Emtricitabine

Summary

Emtricitabine (CHEMBL885) is an approved small-molecule antiviral drug (ATC J05AF09); indicated across 13 conditions including hiv infectious disease and viral infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J05AF09
• Indications: 13 conditions
• Clinical trials: 292
• Chemistry: 247.25 Da · C8H10FN3O3S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL885
Name	Emtricitabine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	60877
ChEBI	CHEBI:31536
ATC	J05AF09
Molecular formula	C8H10FN3O3S
Molecular weight	247.25
InChIKey	XQSPYNMVSIKCOC-NTSWFWBYSA-N

SMILES: C1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F

IUPAC name: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one

ChEBI definition: An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection.

Pharmacological roles (ChEBI): antiviral drug, HIV-1 reverse transcriptase inhibitor.

Also known as: (-)-emtricitabine, (-)-FTC, 524W91, BW-524W91, Coviracil, Emtricitabina, Emtricitabine, Emtricitabine component of atripla, Emtricitabine component of biktarvy, Emtricitabine component of complera, Emtricitabine component of descovy, Emtricitabine component of eviplera

Patent coverage: 6,206 distinct patent families (24,316 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Albumin.

Bioactivity

No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

2 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
HIV infectious disease	4	MONDO:0005109	EFO:0000180
viral infectious disease	4	MONDO:0005108	EFO:0000763

8 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
chronic hepatitis B virus infection	3	MONDO:0005366	EFO:0004239
AIDS	3	MONDO:0012268	EFO:0000765
hepatitis B virus infection	3	MONDO:0005344	EFO:0004197
severe acute respiratory syndrome	3	MONDO:0005091	MONDO:0100096
primary biliary cholangitis	2	MONDO:0005388	EFO:1001486
multiple sclerosis	2	MONDO:0005301	MONDO:0005301
hepatitis C virus infection	1	MONDO:0005231	EFO:0003047
tuberculosis	1	MONDO:0018076	MONDO:0018076

3 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 292.

Phase distribution

Phase	Trials
PHASE4	78
PHASE3	71
PHASE2	52
Not specified	43
PHASE1	28
PHASE2/PHASE3	9
PHASE1/PHASE2	8
EARLY_PHASE1	3

