4-amino-5-fluoro-1-[(2R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

• ChemBase ID: 72788
• Molecular Formular: C8H10FN3O3S
• Molecular Mass: 247.2467032
• Monoisotopic Mass: 247.04269042
• SMILES: n1c(c(cn(c1=O)C1O[C@H](SC1)CO)F)N
• Canonical SMILES: Nc1nc(=O)n(cc1F)C1CS[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-/m1/s1
• InChIKey: XQSPYNMVSIKCOC-PRJDIBJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-fluoro-1-[(2R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 4-amino-5-fluoro-1-[(2R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
• Synonyms: Emtriva; Coviracil; Truvada; Atripla; Emtricitabine

Database IDs

• CAS Number: 143491-57-0
• PubChem SID: 162037709
• PubChem CID: 12043008

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

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: NART

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1704

Research Area: Infection
Biological Activity:
Emtricitabine (Emtriva) is a nucleoside reverse transcriptase inhibitor with an IC50 of 27.7 μM. [1] The drug works by inhibiting reverse transcriptase, the enzyme that copies HIV RNA into new viral DNA. By interfering with this process, which is central to the replication of HIV, emtricitabine can help to lower the amount of HIV, or "viral load", in a patient’s body and can indirectly increase the number of immune system cells (called T cells or CD4+ T-cells). Both of these changes are associated with healthier immune systems and decreased likelihood of serious illness. [2]

REFERENCES

• http://en.wikipedia.org/wiki/Emtricitabine.