emtricitabine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
nucleosides antiviral or antineoplastic agents, cytarabine or azacitidine derivatives	1003	143491-57-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: emtricitabine coviracil emtriva	A deoxycytidine analog and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B viruses. It is used to treat HIV INFECTIONS. Molecular weight: 247.24 Formula: C8H10FN3O3S CLOGP: -1.29 LIPINSKI: 0 HAC: 6 HDO: 2 TPSA: 88.15 ALOGS: -2.09 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

emtricitabine
coviracil
emtriva

A deoxycytidine analog and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B viruses. It is used to treat HIV INFECTIONS.

Molecular weight: 247.24
Formula: C8H10FN3O3S
CLOGP: -1.29
LIPINSKI: 0
HAC: 6
HDO: 2
TPSA: 88.15
ALOGS: -2.09
ROTB: 2

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.20	g	O

ADMET properties:

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Property	Value	Reference
EoM (Fraction excreted unchanged in urine)	73 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	112 mg/mL	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	11.56 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
fu (Fraction unbound in plasma)	1 %	Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K

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Approvals:

Date	Agency	Company
July 2, 2003	FDA	GILEAD
March 23, 2005	PMDA	Japan Tobacco Inc.
Oct. 24, 2003	EMA

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Abortion spontaneous	745.53	21.21	282	10048	46913	63431779
Exposure during pregnancy	511.22	21.21	316	10014	155231	63323461
Foetal exposure during pregnancy	450.45	21.21	176	10154	31786	63446906
Abortion induced	344.73	21.21	108	10222	10134	63468558
Immune reconstitution inflammatory syndrome	237.89	21.21	72	10258	6012	63472680
Stillbirth	230.51	21.21	72	10258	6678	63472014
Virologic failure	221.15	21.21	53	10277	1809	63476883
Blood HIV RNA increased	215.92	21.21	44	10286	695	63477997
Pregnancy	204.99	21.21	106	10224	36730	63441962
Premature baby	196.20	21.21	86	10244	20649	63458043

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Immune reconstitution inflammatory syndrome	819.45	13.85	274	20461	8485	34927711
Psychiatric decompensation	406.99	13.85	124	20611	2813	34933383
Depression suicidal	314.23	13.85	98	20637	2407	34933789
Tearfulness	308.19	13.85	98	20637	2569	34933627
Virologic failure	286.46	13.85	99	20636	3381	34932815
Blood HIV RNA increased	273.32	13.85	75	20660	1155	34935041
Drug interaction	265.45	13.85	477	20258	225469	34710727
Depressive symptom	265.36	13.85	89	20646	2770	34933426
Fanconi syndrome acquired	245.98	13.85	77	20658	1914	34934282
Psychomotor skills impaired	227.30	13.85	86	20649	3820	34932376

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Immune reconstitution inflammatory syndrome	1019.10	15.26	303	22368	13538	79708179
Abortion spontaneous	587.97	15.26	244	22427	29263	79692454
Psychiatric decompensation	450.99	15.26	122	22549	3841	79717876
Virologic failure	444.23	15.26	122	22549	4069	79717648
Drug interaction	431.14	15.26	558	22113	414625	79307092
Blood HIV RNA increased	417.27	15.26	98	22573	1710	79720007
Viral mutation identified	416.77	15.26	114	22557	3744	79717973
Depression suicidal	348.48	15.26	99	22572	3743	79717974
Drug resistance	322.78	15.26	181	22490	42032	79679685
Tearfulness	304.24	15.26	99	22572	5946	79715771

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J05AF09	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Nucleoside and nucleotide reverse transcriptase inhibitors
ATC	J05AR03	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR06	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR08	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR09	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR17	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR18	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR19	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR20	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR22	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Human immunodeficiency virus infection	indication	86406008	DOID:526
Coronavirus infection	off-label use	186747009
Prevention of HIV Infection after Exposure	off-label use
Osteomalacia	contraindication	4598005	DOID:10573
Hypophosphatemia	contraindication	4996001
Suicidal thoughts	contraindication	6471006
Hypercholesterolemia	contraindication	13644009
Torsades de pointes	contraindication	31722008
Depressive disorder	contraindication	35489007
Fanconi syndrome	contraindication	40488004	DOID:1062

