R0283

Ropivacaine hydrochloride monohydrate

≥98% (HPLC)

• Synonym(s): (2S)-N-(2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide hydrochloride monohydrate, (S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride monohydrate, Naropin hydrochloride monohydrate
• Empirical Formula (Hill Notation): C₁₇H₂₆N₂O · HCl · H₂O
• CAS Number: 132112-35-7
• Molecular Weight: 328.88
• MDL number: MFCD00946578
• UNSPSC Code: 12352203
• PubChem Substance ID: 329823983
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• optical activity: [α]/D -9 to -12, c = 1 in methanol
• storage condition: desiccated
• color: white to off-white
• solubility: H₂O: 5 mg/mL, clear
• originator: AstraZeneca
• storage temp.: 2-8°C
• SMILES string: O.Cl.CCCN1CCCC[C@H]1C(=O)Nc2c(C)cccc2C
• InChI: 1S/C17H26N2O.ClH.H2O/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);1H;1H2/t15-;;/m0../s1
• InChI key: VSHFRHVKMYGBJL-CKUXDGONSA-N

Description

General description

Ropivacaine has lidocaine-related structure with tertiary amine side chains. It is a pure S(-)enantiomer with a propyl group on the piperidine nitrogen atom.

Application

Ropivacaine hydrochloride monohydrate has been used as an analyte in tandem mass spectrometry and as an amide-based local anaesthetic to test its effect on breast cancer cell methylation.

Biochem/physiol Actions

Local anaesthetic with less cardiotoxicity than bupivacaine; causes reversible blockade of impulse propagation along nerve fibres by preventing the inward movement of sodium ions through the cell membrane of the nerve fibers.

Ropivacaine less lipophilic as compared with bupivacaine. It is metabolized in the liver by the enzyme cytochrome P4501A2. Ropivacaine elicits less central nervous system (CNS) toxicity and is used as a local anaesthetic during postoperative and labour pain.

Features and Benefits

This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H318
• Precautionary Statements: P280 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable