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Also known as: 143491-57-0, Emtriva, Coviracil, (-)-ftc, 4-amino-5-fluoro-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1h)-one, 143491-54-7
Molecular Formula
C8H10FN3O3S
Molecular Weight
247.25  g/mol
InChI Key
XQSPYNMVSIKCOC-NTSWFWBYSA-N
FDA UNII
ULS8902U4O

Emtricitabine
A deoxycytidine analog and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B viruses. It is used to treat HIV INFECTIONS.
Emtricitabine is a Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of emtricitabine is as a Nucleoside Reverse Transcriptase Inhibitor.
1 2D Structure

Emtricitabine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
2.1.2 InChI
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
2.1.3 InChI Key
XQSPYNMVSIKCOC-NTSWFWBYSA-N
2.1.4 Canonical SMILES
C1C(OC(S1)CO)N2C=C(C(=NC2=O)N)F
2.1.5 Isomeric SMILES
C1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F
2.2 Other Identifiers
2.2.1 UNII
ULS8902U4O
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Beta L 2',3' Dideoxy 5 Fluoro 3' Thiacytidine

2. Beta-l-2',3'-dideoxy-5-fluoro-3'-thiacytidine

3. Coviracil

4. Emtriva

2.3.2 Depositor-Supplied Synonyms

1. 143491-57-0

2. Emtriva

3. Coviracil

4. (-)-ftc

5. 4-amino-5-fluoro-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1h)-one

6. 143491-54-7

7. 524w91

8. Bw-524w91

9. Ftc

10. Racivir

11. 4-amino-5-fluoro-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one

12. Bw524w91

13. (-)-2'-deoxy-5-fluoro-3'-thiacytidine

14. Ftc-(-)

15. Bw 524w91

16. (-)-emtricitabine

17. (2r-cis)-4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1h)-pyrimidinone

18. (-)-beta-2',3'-dideoxy-5-fluoro-3'-thiacytidine

19. Chebi:31536

20. 5-fluoro-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine

21. Emtricitabine, (-)-

22. Psi-5004

23. 4-amino-5-fluoro-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1h)-one

24. 145213-48-5

25. G70b4etf4s

26. Uls8902u4o

27. Emtritabine

28. Bw1592

29. (-)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1h)-pyrimidin-2-one

30. 2',3'-dideoxy-5-fluoro-3'-thiacytidine

31. Ncgc00164564-01

32. (-)-(2r,5s)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine

33. 2(1h)-pyrimidinone, 4-amino-5-fluoro-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, Rel-

34. 524-w-91

35. Psi 5004

36. Mfcd00870151

37. Ftc, Dl-

38. Coviracil(tm)

39. Drg-0208

40. 4-amino-5-fluoro-1-((2r,5s)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-1h-pyrimidin-2-one

41. Rel-4-amino-5-fluoro-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1h)-pyrimidinone

42. Emtriva(tm)

43. 2(1h)-pyrimidinone, 4-amino-5-fluoro-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, Rel-

44. Emtricitabine (emtriva)

45. Smr002533604

46. Bw 1592

47. 2',3',5-ftc

48. Emtricitabine, (+/-)-

49. Hsdb 7337

50. 4-amino-5-fluoro-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

51. Ftc, (-)-

52. Unii-g70b4etf4s

53. Emtricitabine [usan:inn]

54. (-)-.beta.-l-ftc

55. Unii-uls8902u4o

56. Emtricitabinum

57. (+/-)-ftc

58. 2(1h)-pyrimidinone,4-amino-5-fluoro-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-

59. 2(1h)-pyrimidinone,4-amino-5-fluoro-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-

