Drug Information

Drug (ID: DG00939) and It's Reported Resistant Information

• Name: Emtricitabine
• Synonyms: Emtricitabine; 143491-57-0; Emtriva; Coviracil; (-)-FTC; 4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one; 143491-54-7; 524W91; BW-524W91; Racivir; 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one; BW524W91; (-)-2'-Deoxy-5-fluoro-3'-thiacytidine; UNII-G70B4ETF4S; BW 524W91; FTC; (-)-beta-2',3'-dideoxy-5-fluoro-3'-thiacytidine; CHEBI:31536; FTC-(-); (2R-cis)-4-Amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinone; 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one; 5-Fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine; G70B4ETF4S; 145213-48-5; Emtritabine; BW1592; MFCD00870151; (-)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one; 2',3'-Dideoxy-5-fluoro-3'-thiacytidine; NCGC00164564-01; (-)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; PSI 5004; PSI-5004; Coviracil(TM); DRG-0208; 4-Amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-1H-pyrimidin-2-one; rel-4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; Emtriva(TM); 2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, rel-; 2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, rel-; Emtricitabine (Emtriva); SMR002533604; BW 1592; 2',3',5-FTC; HSDB 7337; 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one; FTC, (-)-; Emtricitabine [USAN:INN]; (-)-.beta.-L-FTC; Emtricitabinum; 2(1h)-pyrimidinone,4-amino-5-fluoro-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-; 2(1H)-Pyrimidinone,4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-; (-)-emtricitabine; Emtricitabine- Bio-X; Emtricitabine, (-)-; CHEMBL885; 2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, cis-; DSSTox_CID_20129; DSSTox_RID_79445; DSSTox_GSID_40129; SCHEMBL39708; MLS003882429; MLS006011556; MLS006011987; DTXSID0040129; GTPL11244; EX-A150; HMS2089I05; HMS3713L12; ZINC3629271; Tox21_112193; ((-))-FTC; BDBM50107843; CS1125; FTC-((-)); NSC804863; s1704; AKOS015853098; AKOS015894950; AM84393; CCG-220615; CS-1370; DB00879; MCULE-7141046266; NSC-804863; 2',3'-Dideoxy-3-thia-5-fluorocytidine; NCGC00164564-06; NCGC00164564-09; NCGC00164564-10; 2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2R-cis)-; 2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, cis-(+-)-; AS-14099; BE165946; HY-17427; CAS-143491-57-0; E1007; Emtricitabine 100 microg/mL in Acetonitrile; SW220172-1; D01199; D72669; ent-Emtricitabine; Emtricitabine IP Impurity D; AB01275429-01; 491E570; Q422604; 524-W-91; W-201247; W-201248; Z1739256297; UNII-ULS8902U4O component XQSPYNMVSIKCOC-NTSWFWBYSA-N; .beta.-L-(-)-(2R,5S)-5-Fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; 4-Amino-5-fluoro-1-[(2R,5S)-2-hydroxymethyl)-1,3-oxathiolan-5-yl]-2-(1H-pyrimidinone; 4-Amino-5-fluoro-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; (+)-2'-Deoxy-3'-thia-5-fluorocytidine; (2S-cis)-4-Amino-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; 5-FLUORO-(-)-L-2',3'-DIDEOXY-3'-THIACYTIDINE; (-)-BETA-2',3'-DIDEOXY-5-FLUORO-3'-THIACYTIDINE; EMTRICITABINE; EMTRIVA
• Indication:
  In total 3 Indication(s)
  Hepatitis B virus infection [ICD-11: 1E50-1E51]; Approved; [1]
  Hepatitis virus infection [ICD-11: 1E50-1E51]; Approved; [1]
  Human immunodeficiency virus infection [ICD-11: 1C60-1C62]; Approved; [1]
• Drug Resistance Disease(s):
  Disease(s) with Resistance Information Validated by in-vivo Model for This Drug (1 diseases)
  HIV infection [ICD-11: 1C62]; [1]
• Target: Human immunodeficiency virus Reverse transcriptase (HIV RT); POL_HV1B1; [1]
• Formula: C8H10FN3O3S
• IsoSMILES: C1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F
• 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
• PubChem CID: 60877
• ChEBI ID: CHEBI:31536
• TTD Drug ID: D0S9SD
• VARIDT ID: DR00672
• DrugBank ID: DB00879

Type(s) of Resistant Mechanism of This Drug

  ADTT: Aberration of the Drug's Therapeutic Target

Drug Resistance Data Categorized by Their Corresponding Diseases

ICD-01: Infectious/parasitic diseases

HIV infection [ICD-11: 1C62]

Drug Resistance Data Categorized by Their Corresponding Mechanisms

Aberration of the Drug's Therapeutic Target (ADTT)

Key Molecule: Gag-Pol polyprotein (POL) [1]

• Molecule Alteration: Missense mutation+Missense mutation; p.M184V+p.M184I
• Resistant Disease: Human immunodeficiency virus infection [ICD-11: 1C62.0]
• Experimental Note: Discovered Using In-vivo Testing Model
• Mechanism Description: Certain amino acid substitutions in the reverse transcriptase of HIV-1 can also reduce susceptibility to emtricitabine (M184V/I) and tenofovir AF (K65R, sometimes plus S68N or L429I; and transiently K70E), although selection of high-level resistance has not occurred with the latter drug over extended periods of culture in vitro.

References

• Ref 1: Resistance Analysis of Bictegravir-Emtricitabine-Tenofovir Alafenamide in HIV-1 Treatment-Naive Patients through 48 Weeks .Antimicrob Agents Chemother. 2019 Apr 25;63(5):e02533-18. doi: 10.1128/AAC.02533-18. Print 2019 May. 10.1128/AAC.02533-18