1495. Bupivacaine

Nomenclature

CAS number: 2180-92-9
1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide; 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.
C18H28N2O; mol wt 288.43.
C 74.95%, H 9.78%, N 9.71%, O 5.55%.

Description and 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).

Chemical structure

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.

Derivative

Hydrochloride monohydrate.

Nomenclature

CAS number: 14252-80-3
AH-2250; LAC-43; Carbostesin (AstraZeneca); Marcaine (AstraZeneca); Sensorcaine (AstraZeneca).
C18H28N2O.HCl.H2O; mol wt 342.90.
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).

Derivative

(-)-Form.

Nomenclature

CAS number: 27262-47-1
Levobupivacaine; (S)-bupivacaine.

Properties

Crystals from isopropanol, mp 135-137°. [α]D25 -80.9° (c = 5 in methanol).

Derivative

(-)-Form hydrochloride.

Nomenclature

CAS number: 27262-48-2
Chirocaine (Abbott).
C18H28N2O.HCl; mol wt 324.89.
C 66.54%, H 9.00%, N 8.62%, O 4.92%, Cl 10.91%.

Properties

mp 255-257°. [α]D25 -12.3° (c = 2 in water).

Therapeutic Category

Anesthetic (local).

Keywords

Anesthetic (Local)