60. Emtricitabine- Bio-x

61. Emtricitabine [mi]

62. Chembl885

63. Emtricitabine [inn]

64. Emtricitabine [jan]

65. 2(1h)-pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, Cis-

66. Dsstox_cid_20129

67. Dsstox_rid_79445

68. Emtricitabine [hsdb]

69. Emtricitabine [usan]

70. Dsstox_gsid_40129

71. Schembl39708

72. Emtricitabine [vandf]

73. Mls003882429

74. Mls006011556

75. Mls006011987

76. Emtricitabine [mart.]

77. Emtricitabine [usp-rs]

78. Emtricitabine [who-dd]

79. Emtricitabine [who-ip]

80. Dtxsid0040129

81. Emtricitabine [ema Epar]

82. Gtpl11244

83. Ex-a150

84. Hms2089i05

85. Hms3713l12

86. Emtricitabine [orange Book]

87. Zinc3629271

88. Tox21_112193

89. ((-))-ftc

90. Bdbm50107843

91. Cs1125

92. Ftc-((-))

93. Nsc804863

94. S1704

95. Atripla Component Emtricitabine

96. Descovy Component Emtricitabine

97. Emtricitabinum [who-ip Latin]

98. Odefsey Component Emtricitabine

99. Truvada Component Emtricitabine

100. Akos015853098

101. Akos015894950

102. Eviplera Component Emtricitabine

103. Stribild Component Emtricitabine

104. Am84393

105. Ccg-220615

106. Cs-1370

107. Db00879

108. Nsc-804863

109. 2',3'-dideoxy-3-thia-5-fluorocytidine

110. Descovy Component Of Emtricitabine

111. Emtricitabine Component Of Atripla

112. Emtricitabine Component Of Descovy

113. Emtricitabine Component Of Genvoya

114. Emtricitabine Component Of Odefsey

115. Emtricitabine Component Of Truvada

116. Ncgc00164564-06

117. Ncgc00164564-09

118. Ncgc00164564-10

119. 2(1h)-pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2r-cis)-

120. 2(1h)-pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, Cis-(+-)-

121. As-14099

122. Be165946

123. Emtricitabine Component Of Eviplera

124. Emtricitabine Component Of Stribild

125. Hy-17427

126. Cas-143491-57-0

127. E1007

128. Emtricitabine 100 Microg/ml In Acetonitrile

129. Sw220172-1

130. D01199

131. D72669

132. Ent-emtricitabine; Emtricitabine Ip Impurity D

133. Ab01275429-01

134. 491e570

135. Q422604

136. W-201247

137. W-201248

138. 2',3'-dideoxy-5-fluoro-3'-thiacytidine, Dl-

139. Z1739256297

140. .beta.-l-(-)-(2r,5s)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine

141. 5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine (2r,5s)

142. 2(1h)-pyrimidinone, 4-amino-5-fluoro-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-

143. 4-amino-5-fluoro-1-[(2s,5r)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1h)-pyrimidinone; (+)-2'-deoxy-3'-thia-5-fluorocytidine; (2s-cis)-4-amino-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1h)-pyrimidinone

144. 5-fluoro-(-)-l-2',3'-dideoxy-3'-thiacytidine; (-)-beta-2',3'-dideoxy-5-fluoro-3'-thiacytidine; Emtricitabine; Emtriva

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 247.25 g/mol
Molecular Formula C8H10FN3O3S
XLogP3-0.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass247.04269053 g/mol
Monoisotopic Mass247.04269053 g/mol
Topological Polar Surface Area113 Ų
Heavy Atom Count16
Formal Charge0
Complexity374
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameEmtricitabine
PubMed HealthEmtricitabine (By mouth)
Drug ClassesAntiretroviral Agent
Drug LabelEMTRIVA is the brand name of emtricitabine, a synthetic nucleoside analog with activity against human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.The chemical name of emtricitabine is 5-fluoro-1-(2R,5S)-[2-(hydroxymethyl)-1,3-oxathiol...
Active IngredientEmtricitabine
Dosage FormCapsule
Routeoral
Strength200mg
Market StatusTentative Approval
CompanyMatrix Labs; Aurobindo Pharma; Cipla

2 of 4  
Drug NameEmtriva
PubMed HealthEmtricitabine (By mouth)
Drug ClassesAntiretroviral Agent
Drug LabelEMTRIVA is the brand name of emtricitabine, a synthetic nucleoside analog with activity against human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.The chemical name of emtricitabine is 5-fluoro-1-(2R,5S)-[2-(hydroxymethyl)-1,3-oxathiol...
Active IngredientEmtricitabine
Dosage FormCapsule; Solution
Routeoral; Oral
Strength200mg; 10mg/ml
Market StatusPrescription
CompanyGilead

