Tenofovir alafenamide fumarate (1:1 salt)
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MedKoo CAT#: 314271

CAS#: 379270-38-9 (fumarate)

Description: Tenofovir alafenamide, also known as TAF and GS-7340, is a nucleotide reverse transcriptase inhibitor (NRTIs) and a novel prodrug of tenofovir. By blocking reverse transcriptase, TAF prevent HIV from multiplying and can reduce the amount of HIV in the body. Tenofovir alafenamide is a prodrug, which means that it is an inactive drug. In the body, tenofovir alafenamide is converted to tenofovir diphosphate (TFV-DP). Tenofovir alafenamide fumarate was approved in November 2015 for treatment of HIV-1.


Chemical Structure

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Tenofovir alafenamide fumarate (1:1 salt)
CAS# 379270-38-9 (fumarate)

Theoretical Analysis

MedKoo Cat#: 314271
Name: Tenofovir alafenamide fumarate (1:1 salt)
CAS#: 379270-38-9 (fumarate)
Chemical Formula: C25H33N6O9P
Exact Mass:
Molecular Weight: 593.55
Elemental Analysis: C, 50.68; H, 5.61; N, 14.18; O, 24.30; P, 5.23

Price and Availability

Size Price Availability Quantity
200.0mg USD 150.0 Ready to ship
500.0mg USD 250.0 Ready to ship
1.0g USD 450.0 Ready to ship
2.0g USD 750.0 Ready to ship
5.0g USD 1650.0 Ready to ship
10.0g USD 2950.0 Ready to ship
50.0g USD 4950.0 2 Weeks
100.0g USD 8950.0 2 Weeks
200.0g USD 11450.0 2 Weeks
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Related CAS #: 379270-38-9 (fumarate)   1392275-56-7 (hemifumarate)   379270-37-8 (free base)  

Synonym: TAF; GS734; GS-734; GS 7340; Tenofovir alafenamide fumarate; trade name: Genvoya.

IUPAC/Chemical Name: (S)-isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate fumarate

InChi Key: MEJAFWXKUKMUIR-WIUYAKJJSA-N

InChi Code: InChI=1S/C21H29N6O5P.C4H4O4/c1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27;5-3(6)1-2-4(7)8/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24);1-2H,(H,5,6)(H,7,8)/b;2-1+/t15-,16+,33?;/m1./s1

SMILES Code: C[C@@H](C(OC(C)C)=O)N[P@@](OC1=CC=CC=C1)(CO[C@@H](CN2C=NC3=C(N=CN=C23)N)C)=O.O=C(/C=C/C(O)=O)O

Appearance: White to off-white 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 (30mg/mL)

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

Biological target: Tenofovir alafenamide fumarate (GS-7340 fumarate) is an investigational oral prodrug of Tenofovir, which is a HIV-1 nucleotide reverse transcriptase inhibitor.
In vitro activity: TAF regulated the differentiation, activation, and proliferation of hepatic stellate cells (HSCs). Furthermore, TAF suppressed the activities of TGFβ1/Smad3 and NF-κB/NLRP3 inflammasome signaling pathways in vitro. Nonstructural protein 5A transactivated protein 9 (NS5ATP9) inhibited liver fibrosis through TGFβ1/Smad3 and NF-κB signaling pathways. TAF upregulated the expression of NS5ATP9 in vitro. Finally, TAF could only show marginal therapeutic effects when NS5ATP9 was silenced and knocked out in vitro. Reference: Hepatol Int. 2020 Jan;14(1):145-160. https://pubmed.ncbi.nlm.nih.gov/31758498/
In vivo activity: To investigate the effects of TAF on BLM-induced pulmonary fibrosis, the mice were intragastrically administered with TAF (5.125 mg/kg) or vehicle once per day for 3 weeks on days 0, 7, and 14 after BLM injection at a dose of 2 mg/kg (Fig. 2a). The mice treated with BLM began to die on day 9, which agreed with the results of previous studies. Weight loss was lighter in TAF group, compared to BLM group (Fig. 2b). The mortality rate was 40–50% on days 21, 28, and 35 in the different BLM groups; in comparison, the mortality rate was 0–20% in mice treated with TAF (Fig. 2c) during the treatment period. Additionally, compared to mice treated with TAF on days 7 and 14 after administration of BLM, the mice treated with TAF starting on day 0 showed significant improvement in their survival rate and body weight loss. Reference: Respir Res. 2019; 20: 163. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6647111/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 68.0 114.56
Ethanol 100.0 168.48
Water 17.5 29.48

Preparing Stock Solutions

The following data is based on the product molecular weight 593.55 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.