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02656511	PHASE4	ACTIVE_NOT_RECRUITING	Immediate Initiation of Antiretroviral Therapy During Hyperacute HIV Infection
NCT04616963	PHASE4	ACTIVE_NOT_RECRUITING	Emtricitabine/Tenofovir Alafenamide Switch Study for Transgender Individuals for HIV Pre-exposure Prophylaxis
NCT06374758	PHASE4	RECRUITING	Accelerated ART Initiation for PWHIV Who Are Out of Care
NCT06830668	PHASE4	NOT_YET_RECRUITING	Same-Day Restart of B/F/TAF in HIV Patients After NNRTI Discontinuation
NCT07006246	PHASE4	ACTIVE_NOT_RECRUITING	Utilizing Private Pharmacies to Initiate High-risk Young Individuals on PrEP in South Africa
NCT00055120	PHASE4	COMPLETED	When to Start Anti-HIV Drugs in Patients With Opportunistic Infections
NCT00084136	PHASE4	COMPLETED	Prospective Evaluation of Anti-retroviral Combinations for Treatment Naive, HIV Infected Persons in Resource-limited Settings
NCT00106379	PHASE4	COMPLETED	Tenofovir DF (Disoproxil Fumarate) in Combination With Emtricitabine in HIV-1 Patients
NCT00127959	PHASE4	COMPLETED	Virological and Clinical Anti-Hepatitis B Virus (HBV) Efficacy of Tenofovir and Emtricitabine in Patients With HIV/HBV co-Infection
NCT00244712	PHASE4	COMPLETED	Abacavir/Lamivudine Versus Emtricitabine/Tenofovir Both In Combination With Lopinavir/Ritonavir For The Treatment Of HIV
NCT00389194	PHASE4	COMPLETED	PREventing Progression of Adipose Tissue Redistribution
NCT00442962	PHASE4	COMPLETED	HIV Treatment Reinitiation in Women Who Received Anti-HIV Drugs to Prevent Mother-to-Child Transmission of HIV
NCT00532168	PHASE4	COMPLETED	Once-daily Antiretroviral Therapy in HIV-1 Infected Patients With CD4+ Cell Counts Below 100 Cells/Mcl
NCT00544128	PHASE4	COMPLETED	Comparison of Epzicom and Truvada for the Initial Once Daily HIV Treatment
NCT00615745	PHASE4	COMPLETED	ONCE - Only Nocturnal Combination Evaluation of Antiretroviral-Experienced HIV 1 Infected Subjects Switching to Atripla
NCT00677300	PHASE4	COMPLETED	Raltegravir And Darunavir Antiretroviral in Antiretroviral Naive Patients
NCT00759070	PHASE4	UNKNOWN	Effects of 2 Initial Standard Antiretroviral Combinations Therapies on Lipid Metabolism
NCT00869960	PHASE4	COMPLETED	Impact of Menstrual Cycle on Antiretroviral Pharmacokinetics in Healthy Women
NCT00931801	PHASE4	COMPLETED	BATAR: Individuals Currently Taking Boosted Atazanavir as Part of an HIV Treatment Regimen Will be Evaluated to See if Substituting Raltegravir for Nucleoside Transcriptase Inhibitors Will be Safe and Well Tolerated.
NCT01025427	PHASE4	COMPLETED	HIV Persistence and Viral Reservoirs
NCT01234116	PHASE4	COMPLETED	Post-Exposure Prophylaxis in Health Care Workers
NCT01270802	PHASE4	COMPLETED	Effects of Switching Efavirenz to Raltegravir on Vascular Function and Bone Markers in HIV-infected Patients
NCT01274780	PHASE4	COMPLETED	Metabolic Effects of Atazanavir/Ritonavir Versus Darunavir/Ritonavir in Combination With Tenofovir/Emtricitabine in naïve HIV-1 Infected Patients
NCT01285050	PHASE4	COMPLETED	Interferon Alfa Sensitivity in HIV/HCV Persons Before and After HIV Meds
NCT01332227	PHASE4	COMPLETED	Atazanavir/Ritonavir, Once Daily + Raltegravir, Twice Daily, Switch Study in HIV-1-Infected Patients
NCT01335620	PHASE4	COMPLETED	The Safety, Pharmacokinetic Profile and Efficacy of Raltegravir in HIV-infected Patients at Least 60 Years of Age
NCT01529749	PHASE4	COMPLETED	Effects of Losartan and Antiretroviral Regimen Containing Raltegravir in Fibrosis Inflammation Mediators, Cardiovascular Risk and Neurocognitive Disorders in HIV Infected Patients Previously Effectively Treated