3 of 4  
Drug NameEmtricitabine
PubMed HealthEmtricitabine (By mouth)
Drug ClassesAntiretroviral Agent
Drug LabelEMTRIVA is the brand name of emtricitabine, a synthetic nucleoside analog with activity against human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.The chemical name of emtricitabine is 5-fluoro-1-(2R,5S)-[2-(hydroxymethyl)-1,3-oxathiol...
Active IngredientEmtricitabine
Dosage FormCapsule
Routeoral
Strength200mg
Market StatusTentative Approval
CompanyMatrix Labs; Aurobindo Pharma; Cipla

4 of 4  
Drug NameEmtriva
PubMed HealthEmtricitabine (By mouth)
Drug ClassesAntiretroviral Agent
Drug LabelEMTRIVA is the brand name of emtricitabine, a synthetic nucleoside analog with activity against human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.The chemical name of emtricitabine is 5-fluoro-1-(2R,5S)-[2-(hydroxymethyl)-1,3-oxathiol...
Active IngredientEmtricitabine
Dosage FormCapsule; Solution
Routeoral; Oral
Strength200mg; 10mg/ml
Market StatusPrescription
CompanyGilead

4.2 Therapeutic Uses

Antiviral Agents

National Library of Medicine's Medical Subject Headings. Emtricitabine. Online file (MeSH, 2014). Available from, as of November 19, 2013: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html


Emtricitabine is used in conjunction with other antiretroviral agents for the treatment of HIV-1 infection in pediatric patients 12 years of age or older. The fixed combination containing emtricitabine and tenofovir (Truvada) can be used in conjunction with other antiretrovirals in children 12 years of age or older weighing at least 35 kg. For initial treatment of HIV-infected pediatric patients, the HHS Panel on Antiretroviral Therapy and Medical Management of HIV-infected Children recommends antiretroviral therapy with at least 3 drugs, including either a PI or NNRTI with 2 NRTIs. When PI-based or NNRTI-based regimens are used in pediatric patients, emtricitabine and (abacavir (for individuals 3 months of age or older who test negative for the HLA-B*5701 allele), tenofovir (for adolescents 12 years of age or older at Tanner stage 4 or 5), or zidovudine) are preferred dual NRTI options. A dual NRTI combination of emtricitabine and lamivudine is not recommended, because of similar resistance profiles and minimal additive antiretroviral activity. A triple NRTI regimen that includes abacavir, tenofovir, and either lamivudine or emtricitabine or a triple NRTI regimen that includes tenofovir, didanosine, and either lamivudine or emtricitabine should not be used at any time in pediatric patients because of the high rate of early virologic failure reported in antiretroviral-naive adults.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 700


Emtricitabine has been evaluated in a randomized, open-label, multicenter study (study 303) in 440 previously treated adults (mean age: 42 years; 86% male; 64% white; 13% Hispanic; 21% African American; median baseline plasma HIV-1 RNA level: 1.7 log10 copies/mL; mean baseline CD4+ T-cell count: 527 cells/mm3) who had received a lamivudine-containing regimen that also included 2 other antiretrovirals (background regimen) for at least 12 weeks prior to study entry and had plasma HIV-1 levels of 400 copies/mL or less. Patients in this study were randomized to receive emtricitabine in conjunction with stavudine or zidovudine and PI or NNRTI or to continue their lamivudine-containing background regimen (i.e., lamivudine in conjunction with stavudine or zidovudine and a PI or NNRTI). At week 48, 77 and 67% of adults receiving the regimen that included emtricitabine and 82 and 72% of those receiving the regimen that included lamivudine had plasma HIV-1 RNA levels less than 400 or 50 copies/mL, respectively. Virologic failure (i.e., individuals who failed to achieve virologic suppression or experienced rebound after achieving virologic suppression) was reported in 7% of those receiving the emtricitabine-containing regimen and in 8% of those receiving the lamivudine-containing regimen at week 48. Administration of the emtricitabine-containing regimen resulted in a mean increase in CD4+ T-cell counts of 29 cells/mm3; administration of the lamivudine-containing regimen resulted in a mean increase in CD4+ T-cell counts of 61 cells/cu mm.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 700


