MITOTOX

Drug

D0046 | Emtricitabine

Properties

Molecular Formula	C8H10FN3O3S
Molecular Weight	247.25
Structure
State	solid
Clearance	* 302 +/- 94 mL/min [Renal Function Creatinine Clearance>80 ml/min] * 168 +/- 10 mL/min [Renal Function Creatinine Clearance 50-80 ml/min] * 138 +/- 28 mL/min [Renal Function Creatinine Clearance 30-49 ml/min] * 99 +/- 6 mL/min [Renal Function Creatinine Clearance<30 ml/min] * 64 +/- 12 mL/min [ESRD patients requiring dialysis]
Route of elimination	The renal clearance of emtricitabine is greater than the estimated creatinine clearance, suggesting elimination by both glomerular filtration and active tubular secretion.
Protein binding	Very low (less than 4%)
Half life	10 hours
Absorption	Rapidly absorbed (mean absolute bioavailability of 93% for capsules, and 75% for solution). Food does not effect absorption.
Trade names	Emtriva (formerly Coviracil),
Description	nucleoside reverse transcriptase inhibitor (NRTI)

Therapeutic Classification Source: DrugBank

J

J05AR22 Emtricitabine, tenofovir alafenamide, darunavir and cobicistat

[J05AR] Antivirals for treatment of HIV infections, combinations

[J05A] DIRECT ACTING ANTIVIRALS

[J05] ANTIVIRALS FOR SYSTEMIC USE

[J] Antiinfectives for systemic use

J05AR20 Emtricitabine, tenofovir alafenamide and bictegravir

[J05AR] Antivirals for treatment of HIV infections, combinations

[J05A] DIRECT ACTING ANTIVIRALS

[J05] ANTIVIRALS FOR SYSTEMIC USE

[J] Antiinfectives for systemic use

J05AR19 Emtricitabine, tenofovir alafenamide and rilpivirine

[J05AR] Antivirals for treatment of HIV infections, combinations

[J05A] DIRECT ACTING ANTIVIRALS

[J05] ANTIVIRALS FOR SYSTEMIC USE

[J] Antiinfectives for systemic use

J05AR18 Emtricitabine, tenofovir alafenamide, elvitegravir and cobicistat

[J05AR] Antivirals for treatment of HIV infections, combinations

[J05A] DIRECT ACTING ANTIVIRALS

[J05] ANTIVIRALS FOR SYSTEMIC USE

[J] Antiinfectives for systemic use

J05AR17 Emtricitabine and tenofovir alafenamide

[J05AR] Antivirals for treatment of HIV infections, combinations

[J05A] DIRECT ACTING ANTIVIRALS

[J05] ANTIVIRALS FOR SYSTEMIC USE

[J] Antiinfectives for systemic use

J05AR09 Emtricitabine, tenofovir disoproxil, elvitegravir and cobicistat

[J05AR] Antivirals for treatment of HIV infections, combinations

[J05A] DIRECT ACTING ANTIVIRALS

[J05] ANTIVIRALS FOR SYSTEMIC USE

[J] Antiinfectives for systemic use

J05AR08 Emtricitabine, tenofovir disoproxil and rilpivirine

[J05AR] Antivirals for treatment of HIV infections, combinations

[J05A] DIRECT ACTING ANTIVIRALS

[J05] ANTIVIRALS FOR SYSTEMIC USE

[J] Antiinfectives for systemic use

J05AR06 Emtricitabine, tenofovir disoproxil and efavirenz

[J05AR] Antivirals for treatment of HIV infections, combinations

[J05A] DIRECT ACTING ANTIVIRALS

[J05] ANTIVIRALS FOR SYSTEMIC USE

[J] Antiinfectives for systemic use

J05AR03 Tenofovir disoproxil and emtricitabine

[J05AR] Antivirals for treatment of HIV infections, combinations

[J05A] DIRECT ACTING ANTIVIRALS

[J05] ANTIVIRALS FOR SYSTEMIC USE

[J] Antiinfectives for systemic use

J05AF09 Emtricitabine

[J05AF] Nucleoside and nucleotide reverse transcriptase inhibitors

[J05A] DIRECT ACTING ANTIVIRALS

[J05] ANTIVIRALS FOR SYSTEMIC USE

[J] Antiinfectives for systemic use

Mitochondrial Toxicity Evaulation

Toxicity	Dose	Time	Species	Model	Method	Action	Positive criterion	Reference
MITOCHONDRIAL DNA METABOLIC PROCESS								194

Targets

Target	Dose	Time	Species	Model	Method	Action	Positive criterion	Reference
DNA polymerase gamma								194

