Raluridine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 406848

CAS#: 119644-22-3

Description: 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.


Price and Availability

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Raluridine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 406848
Name: Raluridine
CAS#: 119644-22-3
Chemical Formula: C9H10ClFN2O4
Exact Mass: 264.0313
Molecular Weight: 264.6374
Elemental Analysis: C, 40.85; H, 3.81; Cl, 13.40; F, 7.18; N, 10.59; O, 24.18


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


Technical Data

Appearance:
Solid powder

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).

Harmonized System Code:
293490


References

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.