8258. Ropivacaine
Nomenclature
CAS number: 84057-95-4
(2S)-N-(2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide; (S)-(-)-1-propyl-2′,6′-pipecoloxylidide; l-N-n-propylpipecolic acid-2,6-xylidide; LEA-103. C17H26N2O; mol wt 274.40.
C 74.41%, H 9.55%, N 10.21%, O 5.83%.
Description and references
Prepn: A. F. Thuresson, C. Bovin, WO 8500599 (1985 to Apothekernes); H.-J. Federsel et al., Acta Chem. Scand. B41, 757 (1987). Physicochemical properties: G. R. Strichartz et al., Anesth. Analg. 71, 158 (1990). HPLC determn in human plasma: Z. Yu et al., J. Chromatogr. B 654, 221 (1994). In vitro metabolism: Y. Oda et al., Anesthesiology 82, 214 (1995). Clinical pharmacokinetics: D. J. Kopacz et al., ibid. 81, 1139 (1994). Toxicity study in sheep: A. C. Santos et al., ibid. 82, 734 (1995). Clinical evaluation in relief of surgical pain: I. Cederholm et al., Reg. Anesth. 19, 18 (1994); B. Johansson et al., Anesth. Analg. 78, 210 (1994); labor pain: R. Stienstra et al., ibid. 80, 285 (1995).
Properties
Crystals from toluene, mp 144-146°. [α]D25 -82.0° (c = 2 in methanol). pKa 8.16. Distribution coefficient (1-octanol/aq buffer, pH 7.4): 115.0.Derivative
Hydrochloride.Nomenclature
CAS number: 98717-15-8
Naropin (AstraZeneca). C17H26N2O.HCl; mol wt 310.86.
C 65.68%, H 8.75%, N 9.01%, O 5.15%, Cl 11.40%.
Properties
Crystals from isopropyl alcohol, mp 260-262°. [α]D25 -6.6° (c = 2 in water).Derivative
Hydrochloride monohydrate.Nomenclature
CAS number: 132112-35-7
Properties
Crystals from acetone + water, mp 269.5-270.6°. [α]D20 -7.28° (c = 2 in water).Therapeutic Category
Anesthetic (local).
Keywords
Anesthetic (Local)