Levobupivacaine hydrochlorideProduct ingredient for Levobupivacaine
- Name
- Levobupivacaine hydrochloride
- Drug Entry
- Levobupivacaine
Levobupivacaine is an amino-amide local anaesthetic drug belonging to the family of n-alkylsubstituted pipecoloxylidide. It is the S-enantiomer of bupivacaine. Levobupivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Chirocaine. In particular, the specific levobupivacaine enantiomer is a worthwhile pursuit because it demonstrates less vasodilation and possesses a greater length of action in comparison to bupivacaine. It is approximately 13 per cent less potent (by molarity) than racemic bupivacaine.Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children. When administered appropriately, the occurrence of adverse effects is not anticipated much if at all. In general, the majority of potential adverse effects are predominantly associated with inappropriate administration methods that may cause systemic exposure and/or toxicity associated with overexposure to an anesthetic. Regardless, allergic reactions may also occur - although only rarely.
- Accession Number
- DBSALT000834
- Structure
Structure for Levobupivacaine hydrochloride (DBSALT000834)
- Synonyms
- Levobupivacaine HCl
- UNII
- J998RDZ51I
- CAS Number
- 27262-48-2
- Weight
- Average: 324.889
Monoisotopic: 324.196841267 - Chemical Formula
- C18H29ClN2O
- InChI Key
- SIEYLFHKZGLBNX-NTISSMGPSA-N
- InChI
- InChI=1S/C18H28N2O.ClH/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H/t16-;/m0./s1
- IUPAC Name
- (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboximidic acid hydrochloride
- SMILES
- Cl.[H][C@]1(CCCCN1CCCC)C(O)=NC1=C(C)C=CC=C1C
- External Links
- PubChem Compound
- 117965
- ChemSpider
- 105409
- ChEBI
- 31772
- ChEMBL
- CHEMBL1200749
- Wikipedia
- Levobupivacaine
- Predicted Properties
Property Value Source Water Solubility 0.0267 mg/mL ALOGPS logP 3.71 ALOGPS logP 2.55 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 3.22 Chemaxon pKa (Strongest Basic) 8.8 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 35.83 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 90.95 m3·mol-1 Chemaxon Polarizability 34.93 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon