Bupivacaine
Title: Bupivacaine
CAS Registry Number: 2180-92-9
CAS Name: 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide
Additional Names: dl-1-butyl-2¢,6¢-pipecoloxylidide; 1-n-butyl-2¢,6¢-dimethyl-2-piperidinecarboxanilide; dl-N-n-butylpipecolic acid 2,6-xylidide; 1-butyl-2-(2,6-xylylcarbamoyl)piperidine; dl-1-n-butylpiperidine-2-carboxylic acid 2,6-dimethylanilide
Molecular Formula: C18H28N2O
Molecular Weight: 288.43
Percent Composition: C 74.95%, H 9.78%, N 9.71%, O 5.55%
Literature References: Prepn: B. Ekenstam et al., Acta Chem. Scand. 11, 1183 (1957); B. T. Ekenstam, B. G. Pettersson, US 2955111 (1960 to AB Bofors). Resolution of isomers: B. F. Tullar, J. Med. Chem. 14, 891 (1971). Stereospecific synthesis: B. Adger et al., Tetrahedron Lett. 37, 6399 (1996). Pharmacology of racemate: F. Henn, R. Brattsand, Acta Anaesthesiol. Scand. Suppl. 21, 9 (1966), C.A. 66, 17863u (1967); of isomers: F. P. Luduena et al., Arch. Int. Pharmacodyn. 200, 359 (1972). Clinical pharmacokinetics: D. W. Blake et al., Anaesth. Intensive Care 22, 522 (1994). Comprehensive description: T. D. Wilson, Anal. Profiles Drug Subs. 19, 59-94 (1990). Review of use in spinal anesthesia: Acta Anaesthesiol. Scand. 35, 1-10 (1991). Review of pharmacology and clinical efficacy of levobupivacaine: K. J. McClellan, C. M. Spencer, Drugs 56, 355-362 (1998).
Properties: mp 107.5-108°. pKa 8.09; also reported as 8.17. Partition coefficient: (oleyl alcohol/water) 1565; (n-heptane/pH 7.4 buffer) 27.5.
Melting point: mp 107.5-108°
pKa: pKa 8.09; also reported as 8.17
Log P: Partition coefficient: (oleyl alcohol/water) 1565; (n-heptane/pH 7.4 buffer) 27.5
 
Derivative Type: Hydrochloride monohydrate
CAS Registry Number: 14252-80-3
Manufacturers' Codes: AH-2250; LAC-43
Trademarks: Carbostesin (AstraZeneca); Marcaine (AstraZeneca); Sensorcaine (AstraZeneca)
Molecular Formula: C18H28N2O.HCl.H2O
Molecular Weight: 342.90
Percent Composition: C 63.05%, H 9.11%, N 8.17%, O 9.33%, Cl 10.34%
Properties: White, odorless crystalline powder. mp 258.5°. Slightly sol in acetone, chloroform, ether. Soly (mg/ml): water 40; alcohol 125. LD50 in mice (mg/kg): 7.8 i.v., 82 s.c. (Henn, Brattsand).
Melting point: mp 258.5°
Toxicity data: LD50 in mice (mg/kg): 7.8 i.v., 82 s.c. (Henn, Brattsand)
 
Derivative Type: (-)-Form
CAS Registry Number: 27262-47-1
Additional Names: Levobupivacaine; (S)-bupivacaine
Properties: Crystals from isopropanol, mp 135-137°. [a]D25 -80.9° (c = 5 in methanol).
Melting point: mp 135-137°
Optical Rotation: [a]D25 -80.9° (c = 5 in methanol)
 
Derivative Type: (-)-Form hydrochloride
CAS Registry Number: 27262-48-2
Trademarks: Chirocaine (Abbott)
Molecular Formula: C18H28N2O.HCl
Molecular Weight: 324.89
Percent Composition: C 66.54%, H 9.00%, N 8.62%, O 4.92%, Cl 10.91%
Properties: mp 255-257°. [a]D25 -12.3° (c = 2 in water).
Melting point: mp 255-257°
Optical Rotation: [a]D25 -12.3° (c = 2 in water)
 
Therap-Cat: Anesthetic (local).
Keywords: Anesthetic (Local).

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