Emtricitabine
Highest phase reached
Approved
Drug type
Small molecule
First approval year
2003
- First approval year
- 2003
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Emtricitabine
- Molecular weight
- 247.25
- Structure (SMILES)
- Nc1nc(=O)n([C@@H]2CS[C@H](CO)O2)cc1F
- emtricitabine component of atripla
- Emtricitabine component of atripla
- emtricitabine component of biktarvy
- Emtricitabine component of biktarvy
- emtricitabine component of complera
- Emtricitabine component of complera
- emtricitabine component of descovy
- Emtricitabine component of descovy
- emtricitabine component of eviplera
- Emtricitabine component of eviplera
- emtricitabine component of genvoya
- Emtricitabine component of genvoya
- emtricitabine component of odefsey
- Emtricitabine component of odefsey
- emtricitabine component of stribild
- Emtricitabine component of stribild
- emtricitabine component of symtuza
- Emtricitabine component of symtuza
- emtricitabine component of truvada
- Emtricitabine component of truvada
- emtriva
- Emtriva
- (-)-emtricitabine
- (-)-FTC
- 5 fluoro 1 2 hydroxymethyl 1 3 oxathiolan 5 yl cytosine 2r 5s
- 5-FLUORO-1-(2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)CYTOSINE (2R,5S)
- 524 w 91
- 524-W-91
- 524w91
- 524W91
- atripla component emtricitabine
- ATRIPLA COMPONENT EMTRICITABINE
- bw 524w91
- BW-524W91
- coviracil
- Coviracil
- descovy component emtricitabine
- DESCOVY COMPONENT EMTRICITABINE
- emtricitabina
- Emtricitabina
- emtricitabine
- Emtricitabine
- EMTRICITABINE [EMA EPAR]
- EMTRICITABINE [HSDB]
- emtricitabine [INN]
- EMTRICITABINE [JAN]
- EMTRICITABINE [MART.]
And 37 more, listed on the interactive page.
- ATC classification codes
- J05AF09
Sources for recorded values
- CAS registry numbers
- 143491-57-0
- ChEMBL ID
- CHEMBL885
- InChIKey
- XQSPYNMVSIKCOC-NTSWFWBYSA-N
- PubChem compound IDs
- 60877
- RxNorm IDs (RxCUI)
- 276237
- FDA ingredient codes (UNII)
- G70B4ETF4S
- Applicant
- GILEAD
- Approval date
- 2 Jul 2003
- Application number
- NDA021500
- Status
- Authorised
- Status date
- 24 Oct 2003
- Authorisation date
- 24 Oct 2003
- Approved indications
- Emtriva is indicated for the treatment of HIV-1 infected adults and children in combination with other antiretroviral agents. This indication is based on studies in treatment-naive patients and treatment-experienced patients with stable virological control. There is no experience of the use of Emtriva in patients who are failing their current regimen or who have failed multiple regimens. When deciding on a new regimen for patients who have failed an antiretroviral regimen, careful consideration should be given to the patterns of mutations associated with different medicinal products and the treatment history of the individual patient. Where available, resistance testing may be appropriate.
- Product number
- EMEA/H/C/000533
- Authorisation holder
- Gilead Sciences Ireland UC
- Priority medicines scheme
- No
- Generic
- No
- Biosimilar
- No
- Generic medicines
- 0
- Biosimilar medicines
- 0
- Advanced therapy
- No
- Conditional approval
- No
- Additional monitoring
- No
- Accelerated assessment
- No
- Exceptional circumstances
- No
Therapeutic areas
- HIV Infections
European medicines record
- Patents
- 0
- Designations
- 1
- First in class
- No
- Fast track
- Yes
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- No
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Boxed warning
- Yes
- Pharmacology name
- emtricitabine
- Type
- Synthetic organic
- Drug name stem
- -citabine
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
Mechanisms of action
- Mechanism
- Human immunodeficiency virus type 1 reverse transcriptase inhibitor
- Action type
- Inhibitor
- Target
- Human immunodeficiency virus type 1 reverse transcriptase
- Protein identifier
- Q72547
Open Targets mechanisms
- Mechanism
- Human immunodeficiency virus type 1 reverse transcriptase inhibitor
- Action type
- Inhibitor
- Target
- Human immunodeficiency virus type 1 reverse transcriptase
DrugCentral mechanisms
- Action type
- Inhibitor
- Gene symbol
- pol
- Protein identifier
- Q72547
- Organism
- Human immunodeficiency virus 1
- Condition
- HIV Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000180
- Subject identifier
- D015658
- Condition
- Infections
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000544
- Subject identifier
- D007239
- Condition
- Virus Diseases
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000763
- Subject identifier
- D014777
- Condition
- HIV Infections
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000764
- Subject identifier
- D015658
- Condition
- Acquired Immunodeficiency Syndrome
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000765
- Subject identifier
- D000163
- Condition
