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XP-21279

Clinical data
Other names	XP21279
Routes of administration	Oral
Drug class	Dopamine precursor; Dopamine receptor agonist
Identifiers
IUPAC name oxypropan-2-yl] benzoate
CAS Number	1426325-45-2
PubChem CID	11559525
DrugBank	DB06319
ChemSpider	9734299
ChEMBL	ChEMBL4763200
Chemical and physical data
Formula	C19H21NO6
Molar mass	359.378 g·mol
3D model (JSmol)	Interactive image
SMILES C(COC(=O)(CC1=CC(=C(C=C1)O)O)N)OC(=O)C2=CC=CC=C2
InChI InChI=1S/C19H21NO6/c1-12(26-18(23)14-5-3-2-4-6-14)11-25-19(24)15(20)9-13-7-8-16(21)17(22)10-13/h2-8,10,12,15,21-22H,9,11,20H2,1H3/t12-,15+/m1/s1 Key:AKUWZLYXAADOTQ-DOMZBBRYSA-N

XP-21279 is a sustained-release levodopa (L-DOPA) prodrug and hence a dopamine precursor and non-selective dopamine receptor agonist which was under development for the treatment of Parkinson's disease. It is taken by mouth.

Pharmacology

The drug is said to add a five-carbon ester conjugate to levodopa that allows it to be actively transported by high-capacity nutrient transporters throughout the entire gastrointestinal tract. Subsequently, it is rapidly converted into levodopa by carboxylesterases. Levodopa itself can only be transported by a short section of the small intestine and hence XP-21279 allows more time for levodopa to be absorbed, in turn resulting in an increased duration and possibly reduced fluctuations in dopamine levels between levodopa doses.

Clinical studies

As of June 2015, XP-21279 was in phase 2 clinical trials. As of May 2022, there have been no further developmental updates. It was reported in 2018 that development of the drug had been discontinued several years prior. A 2019 review reported that results were conflicting in phase 2 trials and that this likely resulted in the discontinuation of the drug's development.

Chemistry

Many sources do not report the chemical structure of XP-21279, suggesting that its exact structure has not been disclosed. However, one source appears to report its chemical structure.

See also

• Etilevodopa
• Foslevodopa
• Melevodopa

References

1. ^ Hauser RA (2011). "Future treatments for Parkinson's disease: surfing the PD pipeline". The International Journal of Neuroscience. 121 Suppl 2: 53–62. doi:10.3109/00207454.2011.620195. PMID 22035030.
2. ^ Ondo W (October 2014). "IPX066 , a mixed immediate/sustained-release levodopa preparation for Parkinson's disease". Expert Opinion on Pharmacotherapy. 15 (14): 2081–2085. doi:10.1517/14656566.2014.950224. PMID 25146967.
3. ^ Freitas ME, Ruiz-Lopez M, Fox SH (November 2016). "Novel Levodopa Formulations for Parkinson's Disease". CNS Drugs. 30 (11): 1079–1095. doi:10.1007/s40263-016-0386-8. PMID 27743318.
4. ^ "XP 21279". AdisInsight. Springer Nature Switzerland AG. 26 May 2022. Retrieved 27 September 2024.
5. ^ Hengartner D, Fernandez HH (February 2019). "The next chapter in symptomatic Parkinson disease treatments". Parkinsonism & Related Disorders. 59. Elsevier BV: 39–48. doi:10.1016/j.parkreldis.2019.01.002. PMID 30661840.
6. ^ Cacciatore I, Ciulla M, Marinelli L, Eusepi P, Di Stefano A (April 2018). "Advances in prodrug design for Parkinson's disease". Expert Opinion on Drug Discovery. 13 (4): 295–305. doi:10.1080/17460441.2018.1429400. PMID 29361853.
7. "XP21279: Uses, Interactions, Mechanism of Action". DrugBank Online. 19 March 2008. Retrieved 27 September 2024.
8. "Delving into the Latest Updates on XP-21279 with Synapse". Synapse. 20 September 2024. Retrieved 27 September 2024.
9. "XP 21279". PubChem. Retrieved 27 September 2024.
10. Markovic M, Deodhar S, Machhi J, Yeapuri P, Saleh M, J Edagwa B, et al. (February 2022). "Prodrug Therapies for Infectious and Neurodegenerative Diseases". Pharmaceutics. 14 (3): 518. doi:10.3390/pharmaceutics14030518. PMC 8953076. PMID 35335894.
11. Haddad F, Sawalha M, Khawaja Y, Najjar A, Karaman R (December 2017). "Dopamine and Levodopa Prodrugs for the Treatment of Parkinson's Disease". Molecules. 23 (1): 40. doi:10.3390/molecules23010040. PMC 5943940. PMID 29295587.

• Abandoned drugs
• Antiparkinsonian agents
• Benzoate esters
• Catecholamines
• Dopamine agonists
• Esters
• Monoamine precursors
• Prodrugs