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	12.95	acidic
pKa2	2.57	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
120MG;EQ 15MG BASE	DESCOVY	GILEAD SCIENCES INC	N208215	Jan. 7, 2022	RX	TABLET	ORAL	8754065	Aug. 15, 2032	TREATMENT OF HIV-1 INFECTION
120MG;EQ 15MG BASE	DESCOVY	GILEAD SCIENCES INC	N208215	Jan. 7, 2022	RX	TABLET	ORAL	9296769	Aug. 15, 2032	TREATMENT OF HIV-1 INFECTION
150MG;150MG;200MG;300MG	STRIBILD	GILEAD SCIENCES INC	N203100	Aug. 27, 2012	RX	TABLET	ORAL	8592397	Jan. 13, 2024	TREATMENT OF HIV INFECTION
150MG;150MG;200MG;300MG	STRIBILD	GILEAD SCIENCES INC	N203100	Aug. 27, 2012	RX	TABLET	ORAL	8716264	Jan. 13, 2024	TREATMENT OF HIV INFECTION
150MG;150MG;200MG;300MG	STRIBILD	GILEAD SCIENCES INC	N203100	Aug. 27, 2012	RX	TABLET	ORAL	9457036	Jan. 13, 2024	TREATMENT OF HIV INFECTION
150MG;150MG;200MG;300MG	STRIBILD	GILEAD SCIENCES INC	N203100	Aug. 27, 2012	RX	TABLET	ORAL	9744181	Jan. 13, 2024	TREATMENT OF HIV INFECTION
150MG;150MG;200MG;300MG	STRIBILD	GILEAD SCIENCES INC	N203100	Aug. 27, 2012	RX	TABLET	ORAL	7176220	Aug. 27, 2026	TREATMENT OF HIV INFECTION
150MG;150MG;200MG;300MG	STRIBILD	GILEAD SCIENCES INC	N203100	Aug. 27, 2012	RX	TABLET	ORAL	7635704	Oct. 26, 2026	TREATMENT OF HIV INFECTION
150MG;150MG;200MG;300MG	STRIBILD	GILEAD SCIENCES INC	N203100	Aug. 27, 2012	RX	TABLET	ORAL	8148374	Sept. 3, 2029	TREATMENT OF HIV INFECTION USING A COMPOSITION CONTAINING A PHARMACOKINETIC ENHANCER THAT INHIBITS CYTOCHROME P450 MONOOXYGENASE
150MG;150MG;200MG;300MG	STRIBILD	GILEAD SCIENCES INC	N203100	Aug. 27, 2012	RX	TABLET	ORAL	9891239	Sept. 3, 2029	TREATMENT OF HIV INFECTION

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
200MG;EQ 25MG BASE	DESCOVY	GILEAD SCIENCES INC	N208215	April 4, 2016	RX	TABLET	ORAL	Sept. 28, 2024	IN COMBINATION WITH OTHER ANTIRETROVIRAL AGENTS, FOR THE TREATMENT OF HIV-1 INFECTION IN PEDIATRIC PATIENTS UNDER 12 YEARS OF AGE WEIGHING AT LEAST 35KG
200MG;EQ 25MG BASE	DESCOVY	GILEAD SCIENCES INC	N208215	April 4, 2016	RX	TABLET	ORAL	Sept. 28, 2024	IN COMBINATION WITH OTHER ANTIRETROVIRAL AGENTS OTHER THAN PROTEASE INHIBITORS THAT REQUIRE A CYP3A INHIBITOR, FOR THE TREATMENT OF HIV-1 INFECTION IN PEDIATRIC PATIENTS UNDER 12 YEARS OF AGE WEIGHING AT LEAST 25KG AND LESS THAN 35KG
EQ 30MG BASE;120MG;EQ 15MG BASE	BIKTARVY	GILEAD SCIENCES INC	N210251	Oct. 7, 2021	RX	TABLET	ORAL	Feb. 7, 2023	NEW CHEMICAL ENTITY
EQ 30MG BASE;120MG;EQ 15MG BASE	BIKTARVY	GILEAD SCIENCES INC	N210251	Oct. 7, 2021	RX	TABLET	ORAL	Oct. 7, 2028	A COMPLETE REGIMEN FOR THE TREATMENT OF HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 (HIV-1) INFECTION IN PEDIATRIC PATIENTS WEIGHING 14 KG TO LESS THAN 25 KG WHO HAVE NO ANTIRETROVIRAL TREATMENT HISTORY OR TO REPLACE THE CURRENT ANTIRETROVIRAL REGIMEN IN THOSE WHO ARE VIROLOGICALLY-SUPPRESSED (HIV-1 RNA LESS THAN 50 COPIES PER ML) ON A STABLE ANTIRETROVIRAL REGIMEN WITH NO HISTORY OF TREATMENT FAILURE AND NO KNOWN SUBSTITUTIONS ASSOCIATED WITH RESISTANCE TO THE INDIVIDUAL COMPONENTS OF BIKTARVY
EQ 50MG BASE;200MG;EQ 25MG BASE	BIKTARVY	GILEAD SCIENCES INC	N210251	Feb. 7, 2018	RX	TABLET	ORAL	Feb. 7, 2023	NEW CHEMICAL ENTITY
EQ 50MG BASE;200MG;EQ 25MG BASE	BIKTARVY	GILEAD SCIENCES INC	N210251	Feb. 7, 2018	RX	TABLET	ORAL	Feb. 24, 2024	LABELING REVISIONS RELATED TO CLINICAL STUDIES
EQ 50MG BASE;200MG;EQ 25MG BASE	BIKTARVY	GILEAD SCIENCES INC	N210251	Feb. 7, 2018	RX	TABLET	ORAL	June 18, 2026	FOR HIV-1 INFECTION IN PEDIATRIC PTS AT LEAST 25 KG W/ NO ANTIRETROVIRAL (ARV) TX HX OR TO REPLACE CURRENT ARV REGIMEN FOR VIROLOGICALLY-SUPPRESSED ON STABLE ARV W/ NO HX TX FAILURE AND NO KNOWN SUBSTITUTIONS ASSOCIATED W/ RESISTANCE TO BIC, FTC, OR TAF

