EMTRICITABINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H10FN3O3S
Molecular Weight	247.247
Optical Activity	( - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=O)N(C=C1F)[C@@H]2CS[C@H](CO)O2

InChI

InChIKey=XQSPYNMVSIKCOC-NTSWFWBYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf
Curator's Comment: Description was created based on several sources, including: http://www.emory.edu/news/Releases/emtri/

Emtricitabine was discovered by Emory researchers Dr. Dennis C. Liotta, Dr. Raymond F. Schinazi and Dr. Woo-Baeg Choi and licensed to Triangle Pharmaceuticals by Emory University in 1996. Triangle was acquired by Gilead in 2003. Emtricitabine, marketed by Gilead as Emtriva, was first approved by the U.S. Food and Drug Administration in July 2003 for the treatment of HIV infection in combination with other antiretroviral agents. Emtricitabine, a synthetic nucleoside analog of cytidine, is phosphorylated by cellular enzymes to form emtricitabine 5'-triphosphate. Emtricitabine 5'-triphosphate inhibits the activity of the HIV-1 reverse transcriptase by competing with the natural substrate deoxycytidine 5'-triphosphate and by being incorporated into nascent viral DNA which results in chain termination.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 reverse transcriptase 47 Target ID: CHEMBL247 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	Inhibitor 8228		0.31 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 150 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	Primary		Approved 8360	EMTRIVA Approved Use EMTRIVA is indicated, in combination with other antiretroviral agents, for the treatment of HIV-1 infection. Additional important information regarding the use of EMTRIVA for the treatment of HIV-1 Infection: • EMTRIVA should not be coadministered with ATRIPLA™, TRUVADA®, or Lamivudine-containing products (see WARNINGS). • In treatment-experienced patients, the use of EMTRIVA should be guided by laboratory testing and treatment history (see MICROBIOLOGY). Launch Date 1.057104E12

C_max

Value	Dose	Co-administered	Analyte	Population
1.8 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2.7 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	5.6 mg/kg 1 times / day steady-state, oral dose: 5.6 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
10 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
12.6 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	5.6 mg/kg 1 times / day steady-state, oral dose: 5.6 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
10 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
8.2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	5.6 mg/kg 1 times / day steady-state, oral dose: 5.6 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
96% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		EMTRICITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Co-administed with:: dolutegravir(50 mg) tenofovir disoproxil fumarate(300 mg) Sources: https://pubmed.ncbi.nlm.nih.gov/30420123/	unhealthy, 26 - 42 years n = 717 Health Status: unhealthy Condition: HIV-1 Age Group: 26 - 42 years Sex: M+F Population Size: 717 Sources: https://pubmed.ncbi.nlm.nih.gov/30420123/	Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (grade 2-5, 8 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/30420123/

AEs

AE	Significance	Dose	Population
Headache	grade 2-5, 8 patients Disc. AE	200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Co-administed with:: dolutegravir(50 mg) tenofovir disoproxil fumarate(300 mg) Sources: https://pubmed.ncbi.nlm.nih.gov/30420123/	unhealthy, 26 - 42 years n = 717 Health Status: unhealthy Condition: HIV-1 Age Group: 26 - 42 years Sex: M+F Population Size: 717 Sources: https://pubmed.ncbi.nlm.nih.gov/30420123/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1752	inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2A6 704 CYP2B6 799 CYP2C19 1463 CYP2E1 876 CYP3A4/5 273 UGT 34	MATE1 132 OCT1 322 OCT2 348 P-gp 1527 BCRP 555 MRP2 201

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2A6 736	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2B6 985	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2E1 964	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP3A4/5 330	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
UGT 58	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21500_emtriva_lbl.pdf#page=5 Page: 5.0	no

Drug as victim

Target	Modality	Activity
BCRP 555	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
MRP2 201	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
OCT1 322	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
OCT2 348	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
P-gp 1527	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
MATE1 132	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31536	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31536
ChemicalBook	CB5266199	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5266199
MolPort	MolPort-003-986-424	https://www.molport.com/shop/molecule-link/MolPort-003-986-424
ZINC	ZINC000003629271	http://zinc15.docking.org/substances/ZINC000003629271
eMolecules	6719178	https://www.emolecules.com/cgi-bin/more?vid=6719178