NCT01533272	PHASE4	COMPLETED	Study Comparing Two Alternatives of Antiretroviral Therapy as Post-exposure Prophylaxis to HIV-1:FOVIR+EMTRICITABINA + LOPINAVIR/RITONAVIR VS TENOFOVIR+EMTRICITABINA + MARAVIROC (MARAVI-PEP)
NCT01576731	PHASE4	COMPLETED	Study Comparing Two Alternatives of Antiretroviral Therapy as Post-exposure Prophylaxis to HIV-1: Tenofovir + Emtricitabine + Lopinavir/Ritonavir Versus Tenofovir + Emtricitabine + Raltegravir (RAL-PEP)
NCT01641367	PHASE4	COMPLETED	A5288/MULTI-OCTAVE: Management Using Latest Technologies to Optimize Combination Therapy After Viral Failure
NCT01772940	PHASE4	COMPLETED	Nevirapine vs Ritonavir-boosted Lopinavir in ART Naive HIV-infected Adults in a Resource Limited Setting
NCT01777997	PHASE4	COMPLETED	FTC/RPV/TDF on T-Cell Activation, CD4+ T-Cell Count, Inflammatory Biomarkers and Viral Reservoir
NCT01781806	PHASE4	COMPLETED	A Demonstration Project to Add Pre- or Post-exposure Prophylaxis to Combination HIV Prevention Services
NCT01855867	PHASE4	COMPLETED	HIV Non-Occupational Post-Exposure Prophylaxis
NCT02042001	PHASE4	COMPLETED	Switching From Efavirenz/Atripla to Rilpivirine Among Patients With Neurocognitive or Neuropsychological Side Effects
NCT02149888	PHASE4	COMPLETED	PRe-Exposure Prophylaxis Acceptability & Readiness Assessments for Toronto gaY, Bisexual and Other Men Who Have Sex With Men-5
NCT02159599	PHASE4	COMPLETED	Study to Evaluate Darunavir/Ritonavir + Lamivudine Versus Continuing With Darunavir/Ritonavir + Tenofovir/Emtricitabine or Abacavir/Lamivudine in HIV Infected Subject
NCT02180438	PHASE4	COMPLETED	An Open Label Trial of Stribild for Antiretroviral (ARV)-naïve HIV-2 Infected Adults in Dakar, Senegal
NCT02198443	PHASE4	COMPLETED	Comparison of Two Combinations in Antiretroviral Post-Exposure Prophylaxis for HIV-1: Tenofovir/Emtricitabine (Truvada ®) + Lopinavir/Ritonavir (Kaletra ®) vs Tenofovir/Emtricitabine/Cobicistat/Elvitegravir (Stribild ®). Prospective, Randomized, Open.
NCT02206555	PHASE4	COMPLETED	PrEP Demonstration Project (PRELUDE Study)
NCT02285374	PHASE4	UNKNOWN	Efavirenz to Dolutegravir Switch in Patients With CNS Toxicity
NCT02327663	PHASE4	UNKNOWN	Emtricitabine for Naive Chinese Chronic Hepatitis B Patients
NCT02327676	PHASE4	UNKNOWN	Emtricitabine for Naive Child Chinese Chronic Hepatitis B Patients
NCT02327702	PHASE4	UNKNOWN	Emtricitabine for Naive Chinese Pregnant Chronic Hepatitis B Patients
NCT02327715	PHASE4	UNKNOWN	Emtricitabine for Prevention of Vertical Transmission of HBV in Chinese Pregnant HBsAg Positive Patients
NCT02447016	PHASE4	TERMINATED	Decrease of Neuropsychiatric Side Effects After Switching From Atripla to Eviplera
NCT02470650	PHASE4	WITHDRAWN	Cost-effectiveness of Different Antiretroviral Treatment in Patients HIV Naive
NCT02547844	PHASE4	COMPLETED	Evolution of Plasma Lipid Profile in Patients With HIV1 Who Change Atripla to Eviplera Compared to Continue With Atripla
NCT02593409	PHASE4	UNKNOWN	HIV PrEP Priming of Immune Effectors
NCT02771054	PHASE4	COMPLETED	Tenofovir Alafenamide Fumarate (TAF) Effect on Residual Intrathecal Immune Activation
NCT03058835	PHASE4	UNKNOWN	IN-US-276-1340: Pre-Exposure Prophylaxis to Prevent HIV Acquisition in US Women: A Demonstration Project
NCT03067285	PHASE4	COMPLETED	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
NCT03120494	PHASE4	UNKNOWN	Evaluating the Feasibility and Acceptability of Implementing a PrEP Program in PR-CoNCRA (San Juan, Puerto Rico)- Part B