Safety and efficacy of emtricitabine used in conjunction with other antiretrovirals have been evaluated in a randomized multicenter study in treatment-naive adults (study 301A). In this study, 571 HIV-infected adults (mean age: 36 years; 85% male; 52% white; 26% Hispanic; 16% African American; median baseline plasma HIV-1 RNA level: 4.9 log10 copies/mL; mean baseline CD4+ T-cell count: 318 cells/mm3) were randomized to receive emtricitabine or stavudine in conjunction with didanosine (delayed-release capsules) and efavirenz. Results of this study indicated that an initial regimen that includes emtricitabine in conjunction with didanosine and efavirenz is as effective as an initial regimen of stavudine in conjunction with didanosine and efavirenz. At week 48, 81 and 78% of adults receiving the regimen that included emtricitabine and 68 and 59% of those receiving the regimen that included stavudine had plasma HIV-1 RNA levels less than 400 or 50 copies/mL, respectively. Virologic failure (i.e., individuals who failed to achieve virologic suppression or experienced rebound after achieving virologic suppression) at week 48 was reported in 3% of those receiving the emtricitabine-containing regimen and in 11% of those receiving the stavudine-containing regimen. At week 48, increases in CD4+ T-cell counts were greater in patients receiving the regimen that included emtricitabine (mean increase of 168 cells/mm3) than in those receiving the regimen that included stavudine (mean increase of 134 cells/mm3).

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 700


For more Therapeutic Uses (Complete) data for EMTRICITABINE (7 total), please visit the HSDB record page.


4.3 Drug Warning

Safety and efficacy of emtricitabine have been established for treatment of HIV-1 infection in children 3 months of age and older. The pharmacokinetics and safety of emtricitabine were evaluated in a dose-finding study in 20 neonates born to HIV-infected mothers.20 1 These neonates received zidovudine prophylaxis for 6 weeks. In addition, these neonates received 2 short courses of emtricitabine (3 mg/kg daily for 4 days per course) during the first 12 weeks of life. This dose was well tolerated and was not associated with any safety issues. Systemic exposure (area under the plasma concentration-time curve [AUC]) in infants 0-3 months of age receiving emtricitabine 3 mg/kg daily was similar to that reported in children 3 months to 17 years of age receiving emtricitabine 6 mg/kg daily. All neonates were HIV-1 negative at the end of the study (6 months postpartum); efficacy of emtricitabine for the prevention or treatment of HIV was not determined.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 703


Lactic acidosis and severe hepatomegaly with steatosis, including fatalities, have been reported in patients receiving nucleoside reverse transcriptase inhibitors (NRTIs), including emtricitabine, in conjunction with other antiretroviral agents. Most reported cases have involved women; obesity and long-term therapy with a nucleoside analog also may be risk factors.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 702


Caution should be observed when nucleoside reverse transcriptase inhibitors are used in patients with known risk factors for liver disease; however, lactic acidosis and severe hepatomegaly with steatosis have been reported in patients with no known risk factors. Emtricitabine therapy should be interrupted in any patient with clinical or laboratory findings suggestive of lactic acidosis or pronounced hepatotoxicity (signs of hepatotoxicity include hepatomegaly and steatosis even in the absence of marked increases in serum aminotransferase concentrations).

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 702


Prior to initiation of emtricitabine therapy for the treatment of HIV-1 infection, patients should be tested for chronic hepatitis B virus (HBV). Emtricitabine is not indicated for the treatment of chronic HBV infection; safety and efficacy of the drug have not been established in patients with coexisting HBV and HIV infections. Exacerbations of HBV infection have been reported in HIV-infected patients following discontinuance of emtricitabine. Patients with HBV infection and HIV infection should be closely monitored with clinical and laboratory follow-up for at least several months after stopping emtricitabine therapy.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 702


For more Drug Warnings (Complete) data for EMTRICITABINE (13 total), please visit the HSDB record page.


