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Lisdexamfetamine

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Lisdexamfetamine
Clinical data
Other names(S)-2,6-diamino-N-[(S)-1-phenylpropan-2-yl]hexanamide
Pregnancy
category
  • C
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Bioavailability28%
MetabolismGastro-intestinal (initial); Hepatic (extensively CYP2D6) after conversion to d-amphetamine
Elimination half-life< 1 hour (prodrug molecule), 12-13 hours (d-amphetamine)
ExcretionRenal: ~2%
Identifiers
  • N-[(1S)-1-methyl-2-phenylethyl]-L-lysinamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H25N3O
Molar mass263.378 g/mol g·mol−1
  (verify)

Lisdexamfetamine (L-lysine-D-amphetamine; sold as Vyvanse) is a psychoactive drug and stimulant prodrug of the phenethylamine and amphetamine chemical classes. Its molecular structure consists of dextroamphetamine coupled with the essential amino acid L-lysine.

Lisdexamfetamine itself is inactive and acts as a prodrug to dextroamphetamine upon cleavage of the lysine portion of the molecule. It was developed for the intention of creating a longer-lasting and more difficult to abuse version of dextroamphetamine, as the requirement of conversion into dextroamphetamine in the gastrointestinal tract increases its duration and renders it ineffective upon any other ingestion routes than the oral route.[2] Intravenously administered lisdexamfetamine initially produced effects similar to placebo, and therefore intravenous abuse is completely ineffective; there is no increased onset or effect as occurs with IV administration of dextroamphetamine compared to oral use of the same. [3]

As opposed to Adderall, which contains roughly 75% dextroamphetamine and 25% levoamphetamine, lisdexamfetamine is a single-enantiomer (dextro) amphetamine formula. This pure formulation may reduce side effects, but certain individuals exhibit a better clinical response to the mixed isomer preparation.[4]

Dosage

70mg Vyvanse capsules

Lisdexamfetamine is available under the brand-name Vyvanse. Vyvanse comes in several different dosages (see table below). All of these dosages come in the form of 30 capsules, each of which contains the labeled dose to be taken once daily.[5]

Vyvanse dosage strengths available[5]
Strength Appearance Imprint (unique label)
20 milligrams Capsule with ivory colored body and cap NRP104 20 mg
30 milligrams Capsule with white colored body and orange colored cap NRP104 30 mg
40 milligrams Capsule with white colored body and cyan colored cap NRP104 40 mg
50 milligrams Capsule with white colored body and blue colored cap NRP104 50 mg
60 milligrams Capsule with aqua blue colored body and cap NRP104 60 mg
70 milligrams Capsule with blue colored body and orange colored cap NRP104 70 mg

A 25 mg Vyvanse capsule would be molecularly equivalent to a 10 mg Dexedrine Spansule (both are about 7.425mg dextroamphetamine base), although a 25 mg Vyvanse capsule is not commercially available.[citation needed] However, the molecular equivalence ratio does not mean that the respective doses of Vyvanse and Dexedrine XR (Spansule) are bioequivalent because the two formulations have slightly different pharmacokinetic profiles. For example, while the area under the curve for the aforementioned pharmaceuticals is equivalent, the peak exposure (Cmax) to the active compound dextroamphetamine is about 50% higher for Vyvanse than for Dexedrine XR.[6]

History

Vyvanse was developed by New River Pharmaceuticals, who were bought by Shire Pharmaceuticals shortly before lisdexamfetamine began being marketed. Vyvanse is approved by the U.S. Food and Drug Administration (FDA) for the treatment of attention-deficit hyperactivity disorder. Vyvanse pills are available in dosages of up to 70 mg (for 12 hours).[citation needed]

On April 23, 2008, Vyvanse received FDA approval for the adult population [7]. In a randomized, double-blind, four-week phase III trial in adult patients with ADHD, 30, 50 or 70mg/day of oral lisdexamfetamine caused a significantly greater improvement in ADHD-Rating Scale total score than placebo.[8]

On February 19, 2009, Health Canada approved 30 mg and 50 mg capsules of lisdexamfetamine for treatment of ADHD.[9]

Misuse potential

Lisdexamfetamine has potential for causing severe addiction, especially if used for long periods of time. Misuse of lisdexamfetamine may cause serious and potentially fatal cardiovascular abnormalities or even sudden death.[10]

Adverse side effects

See also: Dextroamphetamine effects

The side effects of lisdexamfetamine are similar to other amphetamine preparations.[5][11] Many individuals taking lisdexamfetamine will experience side effects, but for the majority the severity of the side effects is not severe. Lisdexamfetamine, like other amphetamines, can cause severe and possibly life-threatening side effects and even sudden death in sensitive individuals.[5][10]

In a clinical study for Vyvanse, 10% of patients taking lisdexamfetamine withdrew from the study due to adverse reactions compared to 1% taking placebo.[5]

Common side effects

Common side effects (side effects that have average rates of presentation; usually presenting in >5% of patients) of lisdexamfetamine use include:[5][10]

Severe side effects

Very infrequent but possibly severe side effects requiring immediate medical attention may be caused by lisdexamfetamine; these serious reactions include:[5][10]

See also

References

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ Lisdexamfetamine Dimesylate: A Prodrug Stimulant for the Treatment of ADHD in Children and Adults
  3. ^ Human pharmacology of intravenous lisdexamfetamine dimesylate: abuse liability in adult stimulant abusers.
  4. ^ "Vyvanse Vs. Adderall
  5. ^ a b c d e f g Vyvanse (Lisdexamfetamine Dimesylate) Drug Information: Uses, Side Effects, Drug Interactions and Warnings at RxList
  6. ^ FDA Approval of Vyvanse - Pharmacological Reviews
  7. ^ FDA Adult Approval of Vyvanse - FDA Label and Approval History
  8. ^ Weber J, Siddiqui, MA. [1].CNSDrugs 2009; 23(5): 419-425.doi: 10.2165/00023210-200923050-00005.
  9. ^ Health Canada Notice of Compliance - Vyvanse. February 19, 2009, retrieved on March 9, 2009.
  10. ^ a b c d Lisdexamfetamine Capsules Facts and Comparisons at Drugs.com
  11. ^ Dextroamphetamine rxlist information
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