WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H317769
CAS#: 143491-57-0
Description: Emtricitabine is a nucleoside analogue which inhibits the reverse nucleoside transcriptase enzyme. Structurally this antiviral agent is similar to Lamivudine. This agent is effective at targeting HIV and HBV viruses since these viruses replicate in a reverse transcriptase manner. Studies indicate that the structure of Emtricitabine, specifically the unnatural β-L structural configuration produce greater antiviral effects in vitro on HIV and HBV than other antiviral agents.
Hodoodo Cat#: H317769
Name: Emtricitabine
CAS#: 143491-57-0
Chemical Formula: C8H10FN3O3S
Exact Mass: 247.04
Molecular Weight: 247.250
Elemental Analysis: C, 38.86; H, 4.08; F, 7.68; N, 17.00; O, 19.41; S, 12.97
Synonym: Emtricitabine; 2-FTC; 524W91; BW 1592; BW-1592; BW1592; BW 524W91; BW-524W91; BW524W91; Coviracil; dOTFC; DRG-0208; DRG 0208; DRG0208; Emtriva.
IUPAC/Chemical Name: 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
InChi Key: XQSPYNMVSIKCOC-NTSWFWBYSA-N
InChi Code: 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
SMILES Code: C1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI). |
| In vitro activity: | In view of Emtricitabine's clinical significance, a thorough review of the physical and pharmaceutical characteristics and details of the multiple analytical techniques used to test the drug in pharmaceutical and biological systems was conducted. The methods investigated include identification test, Spectroscopy, chromatography, electrochemicals, and Thermal. Beside the analytical profile, the degradation and stability of Emtricitabine, its pharmacology and pharmacokinetics, Pharmaceutical Applications, Mechanism of Action, dosage forms and dose, ADME profile, and interactions have been debated. Reference: Al-Majed AA, Bakheit AHH, Al-Qahtani BM, Al-Kahtani HM, Abdelhameed AS. Emtricitabine. Profiles Drug Subst Excip Relat Methodol. 2020;45:55-91. doi: 10.1016/bs.podrm.2019.10.003. Epub 2019 Dec 6. PMID: 32164970. |
| In vivo activity: | In this study, FDA-approved drugs lopinavir-ritonavir, hydroxychloroquine sulfate, and emtricitabine-tenofovir were tested against SARS-CoV-2 infection in a highly susceptible ferret infection model. While most of the drug treatments marginally reduced clinical symptoms, they did not reduce virus titers, with the exception of emtricitabine-tenofovir treatment, which led to diminished virus titers in nasal washes at 8 dpi. Further, the azathioprine-treated immunosuppressed ferrets showed delayed virus clearance and low SN titers, resulting in a prolonged infection. As several FDA-approved or repurposed drugs are being tested as antiviral candidates at clinics without sufficient information, rapid preclinical animal studies should proceed to identify therapeutic drug candidates with strong antiviral potential and high safety prior to a human efficacy trial. Reference: Park SJ, Yu KM, Kim YI, Kim SM, Kim EH, Kim SG, Kim EJ, Casel MAB, Rollon R, Jang SG, Lee MH, Chang JH, Song MS, Jeong HW, Choi Y, Chen W, Shin WJ, Jung JU, Choi YK. Antiviral Efficacies of FDA-Approved Drugs against SARS-CoV-2 Infection in Ferrets. mBio. 2020 May 22;11(3):e01114-20. doi: 10.1128/mBio.01114-20. PMID: 32444382; PMCID: PMC7244896. |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 30.0 | 121.33 | |
| DMF | 20.0 | 80.89 | |
