2-(diethylamino)ethyl 3-amino-4-propoxybenzoate

• ChemBase ID: 686
• Molecular Formular: C16H26N2O3
• Molecular Mass: 294.38924
• Monoisotopic Mass: 294.1943427
• SMILES: O(CCN(CC)CC)C(=O)c1cc(N)c(OCCC)cc1
• Canonical SMILES: CCCOc1ccc(cc1N)C(=O)OCCN(CC)CC
• InChI: InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3
• InChIKey: KCLANYCVBBTKTO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
• IUPAC Traditional name: proparacaine
• Brand Name: Ophthaine; Ophthetic; Paracaine; Spectro-Caine; Ak-Taine; Alcaine; Diocaine; Kainair; Ocu-Caine
• Synonyms: Proximetacaina [INN-Spanish]; Prossimetacaina [Dcit]; Proparacaine Hcl; Proximetacainum; Proxymetacaine; Proxymetacaine Hcl; Proxymetacainum [INN-Latin]; Proparacaine; Proxymetacaine

Database IDs

• CAS Number: 499-67-2
• PubChem SID: 46507960; 160964149
• PubChem CID: 4935
• ATC CODE: S01HA04
• CHEMBL: 1196
• Chemspider ID: 4766
• DrugBank ID: DB00807
• KEGG ID: D08448
• Unique Ingredient Identifier: B4OB0JHI1X
• Wikipedia Title: Proxymetacaine

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.579591
• LogD (pH = 7.4): 1.0333513
• Log P: 2.6017163
• Molar Refractivity: 86.0358 cm^3
• Polarizability: 32.82243 Å^3
• Polar Surface Area: 64.79 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.97
• LOG S: -2.33
• Solubility (Water): 1.39e+00 g/l

PROPERTIES

Physical Property

• Solubility: Soluble
• Hydrophobicity(logP): 2.5

Pharmacology Properties

• Admin Routes: Topical (eye drops)
• Metabolism: Plasma
• Pregnancy Category: C (US)

DETAILS

DrugBank - DB00807

• Drug Groups: approved
• Description: Proparacaine is a topical anesthetic drug of the amino ester group. It is available as its hydrochloride salt in ophthalmic solutions at a concentration of 0.5%. [Wikipedia]
• Indication: Used as a local (ophthalmic) anesthetic.
• Pharmacology: Proparacaine stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses thereby effecting local anesthetic action. More specifically, proparacaine appears to bind or antagonize the function of voltage gated sodium channels.
• Affected Organisms: Humans and other mammals
• Biotransformation: Plasma
• External Links: Wikipedia; RxList; Drugs.com