6464. Neostigmine

Nomenclature

CAS number: 59-99-4
3-[[(Dimethylamino)carbonyl]oxy]-N,N,N-trimethylbenzenaminium; (3-dimethylcarbamoxyphenyl) trimethylammonium; synstigmin; proserine.
[C12H19N2O2]+.

Description and references

Reversible cholinesterase inhibitor. Synthesis: Aeschlimann, US 1905990 (1933 to Hoffmann-La Roche); Yanagisawa, JP 51 3071 (1951), C.A. 47, 4908g (1953). Pharmacology and pharmacokinetics: T. N. Calvey et al., Br. J. Clin. Pharmacol. 7, 149 (1979). Comprehensive description: A. A. Al-Badr, M. Tariq, Anal. Profiles Drug Subs. 16, 403-444 (1987). HPLC determn in plasma and CSF: F. Varin et al., J. Chromatogr. B 723, 319 (1999). Clinical evaluation in treatment of acute colonic pseudo-obstruction: R. J. Ponec et al., N. Engl. J. Med. 341, 137 (1999). Clinical comparison with edrophonium for neuromuscular block reversal: M. Naguib, W. Riad, Can. J. Anaesth. 47, 1074 (2000).

Chemical structure

Derivative

Bromide.

Nomenclature

CAS number: 114-80-7
Prostigmin (tabl.) (Valeant).
C12H19BrN2O2; mol wt 303.20.
C 47.54%, H 6.32%, Br 26.35%, N 9.24%, O 10.55%.

Properties

White, crystalline powder with bitter taste. Crystals from alcohol + ether, dec ≈167°. One gram dissolves in ≈1 ml water. Sol in alc.

Derivative

Methyl sulfate.

Nomenclature

CAS number: 51-60-5
Intrastigmina (Lusofarmaco); Normastigmin (Sigmapharm); Prostigmin (amp.) (Valeant).
C13H22N2O6S; mol wt 334.39.
C 46.69%, H 6.63%, N 8.38%, O 28.71%, S 9.59%.

Properties

Crystals from alc, mp 142-145°. One gram dissolves in ≈10 ml water, less sol in alcohol. LD50 in mice (mg/kg): 0.16 i.v.; 0.42 s.c.; 7.5 orally. See: L. O. Randall, G. Lehmann, J. Pharmacol. Exp. Ther. 99, 16 (1950).

Therapeutic Category

Cholinergic; antidote (curare). In treatment of myasthenia gravis. Reversal agent for neuromuscular blocking drugs.

Therapeutic Category (Veterinary)

Cholinergic; antidote (curare). In treatment of myasthenia gravis. Reversal agent for neuromuscular blocking drugs.

Keywords

Cholinergic; Antimyasthenic; Antidote (Curare); Cholinesterase Inhibitor; Neuromuscular Block Reversant