U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H25ClFN3O6
Molecular Weight 433.859
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUMICITABINE

SMILES

CC(C)C(=O)OC[C@@]1(CCl)O[C@H]([C@H](F)[C@@H]1OC(=O)C(C)C)N2C=CC(N)=NC2=O

InChI

InChIKey=MJVKYGMNSQJLIN-KYZVSKTDSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H25ClFN3O6
Molecular Weight 433.859
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Lumicitabine (formerly called ALS-8176), a first-in-class orally administered nucleoside analogue is being developed by Alios BioPharma for the treatment of respiratory syncytial virus infections. Lumicitabine converts to plasma-circulating ALS-8112, and then to the 5'-active nucleoside triphosphate (NTP) form within host cells. Extensive and rapid RSV reduction occurred after lumicitabine treatment (EC50 = 1.79 uM), with >99% viral inhibition at 2 h after loading dose. Clinical trials of Lumicitabine for the treatment of respiratory syncytial virus infection are ongoing.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Respiratory Syncytial Virus Infections: Participants will receive ALS-008176, 250 mg oral suspension once on Day 1 under fasted conditions. Participants will receive ALS-008176, 500 mg oral suspension once on Day 1 under fasted conditions. Participants will receive ALS-008176, 750 mg oral suspension once on Day 1 under fasted conditions.
Route of Administration: Oral
In Vitro Use Guide
ALS-8176 is active in RSV replicon assay with EC50 value 0.26 uM.
Substance Class Chemical
Record UNII
BNW5PQ52G1
Record Status Validated (UNII)
Record Version