EMTRICITABINE, (±)-

Details

Stereochemistry	RACEMIC
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

Molecular Formula	C8H10FN3O3S
Molecular Weight	247.247
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 67 Target ID: CHEMBL247 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	Inhibitor 8297		0.31 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 151 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021500s010,021896s004lbl.pdf	Primary		Approved 8429	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 2003

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 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2B6 810 CYP2C19 1478 CYP2E1 882 CYP3A4/5 278 UGT 35	MATE1 135 OCT1 327 OCT2 355 P-gp 1537 BCRP 561 MRP2 205

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
CYP3A4/5 335	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-500_Emtriva_BioPharmr_P1.pdf#page=16 Page: 16.0	no
UGT 59	inhibitor 3277 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 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
MRP2 205	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
OCT1 327	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
OCT2 355	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27052107/	no
MATE1 135	substrate 3367 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
Perspectives for the treatment of hepatitis B virus infections.	1999 Jul	10418752
Highlights in the development of new antiviral agents.	2002 Apr	12370077
Treatment of chronic hepatitis B: case selection and duration of therapy.	2002 Apr	11982721
Management of patients with chronic hepatitis B.	2002 Apr	11982720
Management of viral hepatitis B.	2002 Feb	12000599
[New management strategies for hepatitis B].	2002 Feb	11938061
Chronic hepatitis B: current and future treatment options.	2002 Jun	12066963
Dose range study of pharmacokinetics, safety, and preliminary antiviral activity of emtricitabine in adults with hepatitis B virus infection.	2002 Jun	12019083
Gateways to clinical trials.	2002 Nov	12616707
New anti-HIV agents and targets.	2002 Nov	12369088
Emtricitabine: an antiretroviral agent for HIV infection.	2003	14609348
US FDA approves Emtriva (FTC).	2003 Aug	14669738
Selection of a hepatitis B virus strain resistant to adefovir in a liver transplantation patient.	2003 Dec	14642631
Prospective randomized trial of emtricitabine versus lamivudine short-term monotherapy in human immunodeficiency virus-infected patients.	2003 Dec 1	14639535
FTC (Emtriva) approved.	2003 Jul 25	14679924
Gateways to clinical trials.	2003 Jun	12851663
Gateways to clinical trials. March 2003.	2003 Mar	12731460
Current and future antiviral agents for chronic hepatitis B.	2003 Mar	12615847
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
FDA notifications. NRTI Emtriva receives FDA approval.	2003 Oct	14686301
Gateways to clinical trials.	2003 Oct	14671684
Emtricitabine/tenofovir disoproxil fumarate.	2004	15341498
Biochemical and mechanistic basis for the activity of nucleoside analogue inhibitors of HIV reverse transcriptase.	2004	15193137
[Approval of a new nucleoside. Component of complete once daily regimen].	2004 Apr 26	15373067
[Improved long-term success. New nucleoside for once daily combinations].	2004 Apr 26	15373043
Emtricitabine: a new nucleoside analogue for once-daily antiretroviral therapy.	2004 Jan	14680453
Gateways to clinical trials.	2004 Jun	15319815
Antiviral drugs in current clinical use.	2004 Jun	15125867
Initial therapy for human immunodeficiency virus: broadening the options.	2004 Mar-Apr	15116286
Emtricitabine (FTC) for the treatment of HIV infection.	2004 May	15206508
Pharmacokinetic and pharmacodynamic characteristics of emtricitabine support its once daily dosing for the treatment of HIV infection.	2004 Nov	15588339
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

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)

Substance Class	Chemical Created by `admin` on `Sat Dec 16 06:50:02 GMT 2023` Edited by `admin` on `Sat Dec 16 06:50:02 GMT 2023`
Record UNII	ULS8902U4O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EMTRICITABINE, (±)-

Common Name

English

(±)-FTC

Common Name

English

PSI-5004

Code

English

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

Common Name

English

FTC, DL-

Common Name

English

2',3'-DIDEOXY-5-FLUORO-3'-THIACYTIDINE, DL-

Common Name

English

Code System Code Type Description

DRUG BANK

DB12753