2-(diethylamino)ethyl 4-amino-2-chlorobenzoate

• ChemBase ID: 1032
• Molecular Formular: C13H19ClN2O2
• Molecular Mass: 270.75516
• Monoisotopic Mass: 270.11350554
• SMILES: Clc1c(C(=O)OCCN(CC)CC)ccc(N)c1
• Canonical SMILES: CCN(CCOC(=O)c1ccc(cc1Cl)N)CC
• InChI: InChI=1S/C13H19ClN2O2/c1-3-16(4-2)7-8-18-13(17)11-6-5-10(15)9-12(11)14/h5-6,9H,3-4,7-8,15H2,1-2H3
• InChIKey: VDANGULDQQJODZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(diethylamino)ethyl 4-amino-2-chlorobenzoate
• IUPAC Traditional name: chloroprocaine
• Brand Name: Nesacaine-MPF; Nesacaine-CE; Halestyn
• Synonyms: Chloroprocaine hydrochloride; Chloroprocain; Chlorprocaine; Chloroprocaine

Database IDs

• CAS Number: 133-16-4
• PubChem SID: 46508245; 160964495
• PubChem CID: 8612
• CHEBI ID: 3636
• ATC CODE: N01BA04
• CHEMBL: 1179047
• Chemspider ID: 8293
• DrugBank ID: DB01161
• KEGG ID: D07678
• Unique Ingredient Identifier: 5YVB0POT2H
• Wikipedia Title: Chloroprocaine

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.69620055
• LogD (pH = 7.4): 0.91574985
• Log P: 2.484102
• Molar Refractivity: 75.1048 cm^3
• Polarizability: 28.5181 Å^3
• Polar Surface Area: 55.56 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.72
• LOG S: -2.32
• Solubility (Water): 1.30e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.665 mg/mL
• Hydrophobicity(logP): 2.5

DETAILS

DrugBank - DB01161

• Drug Groups: approved
• Description: Chloroprocaine hydrochloride is a local anesthetic given by injection during surgical procedures and labor and delivery. Chloroprocaine, like other local anesthetics, blocks the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse and by reducing the rate of rise of the action potential.
• Indication: For the production of local anesthesia by infiltration and peripheral nerve block. They are not to be used for lumbar or caudal epidural anesthesia.
• Pharmacology: Chloroprocaine is an anesthetic agent indicated for production of local or regional anesthesia, particularly for oral surgery. Chloroprocaine (like cocaine) has the advantage of constricting blood vessels which reduces bleeding, unlike other local anesthetics like lidocaine. Chloroprocaine is an ester anesthetic.
• Toxicity: In mice, the intravenous LD₅₀ of chloroprocaine HCl is 97 mg/kg and the subcutaneous LD₅₀ of chloroprocaine HCl is 950 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: Chloroprocaine is rapidly metabolized in plasma by hydrolysis of the ester linkage by pseudocholinesterase.
• Absorption: The rate of systemic absorption of local anesthetic drugs is dependent upon the total dose and concentration of drug administered, the route of administration, the vascularity of the administration site, and the presence or absence of epinephrine in the anesthetic injection.
• Half Life: 21 +/- 2 seconds
• Elimination: Chloroprocaine is rapidly metabolized in plasma by hydrolysis of the ester linkage by pseudocholinesterase. Urinary excretion is affected by urinary perfusion and factors affecting urinary pH.
• External Links: Wikipedia; RxList