For research use only. Not for therapeutic Use.
Raluridine, also known as 935U-83; DRG-0215; BW-935U-83; FCU; FddClUrd, is a RNA-directed DNA polymerase inhibitor potentially for the treatment of HIV infection. 935U83 inhibited virus growth with an average 50% inhibitory concentration (IC50) of 1.8 microM; corresponding IC50s were 0.10 microM for FLT (3/’-deoxy-3/’-fluorothymidine) and 0.23, 0.49, and 0.03 microM for the approved agents AZT, ddI (2/’,3/’-dideoxyinosine), and ddC (2/’,3/’-dideoxycytosine), respectively.
| Catalog Number | R026931 |
| CAS Number | 119644-22-3 |
| Synonyms | 2’,3’-Dideoxy-3’-fluoro-5-chlorouridine; 5-Chloro-3’-fluoro-2’,3’-dideoxyuridine; 935U83; BW 935U83; GW 274666X |
| Molecular Formula | C9H10ClFN2O4 |
| Purity | ≥95% |
| Target | Nucleoside Antimetabolite/Analog |
| Storage | Store at RT |
| IUPAC Name | 5-chloro-1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione |
| InChI | 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 |
| InChIKey | WKVDSZYIGHLONN-RRKCRQDMSA-N |
| SMILES | C1C(C(OC1N2C=C(C(=O)NC2=O)Cl)CO)F |
| Reference | </br> 1: Riddler SA, Wang LH, Bartlett JA, Savina PM, Packard MV, McMahon DK, Blum MR, Dunn JA, Elkins MM, Mellors JW. 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. Antimicrob Agents Chemother. 1996 Dec;40(12):2842-7. PubMed PMID: 9124852; PubMed Central PMCID: PMC163633.</br>2: Dunn JA, Savina PM. Validation of a high-performance liquid chromatographic-mass spectrometric method for the measurement of 5-chloro-2/’,3/’-dideoxy-3/’ -fluorouridine (935U83) in human plasma. J Chromatogr B Biomed Appl. 1996 Nov 15;686(2):241-8. PubMed PMID: 8971606.</br>3: Sundseth R, Joyner SS, Moore JT, Dornsife RE, Dev IK. The anti-human immunodeficiency virus agent 3/’-fluorothymidine induces DNA damage and apoptosis in human lymphoblastoid cells. Antimicrob Agents Chemother. 1996 Feb;40(2):331-5. PubMed PMID: 8834875; PubMed Central PMCID: PMC163111.</br>4: Daluge SM, Purifoy DJ, Savina PM, St Clair MH, Parry NR, Dev IK, Novak P, Ayers KM, Reardon JE, Roberts GB, et al. 5-Chloro-2/’,3/’-dideoxy-3/’-fluorouridine (935U83), a selective anti-human immunodeficiency virus agent with an improved metabolic and toxicological profile. Antimicrob Agents Chemother. 1994 Jul;38(7):1590-603. PubMed PMID: 7526782; PubMed Central PMCID: PMC284598.</br>5: Van Aerschot A, Herdewijn P, Balzarini J, Pauwels R, De Clercq E. 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. J Med Chem. 1989 Aug;32(8):1743-9. PubMed PMID: 2754700.</br>6: Balzarini J, Van Aerschot A, Pauwels R, Baba M, Schols D, Herdewijn P, De Clercq E. 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. Mol Pharmacol. 1989 May;35(5):571-7. PubMed PMID: 2725468.</br></br></br> |