4.4 Drug Indication

Emtricitabine is indicated in combination with other medications for the treatment of HIV-1 infections; treatment of HIV-1 infections in pediatric patients 25-35kg, treatment of HIV-1 infections in adult patients 35kg, for pre exposure prophylaxis of HIV-1 in adolescent and adult patients excluding those who have receptive vaginal sex; treatment of HIV-1 infections in pediatric and adult patients 17kg, pre exposure prophylaxis in adolescents and adults 35kg; treatment of HIV-1 in patients 12 years and 35kg; treatment of HIV-1 in patients weighing 35kg; treatment of HIV-1 in patients weighing 25kg; and treatment of HIV-1 in patients weighing 40kg.


FDA Label


Emtriva is indicated for the treatment of HIV-1 infected adults and children in combination with other antiretroviral agents.

This indication is based on studies in treatment-naive patients and treatment-experienced patients with stable virological control. There is no experience of the use of Emtriva in patients who are failing their current regimen or who have failed multiple regimens.

When deciding on a new regimen for patients who have failed an antiretroviral regimen, careful consideration should be given to the patterns of mutations associated with different medicinal products and the treatment history of the individual patient. Where available, resistance testing may be appropriate.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Emtricitabine is a cytidine analog that competes with the natural substrate of HIV-1 reverse transcriptase to be incorporated into newly formed DNA, terminating its transcription. It is administered once daily so it has a long duration of action. Patients should be counselled regarding the risk of lactic acidosis and hepatomegaly with steatosis.


5.2 MeSH Pharmacological Classification

Anti-HIV Agents

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)


Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)


Reverse Transcriptase Inhibitors

Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
EMTRICITABINE
5.3.2 FDA UNII
G70B4ETF4S
5.3.3 Pharmacological Classes
Nucleoside Reverse Transcriptase Inhibitors [MoA]; Nucleosides [CS]; Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]
5.4 ATC Code

J05AF09


J05AF09

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors

J05AF09 - Emtricitabine


5.5 Absorption, Distribution and Excretion

Absorption

Emtricitabine reaches a Cmax of 1.80.7g/mL with a Tmax of 1-2 hours, and has an AUC of 103.1g\*hr/mL. The bioavailability of emtricitabine capsules is 93% and the bioavailability of the oral solution is 75%. Taking emtricitabine with food decreases the Cmax by 29%.[L9019


Route of Elimination

Emtricitabine is 86% recovered in the urine and 14% recovered in feces. 13% of the dose is recovered in the urine as metabolites; 9% as 3'-sulfoxide diastereomers and 4% as 2'-O-glucuronide.


Volume of Distribution

The apparent central volume of distribution is 42.3L and the peripheral volume of distribution is 55.4L.


Clearance

Emtricitabine has an apparent elimination rate of 15.1L/h. This rate is closely linked to creatinine clearance.


Emtricitabine is rapidly and extensively absorbed following oral administration with peak plasma concentrations occurring at 1 to 2 hours post-dose. Following multiple dose oral administration of emtriva to 20 HIV-infected subjects, the (mean + or - SD) steady state plasma emtricitabine peak concentration (Cmax) was 1.8 + or 0.7 ug/mL and the area under the plasma concentration-time curve over a 24-hour dosing interval (AUC) was 10.0 + or - 3.1 hr/ug/mL. The mean steady state plasma trough concentration at 24 hours post-dose was 0.09 ug/mL. The mean absolute bioavailability of emtriva was 93%.

Physicians Desk Reference 65th ed. PDR Network, LLC, Montvale, NJ. 2011, p. 1154


In vitro binding of emtricitabine to human plasma proteins was <4% and independent of concentration over the range of 0.02 to 200 ug/mL. At peak plasma concentration, the mean plasma to blood drug concentration ratio was approximately 1.0 and the mean semen to plasma drug concentration ratio was approximately 4.0.