- Insulin Resistance
- Highest recorded phase
- 1
- Condition identifier
- EFO:0002614
- Subject identifier
- D007333
- Condition
- Hepatitis C
- Highest recorded phase
- 1
- Condition identifier
- EFO:0003047
- Subject identifier
- D006526
- Condition
- Hepatitis B, Chronic
- Highest recorded phase
- 3
- Condition identifier
- EFO:0004197
- Subject identifier
- D019694
- Condition
- Hepatitis B, Chronic
- Highest recorded phase
- 3
- Condition identifier
- EFO:0004239
- Subject identifier
- D019694
- Condition
- Liver Cirrhosis, Biliary
- Highest recorded phase
- 2
- Condition identifier
- EFO:1001486
- Subject identifier
- D008105
- Condition
- Multiple Sclerosis
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0005301
- Subject identifier
- D009103
- Condition
- Tuberculosis
- Highest recorded phase
- 1
- Condition identifier
- MONDO:0018076
- Subject identifier
- D014376
- Condition
- Severe Acute Respiratory Syndrome
- Highest recorded phase
- 3
- Condition identifier
- MONDO:0100096
- Subject identifier
- D045169
- Condition identifier
- EFO_0000180
- Condition identifier
- EFO_0000180
- Highest recorded phase
- 4
- Condition identifier
- EFO_0000544
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000763
- Condition identifier
- EFO_0000764
- Condition identifier
- EFO_0000765
- Highest recorded phase
- 3
- Condition identifier
- EFO_0004197
- Highest recorded phase
- 3
- Condition identifier
- EFO_0004239
- Highest recorded phase
- 3
- Condition identifier
- EFO_0009878
- Condition identifier
- EFO_0010702
- Condition identifier
- EFO_1001486
- Highest recorded phase
- 2
- Condition identifier
- HP_0001513
- Highest recorded phase
- 3
- Condition identifier
- HP_0003124
- Highest recorded phase
- 2
- Condition identifier
- HP_0025502
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0004975
- Highest recorded phase
- 1
- Condition identifier
- MONDO_0005055
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0005108
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0005109
- Highest recorded phase
- 4
- Condition identifier
- MONDO_0005136
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0005231
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0005249
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005301
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005344
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0005366
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0005388
- Highest recorded phase
- 2
And 11 more, listed on the interactive page.
Warnings
- Warning
- Black Box Warning
- Effect
- hepatotoxicity
Open Targets warnings
- Warning
- Black Box Warning
- Effect
- hepatotoxicity
- Country
- United States
- Event
- abortion spontaneous
- Reports
- 359
- Reporting signal score
- 392.221
- Event
- acute hiv infection
- Reports
- 80
- Reporting signal score
- 366.57
- Event
- blood creatinine increased
- Reports
- 305
- Reporting signal score
- 202.647
- Event
- blood hiv rna increased
- Reports
- 192
- Reporting signal score
- 699.751
- Event
- cd4 lymphocytes decreased
- Reports
- 98
- Reporting signal score
- 250.513
- Event
- drug resistance
- Reports
- 447
- Reporting signal score
- 783.771
- Event
- fanconi syndrome acquired
- Reports
- 124
- Reporting signal score
- 364.853
- Event
- genotype drug resistance test positive
- Reports
- 111
- Reporting signal score
- 322.195
- Event
- immune reconstitution inflammatory syndrome
- Reports
- 311
- Reporting signal score
- 828.323
- Event
- immune reconstitution syndrome
- Reports
- 73
- Reporting signal score
- 199.002
- Event
- lipodystrophy acquired
- Reports
- 91
- Reporting signal score
- 220.482
- Event
- osteoporosis
- Reports
- 250
- Reporting signal score
- 376.732
- Event
- pathogen resistance
- Reports
- 134
- Reporting signal score
- 212.708
- Event
- premature baby
- Reports
- 249
- Reporting signal score
- 253.707
- Event
- product dispensing error
- Reports
- 175
- Reporting signal score
- 325.797
- Event
- renal tubular disorder
- Reports
- 151
- Reporting signal score
- 373.118
- Event
- stillbirth
- Reports
- 115
- Reporting signal score
- 234.859
- Event
- viral load increased
- Reports
- 234
- Reporting signal score
- 737.394
- Event
- viral mutation identified
- Reports
- 169
- Reporting signal score
- 416.03
- Event
- virologic failure
- Reports
- 384
- Reporting signal score
- 1,072.48
- NCT00002335
- NCT00002362
- NCT00002416
- NCT00006144
- NCT00006208
- NCT00016718
- NCT00017992
- NCT00036452
- NCT00039741
- NCT00043966
- NCT00074581
- NCT00076791
- NCT00084136
- NCT00089505
- NCT00090779
- NCT00099632
- NCT00102206
- NCT00105079
- NCT00106379
- NCT00112047
- NCT00115609
- NCT00118898
- NCT00158457
- NCT00192634
- NCT00196599
And 295 more, listed on the interactive page.