Recalculate based on batch purity %
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: 1. Margot NA, Johnson A, Miller MD, Callebaut C. Characterization of HIV-1 Resistance to Tenofovir Alafenamide In Vitro. Antimicrob Agents Chemother. 2015 Oct;59(10):5917-24. doi: 10.1128/AAC.01151-15. Epub 2015 Jul 6. PMID: 26149983; PMCID: PMC4576099. 2. Callebaut C, Stepan G, Tian Y, Miller MD. In Vitro Virology Profile of Tenofovir Alafenamide, a Novel Oral Prodrug of Tenofovir with Improved Antiviral Activity Compared to That of Tenofovir Disoproxil Fumarate. Antimicrob Agents Chemother. 2015 Oct;59(10):5909-16. doi: 10.1128/AAC.01152-15. Epub 2015 Jul 6. PMID: 26149992; PMCID: PMC4576064. 3. Li L, Zhao J, Zhou L, Chen J, Ma Y, Yu Y, Cheng J. Tenofovir alafenamide fumarate attenuates bleomycin-induced pulmonary fibrosis by upregulating the NS5ATP9 and TGF-β1/Smad3 signaling pathway. Respir Res. 2019 Jul 22;20(1):163. doi: 10.1186/s12931-019-1102-2. PMID: 31331325; PMCID: PMC6647111. 4. Gunawardana M, Remedios-Chan M, Miller CS, Fanter R, Yang F, Marzinke MA, Hendrix CW, Beliveau M, Moss JA, Smith TJ, Baum MM. Pharmacokinetics of long-acting tenofovir alafenamide (GS-7340) subdermal implant for HIV prophylaxis. Antimicrob Agents Chemother. 2015 Jul;59(7):3913-9. doi: 10.1128/AAC.00656-15. Epub 2015 Apr 20. PMID: 25896688; PMCID: PMC4468692.
In vitro protocol: 1. Margot NA, Johnson A, Miller MD, Callebaut C. Characterization of HIV-1 Resistance to Tenofovir Alafenamide In Vitro. Antimicrob Agents Chemother. 2015 Oct;59(10):5917-24. doi: 10.1128/AAC.01151-15. Epub 2015 Jul 6. PMID: 26149983; PMCID: PMC4576099. 2. Callebaut C, Stepan G, Tian Y, Miller MD. In Vitro Virology Profile of Tenofovir Alafenamide, a Novel Oral Prodrug of Tenofovir with Improved Antiviral Activity Compared to That of Tenofovir Disoproxil Fumarate. Antimicrob Agents Chemother. 2015 Oct;59(10):5909-16. doi: 10.1128/AAC.01152-15. Epub 2015 Jul 6. PMID: 26149992; PMCID: PMC4576064.
In vivo protocol: 1. Li L, Zhao J, Zhou L, Chen J, Ma Y, Yu Y, Cheng J. Tenofovir alafenamide fumarate attenuates bleomycin-induced pulmonary fibrosis by upregulating the NS5ATP9 and TGF-β1/Smad3 signaling pathway. Respir Res. 2019 Jul 22;20(1):163. doi: 10.1186/s12931-019-1102-2. PMID: 31331325; PMCID: PMC6647111. 2. Gunawardana M, Remedios-Chan M, Miller CS, Fanter R, Yang F, Marzinke MA, Hendrix CW, Beliveau M, Moss JA, Smith TJ, Baum MM. Pharmacokinetics of long-acting tenofovir alafenamide (GS-7340) subdermal implant for HIV prophylaxis. Antimicrob Agents Chemother. 2015 Jul;59(7):3913-9. doi: 10.1128/AAC.00656-15. Epub 2015 Apr 20. PMID: 25896688; PMCID: PMC4468692.

