10317. Lisdexamfetamine

Nomenclature

CAS number: 608137-32-2
(2S)-2,6-Diamino-N-[(1S)-1-methyl-2-phenylethyl]hexanamide; l-lysine-d-amphetamine.
C15H25N3O; mol wt 263.38.
C 68.40%, H 9.57%, N 15.95%, O 6.07%.

Description and references

Inactive prodrug in which dextroamphetamine is covalently bound to l-lysine; the amide bond is hydrolyzed during metabolism to release active d-amphetamine. Prepn: T. Mickle et al., WO 05032474; eidem, US 05054561 (both 2005 to New River Pharm.). Evaluation of cytochrome P450 interations: S. Krishnan, S. Moncrief, Drug Metab. Dispos. 35, 180 (2007) DOI PubMed. Pharmacokinetics in adults: S. Krishnan, Y. Zhang, J. Clin. Pharmacol. 48, 293 (2008) DOI PubMed. Clinical efficacy in pediatric ADHD: J. Biederman et al., Clin. Ther. 29, 450 (2007) DOI PubMed. Review of pediatric pharmacology and clinical experience: S. K. A. Blick, G. M. Keating, Pediatr. Drugs 9, 129-135 (2007) DOI PubMed; of development and clinical experience: S. V. Faraone, Expert Opin. Pharmacother. 9, 1565-1574 (2008) DOI PubMed.

Chemical structure

Properties

Golden colored solid from MeOH, mp 120-122°.

Derivative

Dimethanesulfonate.

Nomenclature

CAS number: 608137-33-3
Lisdexamfetamine dimesylate; NRP-104; Vyvanse (Shire).
C15H25N3O.2CH4O3S; mol wt 455.59.
C 44.82%, H 7.30%, N 9.22%, O 24.58%, S 14.08%.

Properties

White to off-white powder, mp 120-122°. Soly in water: 792 mg/ml.

Therapeutic Category

In treatment of attention deficit hyperactivity disorder (ADHD).

Keywords

CNS Stimulant