Serdexmethylphenidate

Serdexmethylphenidate (codenamed KP484) is a derivative of dexmethylphenidate created by pharmaceutical company KemPharm. The compound is under investigation for the treatment of ADHD in children, adolescents, and adults as of 2020.[1] Serdexmethylphenidate is a prodrug which has a delayed onset of action and a prolonged duration of effects compared to dexmethylphenidate, its parent compound.

Serdexmethylphenidate

Clinical data
Routes of administration	Oral
Legal status
Legal status	Investigational
Identifiers
IUPAC name (1-((((R)-2-((R)-2-methoxy-2-oxo-1-phenylethyl)piperidine-1-carbonyl)oxy)methyl)pyridin-1-ium-3-carbonyl)-L-serinate chloride
CAS Number	1996626-30-2
PubChem CID	134823897
ChemSpider	81368035
UNII	FN54BT298Y
KEGG	D11401
ChEMBL	ChEMBL4298139
Chemical and physical data
Formula	C25H30ClN3O8
Molar mass	535.98 g·mol^−1
3D model (JSmol)	Interactive image
SMILES COC(=O)[C@@H]([C@H]1CCCCN1C(=O)OC[N+]2=CC=CC(=C2)C(=O)N[C@@H](CO)C(=O)O)C3=CC=CC=C3.[Cl-]
InChI InChI=1S/C25H29N3O8.ClH/c1-35-24(33)21(17-8-3-2-4-9-17)20-11-5-6-13-28(20)25(34)36-16-27-12-7-10-18(14-27)22(30)26-19(15-29)23(31)32;/h2-4,7-10,12,14,19-21,29H,5-6,11,13,15-16H2,1H3,(H-,26,30,31,32);1H/t19-,20+,21+;/m0./s1 Key:GONQEUJYYMYNMN-HWAJWLCKSA-N
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Formulations

Due to serdexmethylphenidate's delayed onset and prolonged duration of effects, several dosage forms containing serdexmethylphenidate have been investigated for use as long-acting psychostimulants in the treatment of ADHD. Under the developmental codename KP484, serdexmethylphenidate has been investigated as a "super-extended duration" psychostimulant, with therapeutic efficacy lasting up to 16 hours following oral administration. Serdexmethylphenidate has also been co-formulated with immediate-release dexmethylphenidate under the codename KP415. Co-formulation of serdexmethylphenidate with dexmethylphenidate allows for a more rapid onset of action while still retaining up to 13 hours of therapeutic efficacy.[2]

In 2011, MonoSol Rx entered into a partnership with KenPharm to develop oral films containing KP415.[3]

Abuse potential

The abuse potential of serdexmethylphenidate is theorized to be lower than other psychostimulants because serdexmethylphenidate is an inactive prodrug of dexmethylphenidate, and must undergo enzymatic metabolism prior to exerting any stimulant effects.[4] Common routes of administration used during the abuse of psychostimulants such as insufflation and intravenous injection have little impact on the pharmacokinetics and metabolism of serdexmethylphenidate and do not result in a faster onset of action.[5]

See also

• Dexmethylphenidate

References

1. "KemPharm's KP415 and Serdexmethylphenidate (SDX) Prodrug to be Featured in Multiple Sessions at the AACAP 2020 Virtual Meeting". www.globenewswire.com.
2. Mickle T. "Prodrugs for ADHD Treatments: Opportunities & Potential to Fill Unmet Medical Needs" (PDF). Retrieved 15 November 2020.
3. Van Arnum P (1 March 2012). "Meeting Solubility Challenges". Pharmaceutical Technology. 2012 (2): S6–S8. Retrieved 15 November 2020.
4. Mickle T. "Prodrugs for ADHD Treatments: Opportunities & Potential to Fill Unmet Medical Needs" (PDF). Retrieved 15 November 2020.
5. Braeckman R (1 October 2018). "Human Abuse Potential of Intravenous Serdexmethylphenidate (SDX), A Novel Prodrug of D-Methylphenidate, in Recreational Stimulant Abusers". Journal of the American Academy of Child & Adolescent Psychiatry. 57 (10): 176. doi:10.1016/j.jaac.2018.09.141. Retrieved 15 November 2020.