC ACID, 4-AMINO-3-BUTOXY-, 2-(DIETHYLAMINO)ETHYL ESTER4-Amino-3-butoxy-2-(diethylamino)ethyl ester benzoic acid4-Amino-3-n-butoxy-benzoesaeure-diaethylaminoaethylesterCHEBI:309594AXQ0JYM3034-Amino-3-butoxy-benzoic acid 2-diethylamino-ethyl esterDTXSID7048530
Database identifiers
- CAS
99-43-4- PubChem CID
- 4633
- DTXSID
DTXSID7048530- ChEMBL
CHEMBL1200
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 64.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 11
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 308
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
LogP3.1
Solubility
Very soluble (hydrochloride salt)
5.44e-01 g/L
42.7 [ug/mL] (The mean of the results at pH 7.4)
Human DrugsPharmaceuticals
Melting Point216.5 °C
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 2 · bp2 215-218°
- Density
- 1.052 · 1.052±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Methanol (Slightly)
- pka
- 9.16 · 9.16±0.25(Predicted)
- form
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
S01HA02
S - Sensory organs
D - Dermatologicals
QS - Sensory organs
QD - Dermatologicals
PharmacodynamicsOxybuprocaine is a local anaesthetic. It may be less irritating than tetracaine, and the onset and duration of action are similar to tetracaine.
Mechanism of Action
Oxybuprocaine 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.
MeSH Pharmacological Classification
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.
Cellular LocationsCytoplasm
Metabolite PathwaysOxybuprocaine Action Pathway
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >10
Use ClassificationPharmaceuticals
Applications
UsesAnesthetic (topical).
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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