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143491-57-0 , Emtricitabine, CAS:143491-57-0

143491-57-0 , Emtricitabine,
CAS:143491-57-0
C8H10FN3O3S / 247.25
MFCD00870151

Emtricitabine , 恩曲他滨

Emtricitabine is a synthetic fluoro derivative of thiacytidine with potent antiviral activity. Emtricitabine is phosphorylated to form emtricitabine 5'-triphosphate within the cell. This metabolite inhibits the activity of human immunodeficiency virus (HIV) reverse transcriptase both by competing with the natural substrate deoxycytidine 5'-triphosphate and by incorporation into viral DNA causing a termination of DNA chain elongation (due to the lack of the essential 3'-OH group).

Emtricitabine is a nucleoside analogue and reverse transcriptase inhibitor used in combination with other agents for treatment and prevention of human immunodeficiency virus (HIV) infection and the acquired immunodeficiency syndrome (AIDS). Emtricitabine does not appear to be a significant cause of drug induced liver injury, but may cause flares of disease in patients with underlying chronic hepatitis B virus (HBV) infection.

Emtricitabine, also known as emtriva or 524W91, belongs to the class of organic compounds known as 3'-thia pyrimidine nucleosides. These are nucleoside analogues with a structure that consists of a pyrimidine base, which is N-substituted at the 1-position with a 3'-thia derivative (1, 3-oxazolidine) of the ribose moiety that is characteristic of nucleosides. Emtricitabine exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). Emtricitabine has been detected in multiple biofluids, such as urine and blood. Within the cell, emtricitabine is primarily located in the cytoplasm. In humans, emtricitabine is involved in the emtricitabine action pathway.

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.

CAS Number143491-57-0
Product NameEmtricitabine
IUPAC Name4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
Molecular FormulaC8H10FN3O3S
Molecular Weight247.25 g/mol
InChIInChI=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
InChI KeyXQSPYNMVSIKCOC-RITPCOANSA-N
SMILESC1C(OC(S1)CO)N2C=C(C(=NC2=O)N)F
Solubility112 mg/mL
About 1.12X10+6 mg/L in water at 25 °C
2.00e+00 g/L
Synonyms1-(2-(hydroxymethyl)oxathiolan-5-yl)-5-fluorocytosine, 2',3',5-FTC, 2',3'-dideoxy-5-fluoro-3'-thiacytidine, 2',3'-dideoxy-5-fluoro-3'-thiacytidine, (2S-cis)-isomer, 5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine, 524W91, BW 524W91, BW-524W91, BW524W91, Racivir
Canonical SMILESC1C(OC(S1)CO)N2C=C(C(=NC2=O)N)F
Isomeric SMILESC1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F


CAS No: 143491-57-0,143491-54-7 Synonyms: Emtricitabine(-)-2',3'-Dideoxy-5-fluoro-3'-thiacytidine(-)-cis-FTC4-Amino-5-fluoro-1-[(2R,5S)-2-hydroxymethyl)-1,3-oxathiolan-5-yl]-2-(1H-pyrimidinoneEmtriva MDL No: MFCD00870151 Chemical Formula: C8H10FN3O3S Molecular Weight: 247.25

COA:

Name: Emtricitabine 

CAS143491-57-0     M.F.C8H10FN3O3S       M.W.247.25

Items

Standards

Results

Appearance

White crystalline powder

Positive

Solubility

Freely soluble in CH3OH and H2O; Practically insoluble in CH2Cl2

Complies

NMR and MS

Should comply

Complies

Identification

IR and HPLC

Positive

Specific rotation

-105o ~ -115o

-107.5o

Alpha-Isomer

Max. 0.3%

0

Water

Max. 0.5%

Max. 0.1%

Heavy metal

Max. 20ppm

Complies

Residue On Ignition

Max. 0.1

0.02%

Any impurity

Max. 0.5%

Complies

Purity by HPLC

Max. 98%

99.8%

Assay

98% ~ 102%

99.6%


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