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Ropivacaine

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Ropivacaine Basic information

Product Name:
Ropivacaine
Synonyms:
  • ROPIVACAINE MESYLATER
  • RopivacaineHcl/MesylateBase
  • ROPACARAINEHCL
  • (S)-N-(2,6-Dimethylphenyl)-1-pKIpyl-2-piperidinecarboxamide
  • Naropin
  • 2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-propyl-, (2S)-
  • Naropine
  • (2S)-1-Propyl-2-(2,6-dimethylphenyl)carbamoylpiperidine
CAS:
84057-95-4
MF:
C17H26N2O
MW:
274.4
Product Categories:
  • API
Mol File:
84057-95-4.mol
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Ropivacaine Chemical Properties

Melting point:
144-146°
alpha 
D25 -82.0° (c = 2 in methanol)
Boiling point:
410.2±45.0 °C(Predicted)
Density 
1.044±0.06 g/cm3(Predicted)
pka
8.16(at 25℃)
InChIKey
ZKMNUMMKYBVTFN-HNNXBMFYSA-N
CAS DataBase Reference
84057-95-4(CAS DataBase Reference)
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Safety Information

HS Code 
2933399090

MSDS

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Ropivacaine Usage And Synthesis

Description

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.

Originator

Astra (Sweden)

Uses

Ropivacaine HCl is an anaesthetic agent and blocks impulse conduction in nerve fibres through inhibiting sodium ion influx reversibly. - See more at: http://www.selleckchem.com/products/ropivacaine-hcl.html#sthash.hTK3J8yF.dpuf

Definition

ChEBI: A piperidinecarboxamide-based amide-type local anaesthetic (amide caine) in which (S)-N-propylpipecolic acid and 2,6-dimethylaniline are combined to form the amide bond.

brand name

Narapin [as hydrochloride] (Astra).

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.

General Description

The recognized increase in cardiotoxicity of one bupivacaineisomer led to the stereospecific production of ropivacaine asthe single “S” (-) enantiomer. Ropivacaine is the propylanalog of mepivacaine (methyl) and bupivacaine (butyl). ThepKa of the tertiary nitrogen is 8.1, and it displays the same degreeof protein binding as bupivacaine ( 94%). Althoughropivacaine has similar properties as bupivacaine, it displaysless cardiotoxicity. The shortened alkyl chain gives it approximatelyone third of the lipid solubility of bupivacaine.

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.

Metabolism

The metabolism of ropivacaine in human is mediated by hepatic CYP1A2 isozymes and, to a minor extent, by CYP3A4. The major metabolite is 3-hydroxyropivacaine, and the minor metabolite is (S)-2′,6′-pipecoloxylidide (a N-dealkylated product).

RopivacaineSupplier

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