CHEBI:8890 - (S)-ropivacaine

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ChEBI Name (S)-ropivacaine
ChEBI ID CHEBI:8890
ChEBI ASCII Name (S)-ropivacaine
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:718203
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Formula C17H26N2O
Net Charge 0
Average Mass 274.40110
Monoisotopic Mass 274.205
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
SMILES CCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
Roles Classification
Application(s): local anaesthetic
Any member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.
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ChEBI Ontology
Outgoing (S)-ropivacaine (CHEBI:8890) has role local anaesthetic (CHEBI:36333)
(S)-ropivacaine (CHEBI:8890) is a piperidinecarboxamide (CHEBI:48592)
(S)-ropivacaine (CHEBI:8890) is a ropivacaine (CHEBI:60802)
Incoming (S)-ropivacaine hydrochloride (anhydrous) (CHEBI:60803) has part (S)-ropivacaine (CHEBI:8890)
IUPAC Name
(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
INNs Sources
ropivacaina ChemIDplus
ropivacaine ChemIDplus
ropivacainum ChemIDplus
Synonyms Sources
(−)-1-propyl-2',6'-dimethyl-2-piperidylcarboxyanilide ChemIDplus
(−)-1-propyl-2',6'-pipecoloxylidide ChemIDplus
(S)-(−)-1-propyl-2',6'-pipecoloxylidide ChEBI
L-N-n-propylpipecolic acid-2,6-xylidide ChEBI
Ropivacaine KEGG COMPOUND
Database Links Databases
2403 DrugCentral
C07532 KEGG COMPOUND
D08490 KEGG DRUG
DB00296 DrugBank
LSM-5619 LINCS
Ropivacaine Wikipedia
WO8500599 Patent
View more database links
Registry Numbers Types Sources
5421606 Reaxys Registry Number Reaxys
84057-95-4 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
19586686 PubMed citation ChEMBL
Last Modified
22 February 2017
General Comment
2010-12-13 Note that the name ropivacaine refers to both the racemate and the marketed S-enantiomer. The hydrochloride hydrate of (S)-ropivacaine is commonly used for local anaesthesia, including infiltration, nerve block, epidural and intrathecal anaesthesia.