ETV

4-AMINO-5-FLUORO-1-[(2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]PYRIMIDIN-2(1H)-ONE

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Chemical Component Summary
Name	4-AMINO-5-FLUORO-1-[(2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]PYRIMIDIN-2(1H)-ONE
Synonyms	5-FLUORO-(-)-L-2',3'-DIDEOXY-3'-THIACYTIDINE; (-)-BETA-2',3'-DIDEOXY-5-FLUORO-3'-THIACYTIDINE; EMTRICITABINE; EMTRIVA
Identifiers	4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
Formula	C₈ H₁₀ F N₃ O₃ S
Molecular Weight	247.247
Type	NON-POLYMER
Isomeric SMILES	C1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F
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

Chemical Details
Formal Charge	0
Atom Count	26
Chiral Atom Count	2
Bond Count	27
Aromatic Bond Count	6

Drug Info: DrugBank

DrugBank ID	DB00879
Name	Emtricitabine
Groups	approved investigational
Description	Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) indicated for the treatment of HIV infection in adults[L9019] or combined with [tenofovir alafenamide] for the prevention of HIV-1 infection in high risk adolescents and adults.[L9010] Emtricitabine is a cytidine analogue.[L9019] The drug works by inhibiting HIV reverse transcriptase, preventing transcription of HIV RNA to DNA.[L9019] Emtricitabine was granted FDA approval on 2 July 2003.[L9019]
Synonyms	5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine Emtricitabine (−)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine (−)-2'-deoxy-5-fluoro-3'-thiacytidine (−)-FTC Emtricitabina (−)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one 4-Amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-1H-pyrimidin-2-one 4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one Emtricitabin (−)-β-2',3'-dideoxy-5-fluoro-3'-thiacytidine Emtricitabinum (2R-cis)-4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinone
Brand Names	Efavirenz/emtricitabine/ Tenofovir Disoproxil Krka Emtricitabine and tenofovir disoproxil fumarate Symtuza Apo-emtricitabine-tenofovir Jamp Emtricitabine/tenofovir Disoproxil Fumarate COMPLERA Access Mylan-emtricitabine/tenofovir Disoproxil Atripla Auro-efavirenz-emtricitabine-tenofovir Sandoz Emtricitabine-tenofovir Emtricitabine/tenofovir Disoproxil Zentiva Emtricitabine/TDF Emtricitabine/teno Fovir Disoproxil Krka D.D. Jamp Efavirenz/emtricitabine/tenofovir Disoproxil Fumarate Mylan-efavirenz/emtricitabine/tenofovir Disoproxil Fumarate Stribild Emtricitabine/ten Ofovir Disoproxil Mylan Biktarvy Mint-emtricitabine/tenofovir Efavirenz, Emtricitabine and Tenofovir Disoproxil Fumarate Descovy Efavirenz/emtricita Bine/tenofovir Disoproxil Mylan Emtricitabine Odefsey Efavirenz, emtricitabine and tenofovir disoproxil fumarate Efavirenz/emtricitabine/ Tenofovir Disoproxil Zentiva Riva-efavirenz/emtricitabine/tenofovir Teva-emtricitabine/tenofovir Stribild Access Emtricitabine/tenofovir Disoproxil Mylan Ag-emtricitabine / Tenofovir Disoproxil Fumarate Truvada Access Apo-efavirenz-emtricitabine-tenofovir Emtricitabine/teno Fovir Disoproxil Krka Truvada PMS-emtricitabine-tenofovir Emtricitabine and Tenofovir Disoproxil Fumarate PMS-efavirenz-emtricitabine-tenofovir Efavirenz, Emtricitabine And Tenofovir Disoproxil Fumarate Genvoya Sandoz Efavirenz/emtricitabine/tenofovir Teva-efavirenz/emtricitabine/tenofovir Emtriva Eviplera Atripla Access Complera Auro-emtricitabine-tenofovir
Indication	Emtricitabine is indicated in combination with other medications for the treatment of HIV-1 infections;[L9019,L9836,L44226] treatment of HIV-1 infections in pediatric patients 25-35kg, treatment of HIV-1 infections in adult patients ≥35kg, for pre exposure prophylaxis of HIV-1 in adolescent and adult patients excluding those who have receptive vaginal sex;[L4388,L9010] treatment of HIV-1 infections in pediatric and adult patients ≥17kg, pre exposure prophylaxis in adolescents and adults ≥35kg;[L9833] treatment of HIV-1 in patients ≥12 years and ≥35kg;[L9587] treatment of HIV-1 in patients weighing ≥35kg;[L9839,L9842] treatment of HIV-1 in patients weighing ≥25kg;[L9647,L9845] and treatment of HIV-1 in patients weighing ≥40kg.[L9848]
Categories	Anti-HIV Agents Anti-Infective Agents Anti-Retroviral Agents Antiinfectives for Systemic Use Antiviral Agents Antivirals for Systemic Use Antivirals used in combination for the treatment of HIV infections Carbohydrates Deoxycytidine Deoxyribonucleosides Dideoxynucleosides Direct Acting Antivirals Enzyme Inhibitors Glycosides Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor MATE 1 Substrates MATE substrates Nucleic Acid Synthesis Inhibitors Nucleic Acids, Nucleotides, and Nucleosides Nucleoside and Nucleotide Reverse Transcriptase Inhibitors Nucleoside Reverse Transcriptase Inhibitors Nucleosides Pyrimidine Nucleosides Pyrimidines Reverse Transcriptase Inhibitors Ribonucleosides
ATC-Code	J05AR19 J05AR08 J05AR17 J05AF09 J05AR09 J05AR20 J05AR06 J05AR03 J05AR22 J05AR18
CAS number	143491-57-0

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Reverse transcriptase/RNaseH	PISPIETVPVKLKPGMDGPKVKQWPLTEEKIKALVEICTEMEKEGKISKI...	unknown	inhibitor
Deoxycytidine kinase	MATPPKRSCPSFSASSEGTRIKKISIEGNIAAGKSTFVNILKQLCEDWEV...	unknown	substrate
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
Multidrug and toxin extrusion protein 1	MEAPEEPAPVRGGPEATLEVRGSRCLRLSAFREELRALLVLAGPAFLVQL...	unknown	substrate

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682