Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR5175)
Drug Name
Emtricitabine
Synonyms
Coviracil; DOTFC; Emtriva; RCV; Racivir; BW 1592; BW 524W91; BW524W91; BW-524W91; Coviracil (TN); Coviracil(TM); DRG-0208; Emtriva(TM); Emtricitabine (JAN/USAN/INN); Beta-L-2',3'-dideoxy-5-fluoro-3'-thiacytidine; Beta-L-(-)-(2R,5S)-5-Fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; (-)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine; (-)-.beta.-L-FTC; (-)-2',3'-Dideoxy-5-fluoro-3'-thiacytidine; (-)-2'-Deoxy-5-fluoro-3'-thiacytidine; (-)-FTC; (-)-beta-2',3'-dideoxy-5-fluoro-3'-thiacytidine; (-)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one; (2R-cis)-4-Amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinone; 1-(2-(Hydroxymethyl)oxathiolan-5-yl)-5-fluorocytosine; 2',3',5-FTC; 2',3'-Dideoxy-5-fluoro-3'-thiacytidine; 2'-Deoxy-5-fluoro-3'-oxa-4'-thiocytidine; 2'-Deoxy-5-fluoro-3'-thiacytidine; 2-FTC; 3'-Thia-2'.3'-dideoxy-5-fluorocytidine; 4-Amino-5-fluoro-1-[(2R,5S)-(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; 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one; 5-Fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine; 5-Fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine; 5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)[1,3]oxathiolan-5-yl]cytosine; 524W91; FTC
Indication Hepatitis virus infection [ICD11: 1E50-1E51] Approved [1]
Human immunodeficiency virus infection [ICD11: ICD11: 1C60-1C62] Approved [2]
Hepatitis B virus infection [ICD11: ICD11: 1E50-1E51] Phase 3 [3]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 247.25 Topological Polar Surface Area 113
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
60877
ChEBI ID
CHEBI:31536
CAS Number
143491-57-0
TTD Drug ID
D0S9SD
Formula
C8H10FN3O3S
Canonical 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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Emtricitabine Metabolite M1 DM015303
454858
Unclear - Unclear 1 [4]
Emtricitabine Metabolite M2 DM016487
101697652
Unclear - Unclear 1 [4]
Emtricitabine Metabolite M3 DM018594 N. A. Unclear - Unclear 1 [4]
Emtricitabine Metabolite M4 DM018595 N. A. Unclear - Unclear 1 [4]
Emtricitabine Metabolite M5 DM014861
3366
Unclear - Unclear 1 [4]
Emtricitabine Metabolite M6 DM015304
455170
Unclear - Unclear 1 [4]
Fluorouracil DM000190
3385
Unclear - Unclear 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010700 Emtricitabine Emtricitabine Metabolite M1 Unclear - Unclear Unclear [4]
MR010701 Emtricitabine Emtricitabine Metabolite M2 Unclear - Unclear Unclear [4]
MR010702 Emtricitabine Emtricitabine Metabolite M3 Unclear - Unclear Unclear [4]
MR010703 Emtricitabine Emtricitabine Metabolite M4 Unclear - Unclear Unclear [4]
MR010704 Emtricitabine Emtricitabine Metabolite M5 Unclear - Unclear Unclear [4]
MR010705 Emtricitabine Emtricitabine Metabolite M6 Unclear - Unclear Unclear [4]
MR010706 Emtricitabine Emtricitabine Metabolite M7 Unclear - Unclear Unclear [4]
⏷ Show the Full List of 7 MR(s)
References
1 Nat Rev Drug Discov. 2013 Feb;12(2):87-90.
2 Nat Rev Drug Discov. 2013 Feb;12(2):87-90.
3 Clinical pipeline report, company report or official report of Gilead (2011).
4 Hplc-nmr identification of the human urinary metabolites of (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl] cytosine, a nucleoside analogue active against human immunodeficiency virus (HIV)

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