General
Preferred name
lisdexamfetamine
Synonyms
Lisdexamfetamine (mesylate) (exempt preparation) ()
Vyvanse ()
lisdexamfetamine mesilate ()
NRP-104 ()
NRP104 ()
Elvanse ()
Lisdexamfetamine dimesilate ()
Elvanse Adult ()
SPD489 ()
Lisdexamphetamine dimesilate ()
SPD-489 ()
Tyvense ()
Lisdexamfetamine dimethanesulfonate ()
LISDEXAMFETAMINE DIMESYLATE ()
Lisdexamphetamine ()
Lisdexanfetamina ()
L-lysine-dextroamphetamine ()
Lisdexamfetamine (mesylate) ()
Lisdexamfetamine (mesylate) (CRM) ()
P&D ID
PD009934
CAS
608137-33-3
608137-32-2
Tags
available
prodrug
drug
Approved by
FDA
PMDA
First approval
2007
Drug indication
Attention deficit hyperactivity disorder
Drug Status
approved
investigational
Max Phase
4.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION
This drug is a prodrug of dexamphetamine. The amphetamine is released more slowly from this prodrug than by administering active amphetamine directly.
(GtoPdb)
ABSORPTION
After oral administration, lisdexamfetamine is rapidly absorbed from the gastrointestinal tract [FDA label], [F2355].; ; **Chewable tablet form:** After a single dose of 60 mg a chewable tablet in healthy subjects under fasted conditions, the Tmax of lisdexamfetamine and dextroamphetamine was reached at about 1 hour and 4.4 hour post administration, respectively [FDA label].; ; **Capsule form:** Following single-dose oral (30 mg, 50 mg, or 70 mg) in patients ages 6 to 12 years with ADHD under fasted conditions, Tmax of lisdexamfetamine and dextroamphetamine was reached at about 1 hour and 3.5 hours post administration, respectively [FDA label].
HALF-LIFE
The mean plasma elimination half-life of dextroamphetamine was about 12 hours after oral administration of lisdexamfetamine dimesylate [FDA label]. ; ; The plasma elimination half-life of lisdexamfetamine alone averaged less than one hour in studies of lisdexamfetamine dimesylate administered in volunteer subjects [FDA label].
TOXICITY
**Acute toxicity**: Symptoms of acute overdosage with amphetamines include restlessness, tremor, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations, panic states, hyperpyrexia, and rhabdomyolysis. Fatigue and depression generally follow the symptoms central nervous system stimulation. Cardiovascular effects include arrhythmias, hypertension or hypotension and/or circulatory collapse. Gastrointestinal symptoms include nausea, vomiting, diarrhea, and abdominal cramps. Lethal poisoning is usually preceded by convulsions and coma [FDA label]. Prescribers should consider that serious cardiovascular (CV) events have been reported with this class of drugs [F2355].; ; **Long-term effects**: Acute administration of high doses of amphetamine (d- or d,l-) has been shown to produce long-term neurotoxic effects, which include irreversible nerve fiber damage, in rodents. The relevance of these findings to humans is currently unknown [FDA label].; ; **Oral LD50 (rat)**: 7,060 mg/kg [MSDS]; ; **Oral LD50 (mouse)**: 3,450 mg/kg [MSDS]; ; **Use in Pregnancy**; ; This drug is categorized as a Pregnancy Category C: Animal studies have shown risk to the fetus, there are no controlled studies in women, or studies in women and animals are not available [FDA label].
INDICATION
For the treatment of Attention-deficit/hyperactivity disorder (ADHD) and for moderate to severe binge eating disorder in adults [FDA label], [A40246].; ; This drug is not indicated for weight loss. Use of other sympathomimetic drugs for weight loss is associated with serious cardiovascular effects. The safety and effectiveness of this drug for the treatment of obesity have not yet been determined [FDA label].;
PHARMACODYNAMICS
Lisdexamfetamine dimesylate is a prodrug of _d-amphetamine_. Amphetamines are non-catecholamine sympathomimetic amines with CNS stimulating properties [FDA label]. This agent works primarily by inducing the release of the neurotransmitters dopamine and norepinephrine from their storage areas in presynaptic nerve terminals [F2366]. Both of these transmitters contribute to alertness, increased concentration, in addition to effort and motivation.;
ROE
After the oral administration of a 70mg dose of radiolabeled lisdexamfetamine dimesylate to six healthy subjects, about 96% of the oral dose radioactivity was recovered in the urine and only 0.3% recovered in the feces [FDA label], [F2355].;
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
13
ChEMBL Approved Drugs
ChEMBL Drugs
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Guide to Pharmacology
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
ReFrame library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
48
Molecular Weight
263.2
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
3
Rotatable Bonds
8
Ring Count
1
Aromatic Ring Count
1
cLogP
1.19
TPSA
81.14
Fraction CSP3
0.53
Chiral centers
2.0
Largest ring
6.0
QED
0.62
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Biosynthetic Origin
Alkaloid
Therapeutic Indication
ADHD
Therapeutic Class
CNS & PNS
Source data