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1: Shafran SD, Di Perri G, Esser S, Lelièvre JD, Parczewski M. Planning HIV therapy to prevent future comorbidities: patient years for tenofovir alafenamide. HIV Med. 2019 Jun;20 Suppl 7:1-16. doi: 10.1111/hiv.12755. Review. PubMed PMID: 31099116.

2: Bictegravir/emtricitabine/tenofovir alafenamide for HIV infection. Aust Prescr. 2019 Apr;42(2):68-69. doi: 10.18773/austprescr.2019.016. Epub 2019 Feb 28. Review. PubMed PMID: 31048941; PubMed Central PMCID: PMC6478953.

3: Common Drug Review New Combination Product Submission: Darunavir/Cobicistat/Emtricitabine/Tenofovir alafenamide (Symtuza): (Janssen Canada Inc.): Indication: A complete regimen for the treatment of HIV type 1 infection in adults and adolescents (aged 12 years and older with body weight at least 40 kg) with no known mutations associated with resistance to the individual components of Symtuza [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Aug. Available from http://www.ncbi.nlm.nih.gov/books/NBK540525/ PubMed PMID: 31034191.

4: CADTH Canadian Drug Expert Committee Recommendation: Darunavir/Cobicistat/Emtricitabine/Tenofovir Alafenamide (Symtuza — Janssen Inc.): Indication: Treatment of HIV type 1 (HIV-1) infection [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Jul. No abstract available. Available from http://www.ncbi.nlm.nih.gov/books/NBK540287/ PubMed PMID: 31013021.

5: Clinical Review Report: Bictegravir/Emtricitabine/Tenofovir Alafenamide (B/FTC/TAF) (Biktarvy): (Gilead Sciences Canada, Inc.): Indication: A complete regimen for the treatment of HIV-1 infection in adults with no known substitution associated with resistance to the individual components of Biktarvy [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Oct. Available from http://www.ncbi.nlm.nih.gov/books/NBK539526/ PubMed PMID: 30958669.

6: Pharmacoeconomic Review Report: Bictegravir/Emtricitabine/Tenofovir Alafenamide (B/FTC/TAF) (Biktarvy): (Gilead Sciences Canada, Inc.): Indication: A complete regimen for the treatment of HIV-1 infection in adults with no known substitution associated with resistance the individual components of Biktarvy [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Oct. Available from http://www.ncbi.nlm.nih.gov/books/NBK539546/ PubMed PMID: 30958667.

7: CADTH Canadian Drug Expert Committee Recommendation: Bictegravir/Emtricitabine/Tenofovir Alafenamide (Biktarvy — Gilead Sciences Canada, Inc.): Indication: As a complete regimen for the treatment of human immunodeficiency virus-1 (HIV-1) infection in adults with no known substitution associated with resistance to the individual components of Biktarvy [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Oct. No abstract available. Available from http://www.ncbi.nlm.nih.gov/books/NBK539326/ PubMed PMID: 30942994.

8: Pharmacoeconomic Review Report: Emtricitabine/tenofovir alafenamide (Descovy) [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2016 Aug. Available from http://www.ncbi.nlm.nih.gov/books/NBK539225/ PubMed PMID: 30933443.

9: Clinical Review Report: Emtricitabine/tenofovir alafenamide fumarate (Descovy) [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2016 Aug. Available from http://www.ncbi.nlm.nih.gov/books/NBK538758/ PubMed PMID: 30883070.

10: CADTH Canadian Drug Expert Committee Final Recommendation: Emtricitabine/Tenofovir Alafenamide: (Descovy — Gilead Sciences Canada, Inc.): Indication: HIV-1 Infection [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2016 Aug. No abstract available. Available from http://www.ncbi.nlm.nih.gov/books/NBK538372/ PubMed PMID: 30860687.

