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

• ChemBase ID: 757
• Molecular Formular: C8H10FN3O3S
• Molecular Mass: 247.2467032
• Monoisotopic Mass: 247.04269042
• SMILES: S1C[C@H](O[C@H]1CO)n1cc(F)c(nc1=O)N
• Canonical SMILES: Nc1nc(=O)n(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
• InChIKey: XQSPYNMVSIKCOC-NTSWFWBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: emtricitabine
• Brand Name: Coviracil; Emtriva; Racivir
• Synonyms: 4-Amino-5-fluoro-1-[(2R,5S)-2-hydroxymethyl)-1,3-oxathiolan-5-yl]-2-(1H-pyrimidinone; (-)-2’,3’-Dideoxy-5-fluoro-3’-thiacytidine; (-)-2'-Deoxy-5-fluoro-3'-thiacytidine; BW 1592; BW 524W91; Coviracil; Emtriva; (-)-FTC; EMtricitabine; emtricitabine; Emtricitabine; 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one; 恩曲他滨

Database IDs

• CAS Number: 143491-57-0
• MDL Number: MFCD00870151
• PubChem SID: 160964220; 46507606
• PubChem CID: 60877

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.294601
• 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

ALOGPS 2.1

• Log P: -0.8
• LOG S: -2.09
• Solubility (Water): 2.00e+00 g/l

PROPERTIES

Physical Property

• Solubility: 112 mg/mL; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 153-155°C
• Hydrophobicity(logP): -1.291; -1.4

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 95%

DETAILS

DrugBank - DB00879

• Drug Groups: approved; investigational
• Description: Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) for the treatment of HIV infection in adults. Emtricitabine is an analogue of cytidine. The drug works by inhibiting reverse transcriptase, the enzyme that copies HIV RNA into new viral DNA.
• Indication: Indicated, in combination with other antiretroviral agents, for the treatment of HIV-1 infection in adults and for postexposure prophylaxis of HIV infection in health care workers and others exposed occupationally or nonoccupationally via percutaneous injury or mucous membrane or nonintact skin contact with blood, tissues, or other body fluids associated with risk for transmission of the virus.
• Pharmacology: Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Emtricitabine helps to block HIV reverse transcriptase, a chemical in your body (enzyme) that is needed for HIV to multiply. Emtricitabine is always used with other anti-HIV medicines to treat people with HIV infection. Emtricitabine may lower the amount of HIV in the blood (viral load). Emtricitabine may also help to increase the number of T cells called CD4 cells. Lowering the amount of HIV in the blood lowers the chance of death or infections that happen when your immune system is weak (opportunistic infections). People taking emtricitabine may still get opportunistic infections or other conditions that happen with HIV infection.
• Toxicity: Symptoms of overdose include serious liver problems (hepatotoxicity, with liver enlargement and fat in the liver called steatosis) or a lactic acidosis (buildup of an acid in the blood).
• Affected Organisms: Human Immunodeficiency Virus
• Biotransformation: Minimally transformed (13%), most appears unchanged in urine (86%). The biotransformation of emtricitabine includes oxidation of the thiol moiety to form the 3′-sulfoxide diastereomers (~ 9% of dose) and conjugation with glucuronic acid to form 2′-O-glucuronide (~ 4% of dose). In vitro studies indicate emtricitabine is not an inhibitor or cytochrome P450 enzymes.
• Absorption: Rapidly absorbed (mean absolute bioavailability of 93% for capsules, and 75% for solution). Food does not effect absorption.
• Half Life: 10 hours
• Protein Binding: Very low (less than 4%)
• Elimination: The renal clearance of emtricitabine is greater than the estimated creatinine clearance, suggesting elimination by both glomerular filtration and active tubular secretion.
• Clearance: * 302 +/- 94 mL/min [Renal Function Creatinine Clearance>80 ml/min]; * 168 +/- 10 mL/min [Renal Function Creatinine Clearance 50-80 ml/min]; * 138 +/- 28 mL/min [Renal Function Creatinine Clearance 30-49 ml/min]; * 99 +/- 6 mL/min [Renal Function Creatinine Clearance<30 ml/min]; * 64 +/- 12 mL/min [ESRD patients requiring dialysis]
• References: Masho SW, Wang CL, Nixon DE: Review of tenofovir-emtricitabine. Ther Clin Risk Manag. 2007 Dec;3(6):1097-104. [Pubmed] ; Long MC, King JR, Acosta EP: Pharmacologic aspects of new antiretroviral drugs. Curr HIV/AIDS Rep. 2009 Feb;6(1):43-50. [Pubmed] ; Emtricitabine/tenofovir disoproxil fumarate. Drugs R D. 2004;5(3):160-1. [Pubmed] ; Goicoechea M, Best B: Efavirenz/emtricitabine/tenofovir disoproxil fumarate fixed-dose combination: first-line therapy for all? Expert Opin Pharmacother. 2007 Feb;8(3):371-82. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - E525000

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

• Emtricitabine/tenofovir disoproxil fumarate. Drugs R D. 2004;5(3):160-1. Pubmed
• Masho SW, Wang CL, Nixon DE: Review of tenofovir-emtricitabine. Ther Clin Risk Manag. 2007 Dec;3(6):1097-104. Pubmed
• Long MC, King JR, Acosta EP: Pharmacologic aspects of new antiretroviral drugs. Curr HIV/AIDS Rep. 2009 Feb;6(1):43-50. Pubmed
• Goicoechea M, Best B: Efavirenz/emtricitabine/tenofovir disoproxil fumarate fixed-dose combination: first-line therapy for all? Expert Opin Pharmacother. 2007 Feb;8(3):371-82. Pubmed
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