Physicians Desk Reference 65th ed. PDR Network, LLC, Montvale, NJ. 2011, p. 1155


Time to peak concentration: 1 to 2 hours post dose

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 1265


Emtricitabine is distributed into human milk in low concentrations.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 703


For more Absorption, Distribution and Excretion (Complete) data for EMTRICITABINE (6 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Emtricitabine is approximately 86% unmetabolized. Approximately 9% of a dose is metabolized to 3'-sulfoxide diastereomers, 4% to the 2'-O-glucuronide, and a minor amount is converted to 5-fluorocytosine.


The biotransformation of emtricitabine includes oxidation of the thiol moiety to form the 3'-sulfoxide diastereomers (approximately 9% of dose) and conjugation with glucuronic acid to form 2'-O-glucuronide (approximately 4% of dose). No other metabolites were identifiable. Emtricitabine is not metabolized by liver enzymes.

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 1265


5.7 Biological Half-Life

The half life of emtricitabine is approximately 10 hours.


The plasma emtricitabine half-life is approximately 10 hours.

Physicians Desk Reference 65th ed. PDR Network, LLC, Montvale, NJ. 2011, p. 1155


5.8 Mechanism of Action

Emtricitabine is a cytidine analog which, when phosphorylated to emtricitabine 5'-triphosphate, competes with deoxycytidine 5'-triphosphate for HIV-1 reverse transcriptase. As HIV-1 reverse transcriptase incorporates emtricitabine into forming DNA strands, new nucleotides are unable to be incorporated, leading to viral DNA chain termination. Inhibition of reverse transcriptase prevents transcription of viral RNA into DNA, therefore the virus is unable to incorporate its DNA into host DNA and replicate using host cell machinery. This reduces viral load.


Emtricitabine, a synthetic nucleoside analog of cytosine, 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. Emtricitabine 5'-triphosphate is a weak inhibitor of mammalian DNA polymerase alpha, beta, epsilon and mitochondrial DNA polymerase gamma.

Physicians Desk Reference 65th ed. PDR Network, LLC, Montvale, NJ. 2011, p. 1155


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Rev. Date : 2017-12-01

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DMF Number : 20708

Submission : 2007-07-18

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Cipla Ltd

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12-Jan-2021
21-Aug-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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DOSAGE - TABLET;ORAL - 200MG;EQ 25MG BASE;300...DOSAGE - TABLET;ORAL - 200MG;EQ 25MG BASE;300MG

USFDA APPLICATION NUMBER - 202123

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DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;300M...DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;300MG

USFDA APPLICATION NUMBER - 203100

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DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;EQ 1...DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;EQ 10MG BASE

USFDA APPLICATION NUMBER - 207561

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DOSAGE - TABLET;ORAL - 120MG;EQ 15MG BASE

USFDA APPLICATION NUMBER - 208215

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DOSAGE - TABLET;ORAL - 200MG;EQ 25MG BASE

USFDA APPLICATION NUMBER - 208215

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DOSAGE - TABLET;ORAL - 200MG;EQ 25MG BASE;EQ ...DOSAGE - TABLET;ORAL - 200MG;EQ 25MG BASE;EQ 25MG BASE

USFDA APPLICATION NUMBER - 208351

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DOSAGE - TABLET;ORAL - EQ 30MG BASE;120MG;EQ ...DOSAGE - TABLET;ORAL - EQ 30MG BASE;120MG;EQ 15MG BASE

USFDA APPLICATION NUMBER - 210251

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DOSAGE - TABLET;ORAL - EQ 50MG BASE;200MG;EQ ...DOSAGE - TABLET;ORAL - EQ 50MG BASE;200MG;EQ 25MG BASE

USFDA APPLICATION NUMBER - 210251

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DOSAGE - CAPSULE;ORAL - 200MG

USFDA APPLICATION NUMBER - 21500

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DOSAGE - TABLET;ORAL - 100MG;150MG

USFDA APPLICATION NUMBER - 21752

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DOSAGE - TABLET;ORAL - 133MG;200MG

USFDA APPLICATION NUMBER - 21752

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DOSAGE - TABLET;ORAL - 167MG;250MG

USFDA APPLICATION NUMBER - 21752

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DOSAGE - TABLET;ORAL - 200MG;300MG

USFDA APPLICATION NUMBER - 21752

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