Details of the Drug

General Information of Drug (ID: DMBMUWZ)

• 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

Disease Entry	ICD 11	Status	REF
Hepatitis virus infection	1E50-1E51	Approved	[1]
Human immunodeficiency virus infection	1C62	Approved	[1]
Hepatitis B virus infection	1E51.0	Phase 3	[2]

• Therapeutic Class: Anti-HIV Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 247.25
  Logarithm of the Partition Coefficient (xlogp); -0.6
  Rotatable Bond Count (rotbonds); 2
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 5
• ADMET Property:
  Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 10 +/- 3.1 mgh/L [3]
  Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 1.8 +/- 0.7 mg/L [3]
  Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1-2 h [3]
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
  Clearance: The clearance of drug is 15.1 L/h [5]
  Elimination: Emtricitabine is 86% recovered in the urine and 14% recovered in feces [3]
  Half-life: The concentration or amount of drug in body reduced by one-half in 10 hours [3]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 11.5557 micromolar/kg/day [6]
  Vd: The volume of distribution (Vd) of drug is 55.4 L [5]
  Water Solubility: The ability of drug to dissolve in water is measured as 112 mg/mL [4]
• Chemical Identifiers:
  Formula: C8H10FN3O3S
  IUPAC Name: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
  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
• Cross-matching ID:
  PubChem CID: 60877
  ChEBI ID: CHEBI:31536
  CAS Number: 143491-57-0
  DrugBank ID: DB00879
  TTD ID: D0S9SD
  VARIDT ID: DR00672
  ACDINA ID: D00228
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Human immunodeficiency virus Reverse transcriptase (HIV RT)	TT84ETX	POL_HV1B1	Modulator	[1]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Multidrug and toxin extrusion protein 1 (SLC47A1)	DTZGT0P	S47A1_HUMAN	Substrate	[7]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Albumin (ALB)	OTVMM513	ALBU_HUMAN	Protein Interaction/Cellular Processes	[8]
Deoxycytidine kinase (DCK)	OTW8HLZC	DCK_HUMAN	Protein Interaction/Cellular Processes	[9]
E3 ubiquitin-protein ligase parkin (PRKN)	OTJBN41W	PRKN_HUMAN	Gene/Protein Processing	[10]

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Emtricitabine

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Emtricitabine caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[11]

Coadministration of a Drug Treating the Disease Different from Emtricitabine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Emtricitabine and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[11]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Emtricitabine and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[12]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Emtricitabine and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[13]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Emtricitabine and Cannabidiol.	Epileptic encephalopathy [8A62]	[14]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Emtricitabine and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[15]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Emtricitabine and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[16]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Emtricitabine and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[17]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Emtricitabine and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[18]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Emtricitabine and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[19]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Emtricitabine and Idelalisib.	Mature B-cell leukaemia [2A82]	[20]
Orlistat	DMRJSP8	Moderate	Altered absorption of Emtricitabine caused by Orlistat.	Obesity [5B80-5B81]	[21]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Emtricitabine and Leflunomide.	Rheumatoid arthritis [FA20]	[17]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Emtricitabine and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[14]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
FD&C blue no. 2	E00446	2723854	Colorant
Crospovidone	E00626	Not Available	Disintegrant
Magnesium stearate	E00208	11177	lubricant
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Emtricitabine 200 mg capsule	200 mg	Oral Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] Nat Rev Drug Discov. 2013 Feb;12(2):87-90.
• [2] Clinical pipeline report, company report or official report of Gilead (2011).
• [3] FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules
• [4] BDDCS applied to over 900 drugs
• [5] Valade E, Treluyer JM, Bouazza N, Ghosn J, Foissac F, Benaboud S, Fauchet F, Viard JP, Urien S, Hirt D: Population pharmacokinetics of emtricitabine in HIV-1-infected adult patients. Antimicrob Agents Chemother. 2014;58(4):2256-61. doi: 10.1128/AAC.02058-13. Epub 2014 Feb 3.
• [6] Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
• [7] Emtricitabine is a substrate of MATE1 but not of OCT1, OCT2, P-gp, BCRP or MRP2 transporters. Xenobiotica. 2017 Jan;47(1):77-85.
• [8] Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. doi: 10.1080/15216540400016286.
• [9] Nonenantioselectivity property of human deoxycytidine kinase explained by structures of the enzyme in complex with L- and D-nucleosides. J Med Chem. 2007 Jun 28;50(13):3004-14. doi: 10.1021/jm0700215. Epub 2007 May 27.
• [10] Chronic Nucleoside Reverse Transcriptase Inhibitors Disrupt Mitochondrial Homeostasis and Promote Premature Endothelial Senescence. Toxicol Sci. 2019 Dec 1;172(2):445-456. doi: 10.1093/toxsci/kfz203.
• [11] Cerner Multum, Inc. "Australian Product Information.".
• [12] Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
• [13] Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
• [14] Cerner Multum, Inc. "UK Summary of Product Characteristics.".
• [15] Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
• [16] Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
• [17] Canadian Pharmacists Association.
• [18] Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
• [19] Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
• [20] Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
• [21] MHRA. Medicines and Healthcare Products Regulatory Agency "Orlistat: theoretical interaction with antiretroviral HIV medicines.".