11: Pham HT, Mesplède T. Bictegravir in a fixed-dose tablet with emtricitabine and tenofovir alafenamide for the treatment of HIV infection: pharmacology and clinical implications. Expert Opin Pharmacother. 2019 Mar;20(4):385-397. doi: 10.1080/14656566.2018.1560423. Epub 2019 Jan 30. Review. PubMed PMID: 30698467.

12: Giacomet V, Cossu MV, Capetti AF, Zuccotti G, Rizzardini G. An evaluation of elvitegravir plus cobicistat plus tenofovir alafenamide plus emtricitabine as a single-tablet regimen for the treatment of HIV in children and adolescents. Expert Opin Pharmacother. 2019 Feb;20(3):269-276. doi: 10.1080/14656566.2018.1559299. Epub 2018 Dec 26. Review. PubMed PMID: 30586314.

13: Clinical Review Report: Tenofovir Alafenamide (Vemlidy): (Gilead Sciences Canada, Inc.): Indication: Treatment of chronic hepatitis B in adults with compensated liver disease [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Apr. Available from http://www.ncbi.nlm.nih.gov/books/NBK533926/ PubMed PMID: 30475544.

14: Hill L, Smith SR, Karris MY. Profile of bictegravir/emtricitabine/tenofovir alafenamide fixed dose combination and its potential in the treatment of HIV-1 infection: evidence to date. HIV AIDS (Auckl). 2018 Oct 29;10:203-213. doi: 10.2147/HIV.S145529. eCollection 2018. Review. PubMed PMID: 30464641; PubMed Central PMCID: PMC6214311.

15: Squillace N, Bozzi G, Colella E, Gori A, Bandera A. Darunavir-cobicistat-emtricitabine-tenofovir alafenamide: safety and efficacy of a protease inhibitor in the modern era. Drug Des Devel Ther. 2018 Oct 29;12:3635-3643. doi: 10.2147/DDDT.S147493. eCollection 2018. Review. PubMed PMID: 30464395; PubMed Central PMCID: PMC6211373.

16: Deeks ED. Bictegravir/Emtricitabine/Tenofovir Alafenamide: A Review in HIV-1 Infection. Drugs. 2018 Nov;78(17):1817-1828. doi: 10.1007/s40265-018-1010-7. Review. Erratum in: Drugs. 2019 Mar 22;:. PubMed PMID: 30460547; PubMed Central PMCID: PMC6424950.

17: Pharmacoeconomic Review Report: Tenofovir Alafenamide (Vemlidy): (Gilead Sciences Canada, Inc.): Indication: Treatment of chronic hepatitis B in adults with compensated liver disease [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Apr. Available from http://www.ncbi.nlm.nih.gov/books/NBK532825/ PubMed PMID: 30427623.

18: CADTH Canadian Drug Expert Committee Recommendation: Tenofovir Alafenamide (Vemlidy - Gilead Sciences Canada, Inc.): Indication: Chronic Hepatitis B [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2018 Mar 28. No abstract available. Available from http://www.ncbi.nlm.nih.gov/books/NBK532703/ PubMed PMID: 30403460.

19: Childs-Kean LM, Egelund EF, Jourjy J. Tenofovir Alafenamide for the Treatment of Chronic Hepatitis B Monoinfection. Pharmacotherapy. 2018 Oct;38(10):1051-1057. doi: 10.1002/phar.2174. Epub 2018 Sep 9. Review. PubMed PMID: 30120841.

20: Byrne R, Carey I, Agarwal K. Tenofovir alafenamide in the treatment of chronic hepatitis B virus infection: rationale and clinical trial evidence. Therap Adv Gastroenterol. 2018 Jul 16;11:1756284818786108. doi: 10.1177/1756284818786108. eCollection 2018. Review. PubMed PMID: 30034532; PubMed Central PMCID: PMC6048601.



Additional Information

Related CAS#
CAS#379270-38-9 =Tenofovir alafenamide fumarate, 1:1
CAS#1392275-56-7= Tenofovir alafenamide hemifumarate, 2:1
CAS#379270-37-8 = Tenofovir alafenamide