Compounds > raluridine
Page last updated: 2024-11-08

raluridine

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

Description

raluridine: inhibitor of HIV; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID451480
CHEMBL ID2106991
SCHEMBL ID419653
MeSH IDM0165994

Synonyms (34)

Synonym
935u-83
raluridine (usan)
D05695
bw 935u83
5clu:
5-chloro-1-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
2',3'-dideoxy-3'-fluoro-5-chlorouridine
119644-22-3
raluridine
fddclu
5-chloro-1-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
5-chloro-2',3'-dideoxy-3'-fluoro-uridine
935-u-83
CHEMBL2106991
3'-fluoro-2',3'-dideoxy-5-chlorouridine
fddciu
935u83
5-chloro-2',3'-dideoxy-3'-fluorouridine
unii-9d65nwy2k0
fddclurd
9d65nwy2k0 ,
uridine, 5-chloro-2',3'-dideoxy-3'-fluoro-
drg-0215
raluridine [usan]
SCHEMBL419653
raluridine [who-dd]
AC-32302
DTXSID30152541
AKOS030568062
DB12894
5-chloro-1-((2r,4s,5r)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
WKVDSZYIGHLONN-RRKCRQDMSA-N
5-chloro-3'-fluoro-2',3'-dideoxyuridine
Q27272384

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In the dose range of 100 to 1,500 mg 935U83 was well tolerated by all subjects with no drug-related adverse events reported."( Safety and pharmacokinetics of 5-chloro-2',3'-dideoxy-3'-fluorouridine (935U83) following oral administration of escalating single doses in human immunodeficiency virus-infected adults.
Bartlett, JA; Blum, MR; Dunn, JA; Elkins, MM; McMahon, DK; Mellors, JW; Packard, MV; Riddler, SA; Savina, PM; Wang, LH, 1996)		0.29

Bioavailability

ExcerptReferenceRelevance
" Pharmacokinetic evaluation showed good oral bioavailability (86% in mice and 60% in monkeys) and less extensive metabolism to the glucuronide relative to AZT."( 5-Chloro-2',3'-dideoxy-3'-fluorouridine (935U83), a selective anti-human immunodeficiency virus agent with an improved metabolic and toxicological profile.
Ayers, KM; Daluge, SM; Dev, IK; Novak, P; Parry, NR; Purifoy, DJ; Reardon, JE; Roberts, GB; Savina, PM; St Clair, MH, 1994)		0.29
" The effect of a high-fat meal on the oral bioavailability of 935U83 was also assessed."( Safety and pharmacokinetics of 5-chloro-2',3'-dideoxy-3'-fluorouridine (935U83) following oral administration of escalating single doses in human immunodeficiency virus-infected adults.
Bartlett, JA; Blum, MR; Dunn, JA; Elkins, MM; McMahon, DK; Mellors, JW; Packard, MV; Riddler, SA; Savina, PM; Wang, LH, 1996)		0.29

Dosage Studied

ExcerptRelevanceReference
" Mild reversible reductions in erythrocytes and associated parameters were seen in mice dosed orally with 2,000 mg of 935U83 per kg per day for 1 and 6 months."( 5-Chloro-2',3'-dideoxy-3'-fluorouridine (935U83), a selective anti-human immunodeficiency virus agent with an improved metabolic and toxicological profile.
Ayers, KM; Daluge, SM; Dev, IK; Novak, P; Parry, NR; Purifoy, DJ; Reardon, JE; Roberts, GB; Savina, PM; St Clair, MH, 1994)		0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1ED500.38000.00020.99359.8000AID105582
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID235486Selectivity index is the ratio of ED50 and CD50 values against inhibition of HIV-1 in MT-4 cells1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
3'-Fluoro-2',3'-dideoxy-5-chlorouridine: most selective anti-HIV-1 agent among a series of new 2'- and 3'-fluorinated 2',3'-dideoxynucleoside analogues.
AID1652588Cytotoxicity in human CEM/0 cells assessed as reduction in cell viability incubated for 4 to 5 days
AID104310Effective dose achieving 50% protection of MT-4 cells against the cytopathic effect of HIV1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.
AID1652587Antiviral activity against HIV2 ROD infected in human TK-deficient CEM/TK(-) cells assessed as inhibition of viral-induced giant cell formation incubated for 4 to 5 days by microscopy
AID235704Selectivity index of CD50 to ED50 of MT-4 cells1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.
AID105582Inhibitory activity against HIV-1 replication in MT-4 cells1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
3'-Fluoro-2',3'-dideoxy-5-chlorouridine: most selective anti-HIV-1 agent among a series of new 2'- and 3'-fluorinated 2',3'-dideoxynucleoside analogues.
AID106768Cytotoxic dose required to reduce the viability of normal uninfected MT-4 cells by 50%1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.
AID1652585Antiviral activity against HIV1 3B infected in human CEM/0 cells assessed as inhibition of viral-induced giant cell formation incubated for 4 to 5 days by microscopy
AID105376Cytotoxic dose in MT-4 cells1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
3'-Fluoro-2',3'-dideoxy-5-chlorouridine: most selective anti-HIV-1 agent among a series of new 2'- and 3'-fluorinated 2',3'-dideoxynucleoside analogues.
AID1652586Antiviral activity against HIV2 ROD infected in human CEM/0 cells assessed as inhibition of viral-induced giant cell formation incubated for 4 to 5 days by microscopy
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (25.00)18.7374
1990's5 (62.50)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.39

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.39 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.69 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.39)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (12.50%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
thymidine
[no description available]		1.9710pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
uridine
[no description available]		1.9710uridinesdrug metabolite;
fundamental metabolite;
human metabolite
deoxycytidine
[no description available]		1.9710pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
stavudine
Stavudine: A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.. stavudine : A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase		1.9710dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
dideoxyadenosine
Dideoxyadenosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.		1.9710adenosines;
purine 2',3'-dideoxyribonucleoside		EC 3.5.4.4 (adenosine deaminase) inhibitor;
EC 4.6.1.1 (adenylate cyclase) inhibitor
zalcitabine
Zalcitabine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.. zalcitabine : A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.		1.9710pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		1.9910delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
alovudine
[no description available]		2.3820pyrimidine 2',3'-dideoxyribonucleoside
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		2.6730azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxyuridine
[no description available]		1.9710
2',3'-dideoxycytidinene
2',3'-dideoxycytidinene: 2',3'-unsaturated derivative of 2',3'-dideoxycytidine; potent inhibitor of HTLV-III in vitro; structure given in first source		1.9710
1-(2,3-dideoxy-2-fluoropentofuranosyl)cytosine
[no description available]		1.9710
2',3'-didehydro-2',3'-dideoxyuridine
[no description available]		1.9710
3'-fluoro-2',3'-dideoxyuridine
[no description available]		2.3820
3'-azido-2',3'-dideoxyadenosine
[no description available]		1.9710
3'-azido-2',3'-dideoxycytidine
[no description available]		1.9710
ConditionIndicatedRelationship StrengthStudiesTrials
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		02.3820
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		01.9910
HIV Coinfection
[description not available]		03.3711
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		15.3711
Cell Transformation, Viral
An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.		01.9710