Compounds > als-8176
Page last updated: 2024-11-13

als-8176

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine: an antiviral with RSV polymerase inhibitory activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID89658382
CHEMBL ID3417258
SCHEMBL ID15070623
MeSH IDM000605236

Synonyms (25)

Synonym
SCHEMBL15070623
AC-30919
cytidine, 4'-c-(chloromethyl)-2'-deoxy-2'-fluoro-, 3',5'-bis(2-methylpropanoate)
lumicitabine [inn]
lumicitabine [who-dd]
CHEMBL3417258
lumicitabine [usan]
als-8176
als-008176
bnw5pq52g1 ,
4'-chloromethyl-2'-deoxy-3',5'-di-o-isobutyryl-2'-fluorocytidine
unii-bnw5pq52g1
lumicitabine
1445385-02-3
CS-5699
HY-12983A
A908658
DB14808
[(2r,3r,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(chloromethyl)-4-fluoro-3-(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate
AMY27906
Q27274772
MS-27760
DTXSID801028057
[(2r,3r,4r,5r)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-2-(chloromethyl)-4-fluoro-3-[(2-methylpropanoyl)oxy]oxolan-2-yl]methyl 2-methylpropanoate
EN300-22129548

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" ALS-8176 (71), the 3',5'-di-O-isobutyryl prodrug of 2c, demonstrated good oral bioavailability and a high level of 2c-TP in vivo."( 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.
Beigelman, L; Blatt, LM; Chanda, SM; Deval, J; Dyatkina, N; Fung, A; Hong, J; Jin, Z; Liu, J; Prhavc, M; Serebryany, V; Smith, DB; Stevens, SK; Symons, JA; Tam, Y; Taylor, J; Wang, G; Zhang, Q, 2015)		1.55

Dosage Studied

ExcerptRelevanceReference
" RESULTS A total of 62 participants received placebo or one of three ALS-008176 dosing regimens: 1 loading dose of 750 mg followed by 9 maintenance doses of 500 mg (group 1), 1 loading dose of 750 mg followed by 9 maintenance doses of 150 mg (group 2), or 10 doses of 375 mg (group 3)."( Activity of Oral ALS-008176 in a Respiratory Syncytial Virus Challenge Study.
Beigelman, L; Blatt, LM; Chanda, S; DeVincenzo, JP; Fathi, H; Fry, J; Lambkin-Williams, R; McClure, MW; Smith, P; Symons, JA; Westland, C; Zhang, Q, 2015)		0.42
" Simulated NTP exposures and time to EC50 attainment suggested that rapid therapeutic effects and reduced dosing frequency are achievable in adult and paediatric patients."( Respiratory syncytial virus-A dynamics and the effects of lumicitabine, a nucleoside viral replication inhibitor, in experimentally infected humans.
Beigelman, L; Blatt, LM; Chanda, S; DeVincenzo, JP; Fry, J; Huntjens, DR; Kirkpatrick, CM; McClure, M; Nieforth, KA; Patel, K; Smith, PF; Symons, JA; Zhang, Q, 2019)		0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pathways (6)

PathwayProteinsCompounds
Disease1278231
Infectious disease89579
Viral Infection Pathways72739
Respiratory Syncytial Virus Infection Pathway8915
Respiratory syncytial virus (RSV) genome replication, transcription and translation2513
Respiratory syncytial virus genome transcription38

Bioassays (23)

Assay IDTitleYearJournalArticle
AID1200182Cmax in male syrian golden hamster at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200193Drug uptake in Sprague-Dawley rat assessed as lung NMP level at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose after 1 hr2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200198Half life in Non-naive cynomolgus monkey at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200189Cmax in Sprague-Dawley rat at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200145Drug uptake in Non-naive cynomolgus monkey assessed as lung NTP level at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose after 12 hrs2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200194Drug uptake in Sprague-Dawley rat assessed as lung NTP level at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose after 1 hr2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200143Oral bioavailability in Non-naive cynomolgus monkey at 5 mg/kg 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200185Oral bioavailability in male syrian golden hamster at 5 mg/kg 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200186Drug uptake in male syrian golden hamster assessed as lung NMP level at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose after 1 hr2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200184AUCinf in male syrian golden hamster at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200144Drug uptake in Non-naive cynomolgus monkey assessed as lung NMP level at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose after 12 hrs2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200191AUCinf in Sprague-Dawley rat at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200154Antiviral activity against Respiratory syncytial virus subgenomic replicon system in 395 HeLa cells assessed as reduction in viral replication after 7 days by renilla luciferase assay2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200197Cmax in Non-naive cynomolgus monkey at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200190Half life in Sprague-Dawley rat at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200199AUCinf in Non-naive cynomolgus monkey at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200188Tmax in Sprague-Dawley rat at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200155Cytotoxicity against human HeLa cells assessed as cell viability by CellTiter-Glo luminescent assay2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200192Oral bioavailability in Sprague-Dawley rat at 5 mg/kg 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200183Half life in male syrian golden hamster at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200181Tmax in male syrian golden hamster at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200195Tmax in Non-naive cynomolgus monkey at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
AID1200187Drug uptake in male syrian golden hamster assessed as lung NTP level at 5 mg/kg, po 4'-chloromethyl-2'-deoxy-2'-fluorocytidine equivalent dose after 1 hr2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (85.71)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.39

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.39 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.39)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (28.57%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (57.14%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
deoxycytidine
[no description available]		7.572pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
arabinofuranosylcytosine triphosphate
Arabinofuranosylcytosine Triphosphate: A triphosphate nucleotide analog which is the biologically active form of CYTARABINE. It inhibits nuclear DNA synthesis.		2.1110
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		2.2110benzenes;
phenyl acetates
2',2'-difluorodeoxycytidine 5'-triphosphate
[no description available]		2.1110pyrimidone
4'-azidocytidine
4'-azidocytidine: antiviral; structure in first source		2.1110N-glycosyl compound
ConditionIndicatedRelationship StrengthStudiesTrials
Infections, Respiratory Syncytial Virus
[description not available]		07.1862
Respiratory Syncytial Virus Infections
Pneumovirus infections caused by the RESPIRATORY SYNCYTIAL VIRUSES. Humans and cattle are most affected but infections in goats and sheep have been reported.		19.1862
Ebola Hemorrhagic Fever
[description not available]		03.0410
Rubeola
[description not available]		03.0410
Measles
A highly contagious infectious disease caused by MORBILLIVIRUS, common among children but also seen in the nonimmune of any age, in which the virus enters the respiratory tract via droplet nuclei and multiplies in the epithelial cells, spreading throughout the MONONUCLEAR PHAGOCYTE SYSTEM.		03.0410
Hemorrhagic Fever, Ebola
A highly fatal, acute hemorrhagic fever caused by EBOLAVIRUS.		03.0410