Lumicitabine

Lumicitabine (ALS-8176) is an antiviral drug which was developed as a treatment for respiratory syncytial virus (RSV) and human metapneumovirus (hMPV). It acts as an RNA polymerase inhibitor.[1] While it showed promise in early clinical trials,[2][3] poor results in Phase IIb trials led to it being discontinued from development for treatment of RSV.[4] Research continues to determine whether it may be useful for the treatment of diseases caused by other RNA viruses, and it has been found to show activity against Nipah virus.[5]

Lumicitabine
Clinical data
Trade namesLumicitabine
Legal status
Legal status
Identifiers
IUPAC name
  • [(2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(chloromethyl)-4-fluoro-3-(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.245.433
Chemical and physical data
FormulaC18H25ClFN3O6
Molar mass433.9 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)C(=O)OC[C@@]1([C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)N)F)OC(=O)C(C)C)CCl
InChI
  • InChI=1S/C18H25ClFN3O6/c1-9(2)15(24)27-8-18(7-19)13(28-16(25)10(3)4)12(20)14(29-18)23-6-5-11(21)22-17(23)26/h5-6,9-10,12-14H,7-8H2,1-4H3,(H2,21,22,26)/t12-,13+,14-,18-/m1/s1
  • Key:MJVKYGMNSQJLIN-KYZVSKTDSA-N

See also

References
  1. Wang G, Deval J, Hong J, Dyatkina N, Prhavc M, Taylor J, Fung A, Jin Z, Stevens SK, Serebryany V, Liu J, Zhang Q, Tam Y, Chanda SM, Smith DB, Symons JA, Blatt LM, Beigelman L (February 2015). "Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection". Journal of Medicinal Chemistry. 58 (4): 1862–78. doi:10.1021/jm5017279. PMID 25667954.
  2. Brendish NJ, Clark TW (December 2017). "Antiviral treatment of severe non-influenza respiratory virus infection". Current Opinion in Infectious Diseases. 30 (6): 573–578. doi:10.1097/QCO.0000000000000410. PMID 29095723. S2CID 2662061.
  3. Patel K, Kirkpatrick CM, Nieforth KA, Chanda S, Zhang Q, McClure M, Fry J, Symons JA, Blatt LM, Beigelman L, DeVincenzo JP, Huntjens DR, Smith PF (February 2019). "Respiratory syncytial virus-A dynamics and the effects of lumicitabine, a nucleoside viral replication inhibitor, in experimentally infected humans". The Journal of Antimicrobial Chemotherapy. 74 (2): 442–452. doi:10.1093/jac/dky415. PMID 30376079.
  4. Taylor P (18 October 2018). "Johnson & Johnson takes $630M hit on RSV drug bought with Alios". fiercebiotech.com.
  5. Lo MK, Amblard F, Flint M, Chatterjee P, Kasthuri M, Li C, Russell O, Verma K, Bassit L, Schinazi RF, Nichol ST, Spiropoulou CF (January 2020). "Potent in vitro activity of β-D-4'-chloromethyl-2'-deoxy-2'-fluorocytidine against Nipah virus". Antiviral Research. 175: 104712. doi:10.1016/j.antiviral.2020.104712. PMC 7054849. PMID 31935422.
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