PubMed

Title	Date	PubMed
Selective inhibition of human immunodeficiency viruses by racemates and enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine.	1992 Nov	1283296
Five new drugs enter the homestretch.	2002 Dec	12635598
Gateways to clinical trials.	2002 Dec	12616965
Gateways to clinical trials.	2002 Nov	12616707
Treatment of HBeAg negative chronic hepatitis B with new drugs (adefovir and others).	2003	14708699
Entecavir, FTC, L-FMAU, LdT and others.	2003	14708692
Emtricitabine: an antiretroviral agent for HIV infection.	2003	14609348
Treatment of chronic hepatitis B in 2002.	2003	12839213
Emtricitabine: 524W91, BW524W91, Coviracil, FTC.	2003	12568636
The continuing evolution of HIV therapy.	2003 Dec	14959692
Selection of a hepatitis B virus strain resistant to adefovir in a liver transplantation patient.	2003 Dec	14642631
Treatment of chronic hepatitis B in the human immunodeficiency virus-infected patient: present and future.	2003 Dec 15	14689351
Anti-HIV drug updates--three drugs on the near horizon.	2003 Jan	12647672
In vitro activity of potential anti-poxvirus agents.	2003 Jan	12615301
Gateways to clinical trials.	2003 Jan-Feb	12690708
Reproductive toxicology profile of emtricitabine in mice and rabbits.	2003 Jan-Feb	12507664
FTC (Emtriva) approved.	2003 Jul 25	14679924
Gateways to clinical trials.	2003 Jul-Aug	12949633
Gateways to clinical trials. March 2003.	2003 Mar	12731460
New antiretroviral drugs.	2003 Mar	12667250
Once-a-day highly active antiretroviral therapy: a systematic review.	2003 May 1	12715315
Atazanavir (Reyataz) and emtricitabine (Emtriva) for HIV infection.	2003 Nov 10	14603099
Polysaccharide-based chiral phase under polar organic mode of elution in the determination of the enantiomeric purity of emtricitabine an anti-HIV analogue nucleoside.	2003 Nov 24	14623583
Three new drugs approved by FDA.	2003 Nov-Dec	14696579
FTC (emtricitabine, Emtriva).	2003 Oct	14696567
FDA notifications. NRTI Emtriva receives FDA approval.	2003 Oct	14686301
Assessment of the relative potency of emtricitabine and lamivudine.	2003 Oct 1	14526216
Emtricitabine: a new treatment option for simplified antiretroviral therapy.	2003 Sep	14601555
Emtriva gets approval.	2003 Sep	14596254
Pharmacokinetics of antiretrovirals in pregnant women.	2004	15568888
Newer treatments for HIV in children.	2004 Feb	14758118
Labeling changes for tenofovir.	2004 Jan	15006195
Emtricitabine: a new nucleoside analogue for once-daily antiretroviral therapy.	2004 Jan	14680453
[Recent progress in anti-HIM-1 research].	2004 Jun	15449905
Gateways to clinical trials.	2004 Jun	15319815
Editorial comment: HIV and HBV coinfection--a coming-of-age in treatment strategies.	2004 Mar	15068001
Pharmacokinetics of emtricitabine, didanosine and efavirenz administered once-daily for the treatment of HIV-infected adults (pharmacokinetic substudy of the ANRS 091 trial).	2004 Mar	15012649
New drugs of 2003.	2004 Mar-Apr	15098851
Gateways to clinical trials.	2004 May	15319808
[New approaches in the treatment of hepatitis B].	2004 May 21	15160325
Pharmacokinetic and pharmacodynamic characteristics of emtricitabine support its once daily dosing for the treatment of HIV infection.	2004 Nov	15588339
Pharmacologic perspectives for once-daily antiretroviral therapy.	2004 Nov	15479772
A randomized study of emtricitabine and lamivudine in stably suppressed patients with HIV.	2004 Nov 19	15577539
Nevirapine and efavirenz elicit different changes in lipid profiles in antiretroviral-therapy-naive patients infected with HIV-1.	2004 Oct	15526045
Combinations of adefovir with nucleoside analogs produce additive antiviral effects against hepatitis B virus in vitro.	2004 Oct	15388423
New nucleoside reverse transcriptase inhibitors for the treatment of HIV infections.	2004 Oct	15351346
HIV-chemotherapy and -prophylaxis: new drugs, leads and approaches.	2004 Sep	15183346
Resistance issues with new nucleoside/nucleotide backbone options.	2004 Sep 1	15319668
Pharmacokinetic properties of nucleoside/nucleotide reverse transcriptase inhibitors.	2004 Sep 1	15319664
Intracellular pharmacology of emtricitabine and tenofovir.	2004 Sep 15	15472830

