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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

Molecular Formula C9H10ClFN2O4
Molecular Weight 264.638
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
dose range of 100 to 1,500 mg
Route of Administration: Oral
Substance Class Chemical
Record UNII
9D65NWY2K0
Record Status Validated (UNII)
Record Version