NCT03120936	PHASE4	COMPLETED	The Stay Study: A Demonstration Project Advancing PrEP Delivery in the San Francisco Bay Area Transgender Community
NCT03160105	PHASE4	COMPLETED	Evaluation of a Simplified Strategy for the Long-term Management of HIV Infection (Simpl’HIV)
NCT03220152	PHASE4	UNKNOWN	Implementation of PrEP to HIV in Brazilian Transgender Women
NCT03309566	PHASE4	COMPLETED	Bioequivalence Study of Two Formulatiosns With the Asscociaton of Efavirenz, Emtricitabine and Tenofovir
NCT03348163	PHASE4	TERMINATED	(mo)BETTA Trial in Transwomen for Optimization of ART
NCT03350672	PHASE4	COMPLETED	Validation of a Urine Assay to Measure Tenofovir Levels in Patients Taking Tenofovir Alafenamide
NCT03360682	PHASE4	COMPLETED	Clinical Trial to Evaluate the Efficacy, Pharmacokinetics (PK) Interactions and Safety of Dolutegravir Plus 2 Nucleoside Reverse Transcriptase Inhibitors (NRTIs) in HIV-1-Infected Solid Organ Transplant Patients
NCT03387462	PHASE4	COMPLETED	DOT Diary Optimization Pilot: A Pilot Study to Optimize the DOT Diary App to Measure PrEP Adherence
NCT03464266	PHASE4	COMPLETED	The Kampala Women’s Bone Study
NCT03502005	PHASE4	COMPLETED	Efficacy, Safety & Tolerability of Switching EFV/TDF/FTC to BIC/FTC/TAF in Virologically Suppressed Adults With HIV-1
NCT03685500	PHASE4	COMPLETED	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)
NCT03771638	PHASE4	COMPLETED	DOT Diary Mobile App for Pre-Exposure Prophylaxis Adherence in Young Men
NCT03998176	PHASE4	COMPLETED	Bictegravir/Emtricitabine/Tenofovir Alafenamide (B/F/TAF) in HIV-1 Infected Patients With Active Illicit Substance usE
NCT04050371	PHASE4	COMPLETED	Study of Truvada for HIV Pre Exposure Prophylaxis Using Daily Directly Observed Therapy to Look at Potential Interactions Between Truvada and Hormone Therapy
NCT04132674	PHASE4	UNKNOWN	Switching to a Fixed Dose Combination of Bictegravir/Emtricitabine/Tenofovir Alafenamide (B/F/TAF) in HIV-1 Infected Marginalized Populations Who Are Virologically Suppressed
NCT04240509	PHASE4	UNKNOWN	Defining the PrEP Care Continuum Among Recently Incarcerated Men at High-Risk for HIV Infection
NCT04249037	PHASE4	TERMINATED	Rapid Start vs. Standard Start Antiretroviral Therapy (ART) in HIV
NCT04388904	PHASE4	COMPLETED	Rapid Reinitiation of a Single Tablet Antiretroviral Therapy Using Symtuza® in HIV-1 Infected Treatment-Experienced Patients Off Therapy. (ReSTART)
NCT04538040	PHASE4	COMPLETED	Bictegravir/Emtricitabine/Tenofovir Alafenide Plus Doravirine
NCT04549467	PHASE4	COMPLETED	Efficacy of Dolutegravir Plus Lamivudine in HIV-1-infected Treatment-naïve Adults Without a Baseline Genotyping Test
NCT04585737	PHASE4	COMPLETED	Efficacy of Switching to DTG/3TC in Virologically-suppressed Adults Currently on B/F/TAF
NCT04636437	PHASE4	COMPLETED	Doravirine for Obese Persons on Integrase Inhibitors and Tenofovir Alafenamide
NCT04884139	PHASE4	COMPLETED	DTG/3TC vs. BIC/FTC/TAF Maintenance Therapy in People Living With HIV:
NCT05606055	PHASE4	COMPLETED	The Benefits of Immediate Treatment Initiation Without Immunovirological Data Compared to Conventional BIC / FTC / TAF Treatment in Naive Patients With Type 1 HIV (Human Immunodeficiency Virus) Infection
NCT06177574	PHASE4	COMPLETED	Study of Bictegravir/Emtricitavine/Tenofovir Alafenamide in HIV-1 Infected naïve Patients Using Test and Treat Stategy Rapid-initiation Model of Care: BIC-NOW Clinical Trial (BIC-NOW)
NCT03164564	PHASE3	ACTIVE_NOT_RECRUITING	Evaluating the Safety and Efficacy of Long-Acting Injectable Cabotegravir Compared to Daily Oral TDF/FTC for Pre-Exposure Prophylaxis in HIV-Uninfected Women
