Emtricitabine

Title: Emtricitabine
CAS Registry Number: 143491-57-0
CAS Name: 4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone
Additional Names: (-)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one; (-)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; (-)-b-2¢,3¢-dideoxy-5-fluoro-3¢-thiacytidine; (-)-FTC
Manufacturers' Codes: 524W91; BW-524W91
Trademarks: Coviracil (Triangle); Emtriva (Gilead)
Molecular Formula: C8H10FN3O3S
Molecular Weight: 247.25
Percent Composition: C 38.86%, H 4.08%, F 7.68%, N 16.99%, O 19.41%, S 12.97%
Literature References: Reverse transcriptase inhibitor; nucleoside analog structurally related to lamivudine, q.v. Prepn: D. C. Liotta et al., WO 9214743 (1992 to Emory University); G. Dionne, US 5538975 (1996 to BioChem Pharma, Inc.); L. S. Jeong et al., J. Med. Chem. 36, 181 (1993). Absolute configuration: P. van Roey et al., Antiviral Chem. Chemother. 4, 369 (1993). HPLC-NMR determn of urinary metabolites: J. P. Shockcor et al., Xenobiotica 26, 189 (1996). Comparative efficacy of enantiomers vs HIV: R. F. Schinazi et al., Antimicrob. Agents Chemother. 36, 2423 (1992). Pharmacokinetics: L. W. Frick et al., ibid. 38, 2722 (1994). Mechanism of action study: J. Y. Feng et al., FASEB J. 13, 1511 (1999). Clinical study in combination with didanosine and efavirenz: J.-M. Molina et al., J. Infect. Dis. 182, 599 (2000). Review: P. Cahn, Expert Opin. Invest. Drugs 13, 55-68 (2004).
Properties: White solid from ether and methanol, mp 136-140°. [a]D25 -133.60° (c = 0.23 in MeOH). uv max (water): 287.8 nm (pH 2); 280.0 nm (pH 7); 279.8 nm (pH 11) (e 14210, 11090, 11810).
Melting point: mp 136-140°
Optical Rotation: [a]D25 -133.60° (c = 0.23 in MeOH)
Absorption maximum: uv max (water): 287.8 nm (pH 2); 280.0 nm (pH 7); 279.8 nm (pH 11) (e 14210, 11090, 11810)
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones; Reverse Transcriptase Inhibitor.
Enalapril Enalaprilat Enallylpropymal Enanthotoxin Encainide

Emtricitabine
Emtricitabine-skeletal.svg
Systematic (IUPAC) name
4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
Clinical data
Trade names Emtriva
AHFS/Drugs.com monograph
MedlinePlus a604004
Pregnancy cat. B1 (AU) B (US)
Legal status POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 93%
Protein binding Very low (less than 4%)
Metabolism Hepatic oxidation and glucuronidation
CYP system not involved
Half-life 10 hours
Excretion Renal (86%) and fecal (14%)
Identifiers
CAS number 143491-57-0 YesY
ATC code J05AF09
PubChem CID 60877
DrugBank DB00879
ChemSpider 54859 YesY
UNII G70B4ETF4S YesY
KEGG D01199 YesY
ChEBI CHEBI:31536 YesY
ChEMBL CHEMBL885 YesY
NIAID ChemDB 004782
Chemical data
Formula C8H10FN3O3S 
Mol. mass 247.248 g/mol
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Emtricitabine (FTC), with trade name Emtriva (formerly Coviracil), is a nucleoside reverse transcriptase inhibitor (NRTI) for the treatment of HIV infection in adults and children.

Emtricitabine is also marketed in a fixed-dose combination with tenofovir (Viread) under the brand name Truvada. A fixed-dose triple combination of emtricitabine, tenofovir and efavirenz (Sustiva, marketed by Bristol-Myers Squibb) was approved by the U.S. Food and Drug Administration (FDA) on July 12, 2006 under the brand name Atripla.

Emtricitabine makes up one fourth of the Quad pill (brand name: Stribild).