LUMICITABINE

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 Search

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30376079 | https://adisinsight.springer.com/drugs/800038163

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

Title	Date	PubMed
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.	2015 Feb 26	25667954
Respiratory syncytial virus-A dynamics and the effects of lumicitabine, a nucleoside viral replication inhibitor, in experimentally infected humans.	2019 Feb 1	30376079
Advances in respiratory virus therapeutics - A meeting report from the 6th isirv Antiviral Group conference.	2019 Jul	30974127

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 Created by `admin` on `Sat Dec 16 10:28:44 UTC 2023` Edited by `admin` on `Sat Dec 16 10:28:44 UTC 2023`
Record UNII	BNW5PQ52G1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUMICITABINE

Official Name

English

LUMICITABINE [USAN]

Common Name

English

ALS-008176

Code

English

4'-CHLOROMETHYL-2'-DEOXY-3',5'-DI-O-ISOBUTYRYL-2'-FLUOROCYTIDINE

Systematic Name

English

CYTIDINE, 4'-C-(CHLOROMETHYL)-2'-DEOXY-2'-FLUORO-, 3',5'-BIS(2-METHYLPROPANOATE)

Systematic Name

English

ALS-8176

Common Name

English

lumicitabine [INN]

Common Name

English

Lumicitabine [WHO-DD]

Common Name

English

Code System Code Type Description

CAS

1445385-02-3