4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydro(2-13C,1,3-15N2)pyrimidin-2-one

• ChemBase ID: 167987
• Molecular Formular: C8H10FN3O3S
• Molecular Mass: 250.22617583
• Monoisotopic Mass: 250.04011504
• SMILES: S1C[C@H](O[C@H]1CO)[15n]1[13c](=O)[15n]c(c(c1)F)N
• Canonical SMILES: Nc1[15n][13c](=O)[15n](cc1F)[C@@H]1CS[C@@H](O1)CO
• InChI: InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1/i8+1,11+1,12+1
• InChIKey: XQSPYNMVSIKCOC-SJLFXUEQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-2-one
• IUPAC Traditional name: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl](2-^1^3C,1,3-^1^5N₂)pyrimidin-2-one
• Synonyms: 4-Amino-5-fluoro-1-[(2R,5S)-2-hydroxymethyl)-1,3-oxathiolan-5-yl]-2-(1H-pyrimidinone-13C,15N2; (-)-2’,3’-Dideoxy-5-fluoro-3’-thiacytidine-13C,15N2; (-)-2'-Deoxy-5-fluoro-3'-thiacytidine-13C,15N2; BW 1592-13C,15N2; BW 524W91-13C,15N2; Coviracil-13C,15N2; Emtriva-13C,15N2; (-)-FTC-13C,15N2; Emtricitabine-13C,15N2

Database IDs

• PubChem SID: 162262119
• PubChem CID: 46781450

CALCULATED PROPERTIES

• Acid pKa: 14.294606
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.8956647
• LogD (pH = 7.4): -0.89566475
• Log P: -0.8956647
• Molar Refractivity: 55.3674 cm^3
• Polarizability: 21.200071 Å^3
• Polar Surface Area: 88.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere -20°C Freezer

DETAILS

Toronto Research Chemicals - E525002

Labelled Emtricitabine. A reverse transcriptase inhibitor. It is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner. A nucleoside analog structurally related to Lamivudine (L172500).

REFERENCES

• Schinazi, R.F., et al.: Antimicrob. Ag. Chemother., 36, 2423 (1992)
• Shockeor, J.P., et al.: Xenobioica, 26, 189 (1992)
• Feng, J.Y., et al.: FASEB J., 13, 1511 (1992)
• Molina, J.-M., et al.: J. Infec. Dis., 182, 599 (2000)