Indications Source: SIDER

Alcohol abuse

Alcoholism

Blood bilirubin increased

HIV infection

Imprisonment

Infection

Renal failure

Renal impairment

Sexually transmitted disease

Viral infection

Side effects Source: SIDER

Abdominal pain (0.1)

Upper respiratory tract infection (0.05)

Anaemia

Dermatitis

Diarrhoea

Fasting

Haematuria

Headache

Hyperglycaemia

Nausea

Rash

Vomiting

Synonyms Source: PubChem

((-))-FTC	(+)-2'-Deoxy-3'-thia-5-fluorocytidine	(-)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
(-)-.beta.-L-FTC	(-)-2'-Deoxy-5-fluoro-3'-thiacytidine	(-)-BETA-2',3'-DIDEOXY-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	(2S-cis)-4-Amino-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone	.beta.-L-(-)-(2R,5S)-5-Fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
1-(2-(Hydroxymethyl)oxathiolan-5-yl)-5-fluorocytosine	143491-54-7	143491-57-0
145213-48-5	2',3',5-FTC	2',3'-Dideoxy-3-thia-5-fluorocytidine
2',3'-Dideoxy-5-fluoro-3'-thiacytidine	2'-Deoxy-5-fluoro-3'-oxa-4'-thiocytidine	2'-Deoxy-5-fluoro-3'-thiacytidine
2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, rel-	2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2R-cis)-	2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, cis-
2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, cis-(+-)-	2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, rel-	2(1H)-Pyrimidinone,4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-
2-FTC	24229-EP2298783A1	24229-EP2314590A1
3'-Thia-2'.3'-dideoxy-5-fluorocytidine	4-Amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-1H-pyrimidin-2-one	4-Amino-5-fluoro-1-((2R,5S)-rel-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one
4-Amino-5-fluoro-1-((2S,5R)-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]-2-(1H-pyrimidinone	4-Amino-5-fluoro-1-[(2S,5R)-2-(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]-1,2-dihydropyrimidin-2-one	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	491E570	5-FLUORO-(-)-L-2',3'-DIDEOXY-3'-THIACYTIDINE
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	AB01275429-01	ABP001074
AKOS015853098	AKOS015894950	AM84393
ANW-58684	AS-14099	BDBM50107843
BW 1592	BW 524W91	BW-524W91
BW1592	BW524W91	C12599
C8H10FN3O3S	CAS-143491-57-0	CCG-220615
CE0036	CHEBI:31536	CHEMBL885
CS-1370	CTK4C4432	Coviracil
Coviracil(TM)	D01199	DB00879
DRG-0208	DSSTox_CID_20129	DSSTox_GSID_40129
DSSTox_RID_79445	DTXSID0040129	E1007
EMTRICITABINE	EMTRIVA	EX-A150
Emtricitabin	Emtricitabina	Emtricitabine
Emtricitabine IP Impurity D	Emtricitabine [USAN:INN]	Emtricitabinum
Emtritabine	Emtriva	Emtriva(TM)
FT-0080009	FT-0601789	FTC
FTC, (-)-	FTC-((-))	FTC-(-)
G70B4ETF4S	HMS2089I05	HMS3713L12
HSDB 7337	HY-17427	KS-00000L28
KS-00001CJ2	LS-135838	LS-173184
MCULE-7141046266	MFCD00870151	MLS003882429
MLS006011556	MLS006011987	NCGC00164564-01
NE44626	PSI 5004	PSI-5004
Q422604	RCV	RTC-020120
Racivir	SB18984	SC-17032
SCHEMBL39708	SMR002533604	ST2405540
SW220172-1	TC-020120	Tox21_112193
UNII-G70B4ETF4S	UNII-ULS8902U4O component XQSPYNMVSIKCOC-NTSWFWBYSA-N	W-201247
W-201248	XQSPYNMVSIKCOC-NTSWFWBYSA-N	Z1739256297
ZINC3629271	dOTFC	ent-Emtricitabine
s1704

External IDs

DrugBank Name	Emtricitabine
DrugBank	DB00879
CAS Number	137530-41-7, 143491-54-7, 143491-57-0, 145213-48-5
PubChem Compound	60877
KEGG Compound ID	C12599
KEGG Drug	D01199
PubChem.Substance	46507606
ChEBI	31536
PharmGKB	PA10069
ChemSpider	54859
BindingDB	50107843.0
TTD	DAP001084
Wikipedia	Emtricitabine
HET	ETV
DPD	16516

References

1. Dykens et al. (2007)

2. Dykens et al. (2007)