| PBS(pH 7.2) | 5.0 | 20.22 |
The following data is based on the product molecular weight 247.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | Al-Majed AA, Bakheit AHH, Al-Qahtani BM, Al-Kahtani HM, Abdelhameed AS. Emtricitabine. Profiles Drug Subst Excip Relat Methodol. 2020;45:55-91. doi: 10.1016/bs.podrm.2019.10.003. Epub 2019 Dec 6. PMID: 32164970. |
| In vitro protocol: | Al-Majed AA, Bakheit AHH, Al-Qahtani BM, Al-Kahtani HM, Abdelhameed AS. Emtricitabine. Profiles Drug Subst Excip Relat Methodol. 2020;45:55-91. doi: 10.1016/bs.podrm.2019.10.003. Epub 2019 Dec 6. PMID: 32164970. |
| In vivo protocol: | Park SJ, Yu KM, Kim YI, Kim SM, Kim EH, Kim SG, Kim EJ, Casel MAB, Rollon R, Jang SG, Lee MH, Chang JH, Song MS, Jeong HW, Choi Y, Chen W, Shin WJ, Jung JU, Choi YK. Antiviral Efficacies of FDA-Approved Drugs against SARS-CoV-2 Infection in Ferrets. mBio. 2020 May 22;11(3):e01114-20. doi: 10.1128/mBio.01114-20. PMID: 32444382; PMCID: PMC7244896. |
1: Gantner P, Hessamfar M, Souala MF, Valin N, Simon A, Ajana F, Bouvet E, Rouveix E, Cotte L, Bani-Sadr F, Hustache-Mathieu L, Lebrette MG, Truchetet F, Galempoix JM, Piroth L, Pellissier G, Muret P, Rey D; E/C/F/TAF PEP Study Group. Elvitegravir-Cobicistat-Emtricitabine-Tenofovir Alafenamide Single-tablet Regimen for Human Immunodeficiency Virus Postexposure Prophylaxis. Clin Infect Dis. 2019 Jun 28. pii: ciz577. doi: 10.1093/cid/ciz577. [Epub ahead of print] PubMed PMID: 31804669.
2: Ascher SB, Scherzer R, Estrella MM, Shigenaga J, Spaulding KA, Glidden DV, Mehrotra ML, Defechereux P, Gandhi M, Grant RM, Shlipak MG, Jotwani V. HIV pre-exposure prophylaxis with tenofovir disoproxil fumarate/emtricitabine and changes in kidney function and tubular health. AIDS. 2019 Dec 2. doi: 10.1097/QAD.0000000000002456. [Epub ahead of print] PubMed PMID: 31794523.
3: Antoni G, Tremblay C, Delaugerre C, Charreau I, Cua E, Rojas Castro D, Raffi F, Chas J, Huleux T, Spire B, Capitant C, Cotte L, Meyer L, Molina JM; ANRS IPERGAY study group. On-demand pre-exposure prophylaxis with tenofovir disoproxil fumarate plus emtricitabine among men who have sex with men with less frequent sexual intercourse: a post-hoc analysis of the ANRS IPERGAY trial. Lancet HIV. 2019 Nov 26. pii: S2352-3018(19)30341-8. doi: 10.1016/S2352-3018(19)30341-8. [Epub ahead of print] PubMed PMID: 31784343.
4: Dickinson L, Gurjar R, Stöhr W, Bonora S, Owen A, D'Avolio A, Cursley A, Molina JM, Fäetkenheuer G, Vandekerckhove L, Di Perri G, Pozniak A, Richert L, Raffi F, Boffito M; NEAT001/ANRS143 Study Group . Population pharmacokinetics and pharmacogenetics of ritonavir-boosted darunavir in the presence of raltegravir or tenofovir disoproxil fumarate/emtricitabine in HIV-infected adults and the relationship with virological response: a sub-study of the NEAT001/ANRS143 randomized trial. J Antimicrob Chemother. 2019 Nov 21. pii: dkz479. doi: 10.1093/jac/dkz479. [Epub ahead of print] PubMed PMID: 31754703.
5: Stirrup OT, Sabin CA, Phillips AN, Williams I, Churchill D, Tostevin A, Hill T, Dunn DT; UK HIV Drug Resistance Database and the UK Collaborative HIV Cohort . Associations between baseline characteristics, CD4 cell count response and virological failure on first-line efavirenz + tenofovir + emtricitabine for HIV. J Virus Erad. 2019 Nov 4;5(4):204-211. PubMed PMID: 31754443; PubMed Central PMCID: PMC6844404.
