Ropivacaine

Base Information Edit

Chemical Name:Ropivacaine
CAS No.:84057-95-4
Molecular Formula:C17H26N2O
Molecular Weight:274.406
Hs Code.:2933399090
European Community (EC) Number:617-525-1,691-259-4,691-561-6
UNII:7IO5LYA57N
DSSTox Substance ID:DTXSID4040187
Nikkaji Number:J33.095G
Wikipedia:Ropivacaine
Wikidata:Q279504
NCI Thesaurus Code:C61932
RXCUI:35780
Pharos Ligand ID:D4LXA9D256G2
Metabolomics Workbench ID:42685
ChEMBL ID:CHEMBL1077896
Mol file:84057-95-4.mol

Synonyms:2-Piperidinecarboxamide,N-(2,6-dimethylphenyl)-1-propyl-, (S)-;(-)-LEA 103;(-)-Ropivacaine;(S)-(-)-Ropivacaine;LEA 103;Narop;Naropeine;Naropine;Ropivacaine;S-Ropivacaine;N-(2,6-dimethylphenyl)-1-propyl-piperidine-2-carboxamide;

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Chemical Property of Ropivacaine Edit

Chemical Property:

Melting Point:144 - 146oC
Boiling Point:410.2 °C at 760 mmHg
PKA:8.16(at 25℃)
Flash Point:201.9 °C
PSA：32.34000
Density:1.044 g/cm³
LogP:3.51730
Storage Temp.:Refrigerator
Solubility.:Aqueous Acid (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Sligh
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:274.204513457
Heavy Atom Count:20
Complexity:308

Purity/Quality:

Safty Information:

Pictogram(s): Xi
Hazard Codes:Xi

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C
Isomeric SMILES:CCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C
Recent ClinicalTrials:Optimal Effective Local Anesthetic Volume for Pain Relief Using Brachial Plexus Block
Recent EU Clinical Trials:Influence of the PECS II block on postoperative pain and opioid demand in patients undergoing minimal invasive cardiac surgery
Recent NIPH Clinical Trials:A Study on the Efficacy of Opioid-Free Anesthesia in Pediatric Cardiac Surgery
Description Ropivacaine is an aminoamide local anaesthetic drug commonly marketed by AstraZeneca under the trade name Naropin. Naropin was launched in 1996 in Australia, Denmark, Finland, the Netherlands and Sweden as a local anesthetic. It can be prepared in a number of ways the most efficient involves a three step sequence beginning with L-pipecolic acid. This compound is the first one in this family to be produced as the pure (S)- enantiomer. The (R)-enantiomer has been shown to have cardiotoxic effects. Thus ropivicaine has less cardiovascular and CNS toxicity than bupivacaine. It is a Na channel blocker that is specific for affecting nerve fibers responsible for transmission of pain (Aδ and C) with no effect on fibers responsible for motor function (Aβ). Clinically, it has distinct advantages over bupivacaine. Its effects are slower in onset, less intense and have a shorter duration. This is a result of extensive metabolism in the liver to the 3-hydroxy isomer by CYPIA2 isoenzyme.Ropivacaine is an anesthetic (numbing medicine) that blocks the nerve impulses that send pain signals to your brain.Ropivacaine is used as a local (in only one area) anesthesia for a spinal block, also called an epidural. The medication is used to provide anesthesia during a surgery or C-section, or to ease labor pains.https://www.drugs.com/mtm/ropivacaine.html
Uses Ropivacaine is a pure S(-)-enantiomer of propivacaine. It is a long-acting amide local anesthetic that has efficacy and potency nearly as high as bupivacaine and levobupivacaine but has lower CNS and cvS toxicity. If there are any differences between bupivacaine and ropivacaine it is the slightly shorter period of activity in spinal and epidural applications and a lowered ability to penetrate large motor nerves. It is the reduced lipophilicity that contributed to the lowered penetration of the motor nerves, combined with its stereoselective properties that allows ropivacaine to have significantly reduced Cvs toxicity compared to bupivacaine (Simpson et al. 2005). Ropivacaine has a diphasic effect on peripheral vasculature-it is vasoconstrictive when injected at a concentration below 0.5 w/v% and there is dilation at concentrations over 1 w/v% (Cederholm et al. 1992).Ropivacaine HCl is an anaesthetic agent and blocks impulse conduction in nerve fibres through inhibiting sodium ion influx reversibly.http://www.selleckchem.com/products/ropivacaine-hcl.html (S)-Ropivacaine acts as a local anaesthetic for use during medical procedures. Frequently used in epidural procedures as a labor analgesia
Biological Functions Ropivacaine (Naropin) is a recently developed longacting amide-linked local anesthetic. Its duration of action is similar to that of bupivacaine, but it is slightly less potent and requires higher concentrations to achieve the same degree of block. Its primary advantage over bupivacaine is its lesser degree of cardiotoxicity.
Clinical Use Ropivacaine is a long-acting amide-type local anestheticwith inherent vasoconstrictor activities, so it does not requirethe use of additional vasoconstrictors. It is approved forepidural, nerve block, infiltration, and intrathecal anesthesia.

Technology Process of Ropivacaine

There total 13 articles about Ropivacaine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%