Ropivacaine
Title: Ropivacaine
CAS Registry Number: 84057-95-4
CAS Name: (2S)-N-(2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide
Additional Names: (S)-(-)-1-propyl-2¢,6¢-pipecoloxylidide; l-N-n-propylpipecolic acid-2,6-xylidide
Manufacturers' Codes: LEA-103
Molecular Formula: C17H26N2O
Molecular Weight: 274.40
Percent Composition: C 74.41%, H 9.55%, N 10.21%, O 5.83%
Literature 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°. [a]D25 -82.0° (c = 2 in methanol). pKa 8.16. Distribution coefficient (1-octanol/aq buffer, pH 7.4): 115.0.
Melting point: mp 144-146°
pKa: pKa 8.16
Optical Rotation: [a]D25 -82.0° (c = 2 in methanol)
 
Derivative Type: Hydrochloride
CAS Registry Number: 98717-15-8
Trademarks: Naropin (AstraZeneca)
Molecular Formula: C17H26N2O.HCl
Molecular Weight: 310.86
Percent Composition: C 65.68%, H 8.75%, N 9.01%, O 5.15%, Cl 11.40%
Properties: Crystals from isopropyl alcohol, mp 260-262°. [a]D25 -6.6° (c = 2 in water).
Melting point: mp 260-262°
Optical Rotation: [a]D25 -6.6° (c = 2 in water)
 
Derivative Type: Hydrochloride monohydrate
CAS Registry Number: 132112-35-7
Properties: Crystals from acetone + water, mp 269.5-270.6°. [a]D20 -7.28° (c = 2 in water).
Melting point: mp 269.5-270.6°
Optical Rotation: [a]D20 -7.28° (c = 2 in water)
 
Therap-Cat: Anesthetic (local).
Keywords: Anesthetic (Local).

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