XP-21279

XP-21279
Clinical data
Other namesXP21279
Routes of
administration		Oral[1][2][3]
Drug classDopamine precursor; Dopamine receptor agonist
Identifiers
  • [(2R)-1-[(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoyl]oxypropan-2-yl] benzoate
CAS Number
PubChem CID
DrugBank
ChemSpider
ChEMBL
Chemical and physical data
FormulaC19H21NO6
Molar mass359.378 g·mol−1
3D model (JSmol)
  • C[C@H](COC(=O)[C@H](CC1=CC(=C(C=C1)O)O)N)OC(=O)C2=CC=CC=C2
  • 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.[4][1][3] It is taken by mouth.[1][2][3]

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.[2][3][5] Subsequently, it is rapidly converted into levodopa by carboxylesterases.[2][3][5] 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.[1][2][3]

Clinical studies

As of June 2015, XP-21279 was in phase 2 clinical trials.[4] As of May 2022, there have been no further developmental updates.[4] It was reported in 2018 that development of the drug had been discontinued several years prior.[6] 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.[5]

Chemistry

Many sources do not report the chemical structure of XP-21279, suggesting that its exact structure has not been disclosed.[7][8][9][6][10] However, one source appears to report its chemical structure.[11]

See also

References

  1. ^ a b c d 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. ^ a b c d e 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. ^ a b c d e f 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. ^ a b c "XP 21279". AdisInsight. Springer Nature Switzerland AG. 26 May 2022. Retrieved 27 September 2024.
  5. ^ a b c 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. ^ a b 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.