Synonym
Raluridine; 935U-83; BW-935U-83; FCU; FddClUrd; DRG-0215.
IUPAC/Chemical Name
5-chloro-1-((2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
InChi Key
WKVDSZYIGHLONN-RRKCRQDMSA-N
InChi Code
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
SMILES Code
OC[C@@H]1[C@@H](F)C[C@H](N2C(NC(C(Cl)=C2)=O)=O)O1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
264.64
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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.
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.
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.
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.
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.
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.
