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

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H10ClFN2O4
Molecular Weight 264.638
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RALURIDINE

SMILES

OC[C@H]1O[C@H](C[C@@H]1F)N2C=C(Cl)C(=O)NC2=O

InChI

InChIKey=WKVDSZYIGHLONN-RRKCRQDMSA-N
InChI=1S/C9H10ClFN2O4/c10-4-2-13(9(16)12-8(4)15)7-1-5(11)6(3-14)17-7/h2,5-7,14H,1,3H2,(H,12,15,16)/t5-,6+,7+/m0/s1

HIDE SMILES / InChI
Raluridine (also know as 935U83) is a nucleoside analog reverse transcriptase inhibitor patented by Wellcome Foundation Ltd. for the treatment of HIV infection. Raluridine has demonstrated selective anti-human immunodeficiency virus (HIV) activity in vitro and favorable safety profiles in monkeys and mice. When tested in phytohemagglutinin-stimulated normal human peripheral blood lymphocytes against fresh clinical isolates of HIV type 1 Raluridine inhibited virus growth with an average 50% inhibitory concentration of 1.8 microM. Importantly, Raluridine retained activity against HIV strains that were resistant to zidovudine, 2',3'-dideoxyinosine, or 2',3'-dideoxycytosine. The anabolic profile of Raluridine was similar to that of zidovudine, and Raluridine triphosphate was a potent inhibitor of HIV-1 reverse transcriptase. In clinical trials systemic exposure to Raluridine at levels exceeding its average in vitro antiretroviral 50%, inhibitory concentration (approximately 1.8 microM) can be achieved after a single oral dose.

Approval Year

PubMed

PubMed

TitleDatePubMed
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.
1989 Aug
5-Chloro-substituted derivatives of 2', 3'-didehydro-2',3'-dideoxyuridine, 3'-fluoro-2',3'-dideoxyuridine and 3'-azido-2',3'-dideoxyuridine as anti-HIV agents.
1989 Mar 15
5-Halogeno-3'-fluoro-2',3'-dideoxyuridines as inhibitors of human immunodeficiency virus (HIV): potent and selective anti-HIV activity of 3'-fluoro-2',3'-dideoxy-5-chlorouridine.
1989 May
Inhibition of HIV-replication by 3'-fluoro-modified nucleosides with low cytotoxicity.
1989 Nov 30
Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication.
1992 Jul 1
5-Chloro-2',3'-dideoxy-3'-fluorouridine (935U83), a selective anti-human immunodeficiency virus agent with an improved metabolic and toxicological profile.
1994 Jul
Synthesis and antiviral evaluation of some beta-L-2', 3'-dideoxy-5-chloropyrimidine nucleosides and pronucleotides.
2000 Mar
Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides.
2005 Dec 15
Patents

Sample Use Guides

dose range of 100 to 1,500 mg
Route of Administration: Oral
Name Type Language
RALURIDINE
USAN   WHO-DD  
USAN  
Official Name English
935-U-83
Code English
RALURIDINE [USAN]
Common Name English
Raluridine [WHO-DD]
Common Name English
935U83
Code English
5-CHLORO-2',3'-DIDEOXY-3'-FLUOROURIDINE
Systematic Name English
URIDINE, 5-CHLORO-2',3'-DIDEOXY-3'-FLUORO-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1557
Created by admin on Fri Dec 15 17:45:23 GMT 2023 , Edited by admin on Fri Dec 15 17:45:23 GMT 2023
Code System Code Type Description
PUBCHEM
451480
Created by admin on Fri Dec 15 17:45:23 GMT 2023 , Edited by admin on Fri Dec 15 17:45:23 GMT 2023
PRIMARY
FDA UNII
9D65NWY2K0
Created by admin on Fri Dec 15 17:45:23 GMT 2023 , Edited by admin on Fri Dec 15 17:45:23 GMT 2023
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ChEMBL
CHEMBL2106991
Created by admin on Fri Dec 15 17:45:23 GMT 2023 , Edited by admin on Fri Dec 15 17:45:23 GMT 2023
PRIMARY
CAS
119644-22-3
Created by admin on Fri Dec 15 17:45:23 GMT 2023 , Edited by admin on Fri Dec 15 17:45:23 GMT 2023
PRIMARY
USAN
HH-69
Created by admin on Fri Dec 15 17:45:23 GMT 2023 , Edited by admin on Fri Dec 15 17:45:23 GMT 2023
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NCI_THESAURUS
C152150
Created by admin on Fri Dec 15 17:45:23 GMT 2023 , Edited by admin on Fri Dec 15 17:45:23 GMT 2023
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DRUG BANK
DB12894
Created by admin on Fri Dec 15 17:45:23 GMT 2023 , Edited by admin on Fri Dec 15 17:45:23 GMT 2023
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EPA CompTox
DTXSID30152541
Created by admin on Fri Dec 15 17:45:23 GMT 2023 , Edited by admin on Fri Dec 15 17:45:23 GMT 2023
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