Patents

Sample Use Guides

In Vivo Use Guide

Emtriva® (emtricitabine) dosage. Adult Patients (18 years of age and older):one 200 mg capsule administered once daily orally (Capsules). 240 mg (24 mL) administered once daily orally (Oral Solution). Pediatric Patients (0–3 months of age): 3 mg/kg administered once daily orally (Oral Solution). Pediatric Patients (3 months through 17 years): 6 mg/kg up to a maximum of 240 mg (24 mL) administered once daily orally (Oral Solution), for children weighing more than 33 kg who can swallow an intact capsule, one 200 mg capsule administered once daily orally (Capsules).

Route of Administration: Oral

In Vitro Use Guide

emtricitabine EC50 0.99 μM (in vitro activity against HIV-2)

Name

Type

Language

EMTRICITABINE

Official Name

English

524W91

Code

English

EMTRICITABINE, (-)-

Common Name

English

STRIBILD COMPONENT EMTRICITABINE

Brand Name

English

EMTRICITABINE COMPONENT OF STRIBILD

Brand Name

English

EVIPLERA COMPONENT EMTRICITABINE

Brand Name

English

DESCOVY COMPONENT EMTRICITABINE

Common Name

English

5-FLUORO-1-(2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)CYTOSINE (2R,5S)

Common Name

English

EMTRICITABINE COMPONENT OF DESCOVY

Common Name

English

EMTRICITABINE COMPONENT OF TRUVADA

Brand Name

English

EMTRICITABINE [USP-RS]

Common Name

English

EMTRICITABINE COMPONENT OF GENVOYA

Brand Name

English

DESCOVY COMPONENT OF EMTRICITABINE

Common Name

English

TRUVADA COMPONENT EMTRICITABINE

Brand Name

English

2(1H)-PYRIMIDINONE, 4-AMINO-5-FLUORO-1-((2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)-

Systematic Name

English

EMTRIVA

Brand Name

English

ATRIPLA COMPONENT EMTRICITABINE

Common Name

English

(-)-EMTRICITABINE

Common Name

English

FTC

Common Name

English

ODEFSEY COMPONENT EMTRICITABINE

Brand Name

English

EMTRICITABINE [MART.]

Common Name

English

COVIRACIL

Brand Name

English

EMTRICITABINE [MI]

Common Name

English

Emtricitabine [WHO-DD]

Common Name

English

EMTRICITABINE [EMA EPAR]

Common Name

English

EMTRICITABINE COMPONENT OF ODEFSEY

Brand Name

English

EMTRICITABINE [VANDF]

Common Name

English

EMTRICITABINE [ORANGE BOOK]

Common Name

English

5-Fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine

Systematic Name

English

EMTRICITABINE COMPONENT OF EVIPLERA

Brand Name

English

EMTRICITABINE [JAN]

Common Name

English

524-W-91

Code

English

EMTRICITABINE [HSDB]

Common Name

English

EMTRICITABINE [USAN]

Common Name

English

FTC-(-)

Code

English

EMTRICITABINUM [WHO-IP LATIN]

Common Name

English

EMTRICITABINE COMPONENT OF ATRIPLA

Common Name

English

EMTRICITABINE [WHO-IP]

Common Name

English

(-)-FTC

Common Name

English

BW-524W91

Code

English

emtricitabine [INN]

Common Name

English

(2R-CIS)-4-AMINO-5-FLUORO-1-(2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL)-2(1H)-PYRIMIDINONE

Systematic Name

English

Classification Tree Code System Code

WHO-ESSENTIAL MEDICINES LIST

6.4.2.3 (FTC/TEN)