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Reverse transcriptase/RNaseH	Enzyme		Q72547_9HIV1	INHIBITOR				CHEMBL	CHEMBL

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External reference:

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ID	Source
ETV	PDB_CHEM_ID
001321	NDDF
11244	IUPHAR_LIGAND_ID
17421	MMSL
276237	RXNORM
338322	MMSL
4021395	VUID
4021395	VANDF
404855005	SNOMEDCT_US
404856006	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Atripla	HUMAN PRESCRIPTION DRUG LABEL	3	15584-0101	TABLET, FILM COATED	200 mg	ORAL	NDA	34 sections
Biktarvy	HUMAN PRESCRIPTION DRUG LABEL	3	50090-6247	TABLET	200 mg	ORAL	NDA	33 sections
Efavirenz, Emtricitabine and Tenofovir Disoproxil Fumarate	HUMAN PRESCRIPTION DRUG LABEL	3	0093-5234	TABLET, FILM COATED	200 mg	ORAL	ANDA	30 sections
Efavirenz, Emtricitabine and Tenofovir Disoproxil Fumarate	HUMAN PRESCRIPTION DRUG LABEL	3	0093-5234	TABLET, FILM COATED	200 mg	ORAL	ANDA	30 sections
Efavirenz, Emtricitabine and Tenofovir Disoproxil Fumarate	HUMAN PRESCRIPTION DRUG LABEL	3	31722-736	TABLET, FILM COATED	200 mg	ORAL	ANDA	28 sections
Efavirenz, Emtricitabine and Tenofovir Disoproxil Fumarate	Human Prescription Drug Label	3	33342-138	TABLET, FILM COATED	200 mg	ORAL	ANDA	30 sections
Efavirenz, emtricitabine and tenofovir disoproxil fumarate	Human Prescription Drug Label	3	42385-915	TABLET, FILM COATED	200 mg	ORAL	ANDA	30 sections
Emtricitabine and Tenofovir Disoproxil Fumarate	HUMAN PRESCRIPTION DRUG LABEL	2	0093-7607	TABLET, FILM COATED	200 mg	ORAL	ANDA	29 sections
Emtricitabine and Tenofovir Disoproxil Fumarate	HUMAN PRESCRIPTION DRUG LABEL	2	0093-7704	TABLET, FILM COATED	200 mg	ORAL	ANDA	29 sections
Emtricitabine and Tenofovir Disoproxil Fumarate	HUMAN PRESCRIPTION DRUG LABEL	2	0093-7704	TABLET, FILM COATED	200 mg	ORAL	ANDA	29 sections

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