6: Shieh E, Marzinke MA, Fuchs EJ, Hamlin A, Bakshi R, Aung W, Breakey J, Poteat T, Brown T, Bumpus NN, Hendrix CW. Transgender women on oral HIV pre-exposure prophylaxis have significantly lower tenofovir and emtricitabine concentrations when also taking oestrogen when compared to cisgender men. J Int AIDS Soc. 2019 Nov;22(11):e25405. doi: 10.1002/jia2.25405. PubMed PMID: 31692269; PubMed Central PMCID: PMC6832671.
7: Liu SN, Gufford BT, Lu JBL, Bushman LR, Anderson PL, Bergstrom RF, Desta Z, Gupta SK. Inhibitory Effects of Probenecid on Pharmacokinetics of Tenofovir Disoproxil Fumarate and Emtricitabine for On-Demand HIV Pre-Exposure Prophylaxis. Clin Pharmacol Ther. 2019 Nov 1. doi: 10.1002/cpt.1714. [Epub ahead of print] PubMed PMID: 31675437.
8: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548261/ PubMed PMID: 31643585.
9: Manickchund N, du Plessis C, John MA, Manzini TC, Gosnell BI, Lessells RJ, Moosa YS. Emtricitabine-induced pure red cell aplasia. South Afr J HIV Med. 2019 Sep 23;20(1):983. doi: 10.4102/sajhivmed.v20i1.983. eCollection 2019. PubMed PMID: 31616574; PubMed Central PMCID: PMC6779991.
10: Kityo C, Hagins D, Koenig E, Avihingsanon A, Chetchotisakd P, Supparatpinyo K, Gankina N, Pokrovsky V, Voronin E, Stephens JL, DeJesus E, Wang H, Acosta RK, Cao H, Quirk E, Martin H, Makadzange T. Switching to Fixed-Dose Bictegravir, Emtricitabine, and Tenofovir Alafenamide (B/F/TAF) in Virologically Suppressed HIV-1 Infected Women: A Randomized, Open-Label, Multicenter, Active-Controlled, Phase 3, Noninferiority Trial. J Acquir Immune Defic Syndr. 2019 Nov 1;82(3):321-328. doi: 10.1097/QAI.0000000000002137. PubMed PMID: 31609930.
11: Taramasso L, Di Biagio A, Riccardi N, Briano F, Di Filippo E, Comi L, Mora S, Giacomini M, Gori A, Maggiolo F. Lipid profile changings after switching from rilpivirine/tenofovir disoproxil fumarate/emtricitabine to rilpivirine/tenofovir alafenamide/emtricitabine: Different effects in patients with or without baseline hypercholesterolemia. PLoS One. 2019 Oct 11;14(10):e0223181. doi: 10.1371/journal.pone.0223181. eCollection 2019. PubMed PMID: 31603906; PubMed Central PMCID: PMC6788691.
12: Maggiolo F, Rizzardini G, Raffi F, Pulido F, Mateo-Garcia MG, Molina JM, Ong E, Shao Y, Piontkowsky D, Das M, McNicholl I, Haubrich R. Bone mineral density in virologically suppressed people aged 60 years or older with HIV-1 switching from a regimen containing tenofovir disoproxil fumarate to an elvitegravir, cobicistat, emtricitabine, and tenofovir alafenamide single-tablet regimen: a multicentre, open-label, phase 3b, randomised trial. Lancet HIV. 2019 Oct;6(10):e655-e666. doi: 10.1016/S2352-3018(19)30195-X. PubMed PMID: 31578954.