- Dose
- 200 mg / 300 mg
- Route
- Oral
- How often
- Once daily
Conditions of use
- Take with or without food
- Hydrogen bond acceptors
- 7
- Hydrogen bond donors
- 2
- Polar surface area
- 90.37
- Calculated partition coefficient (ALogP)
- -0.46
- Calculated partition coefficient (XLogP)
- -0.6
- Prodrug
- Yes
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Molecular formula
- C8H10FN3O3S
- Monoisotopic mass
- 247.04269053
- Natural product
- No
- 0093-5234
- 0093-7704
- 0378-5440
- 0904-7172
- 16714-534
- 31722-560
- 31722-736
- 33342-106
- 33342-138
- 42291-980
- 42385-801
- 42385-915
- 42385-953
- 42543-719
- 51407-112
- 59651-165
- 59651-166
- 59651-167
- 59676-800
- 64380-719
- 65862-301
- 65862-354
- 65862-497
- 68180-287
- 69097-209
And 48 more, listed on the interactive page.
- Recorded assays
- 1,099
- Active assays
- 47
- Confirmatory
- Screening
- Antiviral Agents
- Reverse Transcriptase Inhibitors
- Anti-HIV Agents
Oral bioavailability
- Median
- 93
- Mean
- 82
- Minimum
- 60
- Maximum
- 93
- Unit
- %
- Assays
- 3
- Standard deviation
- 19.0526
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- F
Related records
Trials (388)
- (mo)BETTA Trial in Transwomen for Optimization of ART
- A Bioequivalence Study of Darunavir, Emtricitabine, and Tenofovir Alafenamide, in the Presence of Cobicistat in Healthy Participants
- A Clinical Study of Islatravir and Ulonivirine for People With HIV-1 Who Have Not Been Treated Before (MK-8591B-062)
- A Clinical Study of MK-8527 to Prevent Human Immunodeficiency Virus Type 1 (HIV-1) (MK-8527-011)
- A Clinical Trial Comparing the Efficacy of Tenofovir Disoproxil Fumarate/Emtricitabine/Rilpivirine (TDF/FTC/RPV) Versus TDF/FTC/Efavirenz (TDF/FTC/EFV) in Patients With Undetectable Plasma HIV-1 RNA on Current First-line Treatment
- A Clinical Trial of MK-4646 With Bictegravir/Emtricitabine/Tenofovir Alafenamide and Dolutegravir in Healthy Adult Participants (MK-4646)
- A Clinical Trial to Evaluate the Reversibility of Abacavir/Lamivudine/Dolutegravir CNS-Related Neurotoxicity After Switching to Tenofovir/Alafenamide/Emtricitabine/Darunavir/Cobicistat (TAF/FTC/DRV/c)
- A Comparison of Emtricitabine and Abacavir Used in a Three-Drug Combination in HIV-Infected Patients Who Have Never Taken Anti-HIV Drugs
- A Comparison of Emtricitabine and Stavudine Used With Didanosine Plus Efavirenz in HIV-Infected Patients Who Have Not Taken Anti-HIV Drugs
- A Comparison of Two Anti-HIV Drug Regimens for Youth Who Have Failed Prior Therapy
- A Demonstration Project to Add Pre- or Post-exposure Prophylaxis to Combination HIV Prevention Services
- A Dose-Range Finding Clinical Trial Study in Human Immunodeficiency Virus (HIV-1) Infected Treatment-Naive Adults
- A Key Link for Transmission Prevention
- A Pharmacist-run PrEP Program for Women
- A Pharmacokinetic Evaluation of Tenofovir/Emtricitabine as HIV Pre-Exposure Prophylaxis in Transgender Women
- A Phase 2b Study Evaluating Oral VH4524184 Regimens in Treatment Naïve Persons With HIV-1 (INNOVATE Study)
- A Phase IV, Open-label, Randomised, Pilot Clinical Trial Designed to Evaluate the Potential Neurotoxicity of Dolutegravir/Lamivudine/Abacavir in Neurosymptomatic HIV Patients and Its Reversibility After Switching to Elvitegravir/Cobicistat/Emtricitabine/Tenofovir Alafenamide. DREAM Study
- A Pilot Study of Pre-Exposure Prophylaxis (PrEP) to Evaluate Safety, Acceptability, and Adherence in At-Risk Populations in Kenya, Africa
- A Pilot Study of Pre-Exposure Prophylaxis (PrEP) to Evaluate Safety, Acceptability, and Adherence in At-risk Populations in Uganda, Africa
- A Pilot Study to Assess the Feasibility of Switching, Individuals Receiving Atripla With Continuing Central Nervous System (CNS) Toxicity, to a Fixed Dose Combination of Tenofovir/Emtricitabine/Rilpivirine
Approved for (2)
In development for (8)
- AIDS Phase 3
- Chronic hepatitis B virus infection Phase 3
- COVID-19 Phase 3
- Hepatitis B virus infection Phase 3
- Hepatitis C virus infection Phase 1
- Multiple sclerosis Phase 2
- Primary biliary cholangitis Phase 2
- Tuberculosis Phase 1
Other linked conditions (1)
- Aicardi-Goutieres syndrome