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
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
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
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9124852
dose range of 100 to 1,500 mg
Route of Administration:
Oral
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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
|
PRIMARY | |||
|
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 | |||
|
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 | |||
|
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
|
PRIMARY | |||
|
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
|
PRIMARY | |||
|
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
|
PRIMARY | |||
|
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
|
PRIMARY |
SUBSTANCE RECORD