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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H10FN3O3
Molecular Weight 227.1924
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELVUCITABINE

SMILES

NC1=NC(=O)N(C=C1F)[C@H]2O[C@@H](CO)C=C2

InChI

InChIKey=HSBKFSPNDWWPSL-VDTYLAMSSA-N
InChI=1S/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7+/m1/s1

HIDE SMILES / InChI

Molecular Formula C9H10FN3O3
Molecular Weight 227.1924
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Elvucitabine (ACH-126443 or beta-L-Fd4C) is a reverse transcriptase inhibitor exerting antiviral properties. Elvucitabine, an L-cytosine nucleoside analog, is intracellularly phosphorylated to its active 5′-triphosphate metabolite, which has an intracellular half-life of at least 20 hours. Elvucitabine triphosphate inhibits the activity of HIV reverse transcriptase by competing with natural substrates and by causing DNA chain termination after incorporation into viral DNA. Elvucitabine has also demonstrated in vitro and in vivo activity against HBV. Achillion, under license from Vion is developing elvucitabine for the potential treatment of HIV and hepatitis B virus (HBV) infection.

Originator

Approval Year

PubMed

Patents

Substance Class Chemical
Record UNII
M09BUF90C0
Record Status Validated (UNII)
Record Version