NCT05630755	PHASE3	ACTIVE_NOT_RECRUITING	A Switch to Doravirine/Islatravir (DOR/ISL) in Participants With Human Immunodeficiency Virus Type 1 (HIV-1) Who Are Virologically Suppressed on Bictegravir/Emtricitabine/Tenofovir Alafenamide (BIC/FTC/TAF) (MK-8591A-052)
NCT05705349	PHASE3	ACTIVE_NOT_RECRUITING	DOR/ISL in HIV-1 Antiretroviral Treatment-naïve Participants (MK-8591A-053)
NCT05979311	PHASE3	ACTIVE_NOT_RECRUITING	A Study to Evaluate the Efficacy, Safety, and Tolerability of Using an Oral Once-daily 2 Drug Regimen Compared to an Oral Once-daily 3 Drug Regimen for the Treatment of Human Immunodeficiency Virus (HIV)-1 in Adults Who Have Not Previously Taken Antiretroviral Therapy
NCT06544733	PHASE2/PHASE3	ACTIVE_NOT_RECRUITING	Study of Oral Weekly Lepetegravir (Formerly GS-1720) and Lenacapavir Pacfosacil (Formerly GS-4182) Versus Biktarvy in People With HIV-1 Who Are Virologically Suppressed
NCT07044297	PHASE3	RECRUITING	A Clinical Study of MK-8527 to Prevent Human Immunodeficiency Virus Type 1 (HIV-1) (MK-8527-011)
NCT07071623	PHASE3	RECRUITING	A Study of MK-8527 to Prevent Human Immunodeficiency Virus Type 1 (HIV-1) (MK-8527-010)
NCT07075146	PHASE3	RECRUITING	DOR/TDF/3TC COmpared With BIC/FTC/TAF in ART-Naïve People Living With HIV and Overweight or Obesity
NCT07266831	PHASE2/PHASE3	RECRUITING	A Clinical Study of Islatravir and Ulonivirine for People With HIV-1 Who Have Not Been Treated Before (MK-8591B-062)
NCT00002362	PHASE3	SUSPENDED	A Comparison of Emtricitabine and Abacavir Used in a Three-Drug Combination in HIV-Infected Patients Who Have Never Taken Anti-HIV Drugs
NCT00002416	PHASE3	COMPLETED	Comparing FTC and Lamivudine in HIV-Infected Patients on a Stable Anti-HIV Drug Combination
NCT00006208	PHASE3	UNKNOWN	A Comparison of Emtricitabine and Stavudine Used With Didanosine Plus Efavirenz in HIV-Infected Patients Who Have Not Taken Anti-HIV Drugs
NCT00043966	PHASE3	COMPLETED	Study of Lopinavir, Ritonavir, Tenofovir and Emtricitabine in HIV-Infected Antiretroviral Naïve Subjects
NCT00074581	PHASE3	COMPLETED	Preventing Sexual Transmission of HIV With Anti-HIV Drugs
NCT00089505	PHASE3	COMPLETED	NNRTI vs PI Regimens for HIV Infected Women After They Have Taken Nevirapine to Prevent Mother-To-Child HIV Transmission
NCT00105079	PHASE3	COMPLETED	GEMINI Study - A Study of Saquinavir/Ritonavir in Treatment-Naive Patients With HIV-1 Infection
NCT00112047	PHASE3	COMPLETED	Tenofovir Disoproxil Fumarate/Emtricitabine/Efavirenz Versus Combivir/Efavirenz in Antiretroviral-Naive HIV-1 Infected Subjects
NCT00115609	PHASE3	COMPLETED	Efficacy of Tenofovir-Emtricitabine and Efavirenz in HIV Infected Patients With Tuberculosis (ANRS129)
NCT00116805	PHASE3	COMPLETED	A Study to Compare Tenofovir Disoproxil Fumarate Versus Adefovir Dipivoxil for the Treatment of HBeAg-Positive Chronic Hepatitis B
NCT00117676	PHASE3	COMPLETED	A Study to Compare Tenofovir Disoproxil Fumarate Versus Adefovir Dipivoxil for the Treatment of HBeAg-Negative Chronic Hepatitis B
NCT00118898	PHASE3	COMPLETED	Efavirenz or Atazanavir/Ritonavir Given With Emtricitabine/Tenofovir Disoproxil Fumarate or Abacavir/Lamivudine in HIV Infected Treatment-Naive Adults
NCT00158457	PHASE3	COMPLETED	Simple Once Daily Triple Regimen Including Tenofovir, Emtricitabine and Efavirenz in HIV-1 Infected Patients (ANRS 1207)

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 1 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).