13: Andreatta K, Willkom M, Martin R, Chang S, Wei L, Liu H, Liu YP, Graham H, Quirk E, Martin H, White KL. Erratum to: Switching to bictegravir/emtricitabine/tenofovir alafenamide maintained HIV-1 RNA suppression in participants with archived antiretroviral resistance including M184V/I. J Antimicrob Chemother. 2019 Dec 1;74(12):3646-3647. doi: 10.1093/jac/dkz412. PubMed PMID: 31562501; PubMed Central PMCID: PMC6857191.
14: Yilmaz A, Mellgren Å, Fuchs D, Nilsson S, Blennow K, Zetterberg H, Gisslén M. Switching from a regimen containing abacavir/lamivudine or emtricitabine/tenofovir disoproxil fumarate to emtricitabine/tenofovir alafenamide fumarate does not affect central nervous system HIV-1 infection. Infect Dis (Lond). 2019 Nov - Dec;51(11-12):838-846. doi: 10.1080/23744235.2019.1670352. Epub 2019 Sep 26. PubMed PMID: 31556765.
15: Lu C, Yang Y, Zhang Q, Zhou R, Liu Z, Hu W. Pharmacokinetic and bioequivalence study of emtricitabine/tenofovir disoproxil fumarate tablets in healthy Chinese subjects. Int J Clin Pharmacol Ther. 2019 Dec;57(12):623-632. doi: 10.5414/CP203533. PubMed PMID: 31549623.
16: Lathouwers E, Wong EY, Brown K, Baugh B, Ghys A, Jezorwski J, Mohsine EG, Van Landuyt E, Opsomer M, De Meyer S; AMBER and EMERALD study groups. Week 48 Resistance Analyses of the Once-Daily, Single-Tablet Regimen Darunavir/Cobicistat/Emtricitabine/Tenofovir Alafenamide (D/C/F/TAF) in Adults Living with HIV-1 from the Phase III Randomized AMBER and EMERALD Trials. AIDS Res Hum Retroviruses. 2019 Oct 21. doi: 10.1089/AID.2019.0111. [Epub ahead of print] PubMed PMID: 31516033.
17: Ibrahim IM, Bade AN, Lin Z, Soni D, Wojtkiewicz M, Dyavar Shetty BL, Gautam N, McMillan JM, Alnouti Y, Edagwa BJ, Gendelman HE. Synthesis and characterization of a long-acting emtricitabine prodrug nanoformulation. Int J Nanomedicine. 2019 Aug 7;14:6231-6247. doi: 10.2147/IJN.S215447. eCollection 2019. PubMed PMID: 31496683; PubMed Central PMCID: PMC6689761.
18: Liu XI, Momper JD, Rakhmanina N, van den Anker JN, Green DJ, Burckart GJ, Best BM, Mirochnick M, Capparelli EV, Dallmann A. Physiologically Based Pharmacokinetic Models to Predict Maternal Pharmacokinetics and Fetal Exposure to Emtricitabine and Acyclovir. J Clin Pharmacol. 2019 Sep 6. doi: 10.1002/jcph.1515. [Epub ahead of print] PubMed PMID: 31489678.
19: Soni D, Bade AN, Gautam N, Herskovitz J, Ibrahim IM, Smith N, Wojtkiewicz MS, Dyavar Shetty BL, Alnouti Y, McMillan J, Gendelman HE, Edagwa BJ. Synthesis of a long acting nanoformulated emtricitabine ProTide. Biomaterials. 2019 Nov;222:119441. doi: 10.1016/j.biomaterials.2019.119441. Epub 2019 Aug 20. PubMed PMID: 31472458.
20: Huhn GD, Eron JJ, Girard PM, Orkin C, Molina JM, DeJesus E, Petrovic R, Luo D, Van Landuyt E, Lathouwers E, Nettles RE, Brown K, Wong EY. Darunavir/cobicistat/emtricitabine/tenofovir alafenamide in treatment-experienced, virologically suppressed patients with HIV-1: subgroup analyses of the phase 3 EMERALD study. AIDS Res Ther. 2019 Aug 29;16(1):23. doi: 10.1186/s12981-019-0235-1. PubMed PMID: 31464642; PubMed Central PMCID: PMC6716878.
