8485. Sibutramine

Nomenclature

CAS number: 106650-56-0
1-(4-Chlorophenyl)-N,N-dimethyl-α-(2-methylpropyl)cyclobutanemethanamine; N-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl-N,N-dimethylamine.
C17H26ClN; mol wt 279.85.
C 72.96%, H 9.36%, Cl 12.67%, N 5.01%.

Description and references

Serotonin and noradrenaline reuptake inhibitor (SNRI); decreases calorie intake and increases energy expenditure. Prepn: J. E. Jeffery et al., DE 3212682; idem, US 4929629 (1982, 1990 both to Boots). Clinical trial in obesity: C. Hanotin et al., Int. J. Obes. 22, 32 (1998). Review of pharmacology and mechanism of action: D. J. Heal et al., ibid. Suppl. 1, S18-S28.

Chemical structure

Derivative

Hydrochloride monohydrate.

Nomenclature

CAS number: 125494-59-9
BTS-54524; Reductil (Knoll); Meridia (Knoll).
C17H26ClN.HCl.H2O; mol wt 334.32.
C 61.07%, H 8.74%, Cl 21.21%, N 4.19%, O 4.79%.

Properties

Crystals from water, mp 193-195.5°. Partition coefficient (octanol/water): 30.9 (pH 5.0). Soly in water: 2.9 mg/ml at pH 5.2.

Note

This is a controlled substance (stimulant): 21 CFR, 1308.14.

Therapeutic Category

Antiobesity agent.

Keywords

Anorexic; Antiobesity Agent; Serotonin Noradrenaline Reuptake Inhibitor (SNRI)