(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide

• ChemBase ID: 181
• Molecular Formular: C17H26N2O
• Molecular Mass: 274.40114
• Monoisotopic Mass: 274.20451346
• SMILES: O=C(Nc1c(cccc1C)C)[C@H]1N(CCCC1)CCC
• Canonical SMILES: CCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
• InChI: InChI=1S/C17H26N2O/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20)/t15-/m0/s1
• InChIKey: ZKMNUMMKYBVTFN-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
• IUPAC Traditional name: @ropivacaine
• Brand Name: Naropin
• Synonyms: Ropivacaina [INN-Spanish]; Ropivacainum [INN-Latin]; Ropivacaine [INN]; Ropivacaina [Spanish]; S-Ropivacaine; Ropivacaine

Database IDs

• CAS Number: 84057-95-4
• PubChem SID: 160963644
• PubChem CID: 175805

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.623526
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.7783761
• LogD (pH = 7.4): 3.5127594
• Log P: 4.07095
• Molar Refractivity: 85.5923 cm^3
• Polarizability: 32.441116 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.91
• LOG S: -3.04
• Solubility (Water): 2.53e-01 g/l

PROPERTIES

Physical Property

• Solubility: 57.6 mg/L
• Hydrophobicity(logP): 3

DETAILS

DrugBank - DB00296

• Drug Groups: approved
• Description: Ropivacaine is a local anaesthetic drug belonging to the amino amide group. The name ropivacaine refers to both the racemate and the marketed S-enantiomer. Ropivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Naropin. [Wikipedia]
• Indication: Used in obstetric anesthesia and regional anesthesia for surgery.
• Pharmacology: Ropivacaine, a local anesthetic agent, is indicated for the production of local or regional anesthesia or analgesia for surgery, for oral surgery procedures, for diagnostic and therapeutic procedures, and for obstetrical procedures.
• Toxicity: Systemic exposure to excessive quantities of ropivacaine mainly result in central nervous system (CNS) and cardiovascular effects – CNS effects usually occur at lower blood plasma concentrations and additional cardiovascular effects present at higher concentrations, though cardiovascular collapse may also occur with low concentrations. CNS effects may include CNS excitation (nervousness, tingling around the mouth, tinnitus, tremor, dizziness, blurred vision, seizures) followed by depression (drowsiness, loss of consciousness, respiratory depression and apnea). Cardiovascular effects include hypotension, bradycardia, arrhythmias, and/or cardiac arrest – some of which may be due to hypoxemia secondary to respiratory depression.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Bioavailability is 87%–98% following epidural administration.
• Half Life: Approximately 4.2 hours.
• Protein Binding: 94%, mainly to a1-acid glycoprotein
• Elimination: Ropivacaine is extensively metabolized in the liver, predominantly by aromatic hydroxylation mediated by cytochrome P4501A to 3-hydroxy ropivacaine. After a single IV dose approximately 37% of the total dose is excreted in the urine as both free and conjugated 3-hydroxy ropivacaine. In total, 86% of the ropivacaine dose is excreted in the urine after intravenous administration of which only 1% relates to unchanged drug.
• Clearance: * 387?+/- 107 mL/min; * unbound plasma clearance=7.2 +/- 1.6 L/min
• References: Weinberg G, Ripper R, Feinstein DL, Hoffman W: Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity. Reg Anesth Pain Med. 2003 May-Jun;28(3):198-202. [Pubmed] ; Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. [Pubmed] ; Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Weinberg G, Ripper R, Feinstein DL, Hoffman W: Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity. Reg Anesth Pain Med. 2003 May-Jun;28(3):198-202. Pubmed
• Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. Pubmed
• Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8. Pubmed